IRWD

SEC source: 0001209191-19-023457 · doc4.xml · nonDerivative · entry 1

Duane Jon R · CIK 0001772129 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,995

F1 · kind: Issued pursuant to the Director Compensation Plan, effective as of January 2014.

SEC source: 0001209191-19-023431 · doc4.xml · derivative · entry 6

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 42,472

Underlying: Class A Common Stock · 2,472 shares

Expires 2019-07-28

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F7 · derivative.exercise_date: The option has vested as to 20,000 shares as of the date hereof. The remaining shares will vest upon the issuer's achievement of a certain milestone.

SEC source: 0001209191-19-023431 · doc4.xml · derivative · entry 5

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 161,804

Underlying: Class A Common Stock · 16,804 shares

Expires 2029-01-29

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F6 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2019.

SEC source: 0001209191-19-023431 · doc4.xml · derivative · entry 4

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 75,949

Underlying: Class A Common Stock · 5,949 shares

Expires 2028-02-21

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F5 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2018.

SEC source: 0001209191-19-023431 · doc4.xml · derivative · entry 3

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 84,326

Underlying: Class A Common Stock · 4,326 shares

Expires 2027-02-27

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F4 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2017.

SEC source: 0001209191-19-023431 · doc4.xml · derivative · entry 2

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 66,506

Underlying: Class A Common Stock · 1,506 shares

Expires 2026-03-01

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F3 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2016.

SEC source: 0001209191-19-023431 · doc4.xml · nonDerivative · entry 1

Gilbert Halley E · CIK 0001601360 · Chief Admin Officer & SVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 242,295

F1 · price: In connection with the separation (the "Separation") of Cyclerion Therapeutics, Inc. ("Cyclerion") from Ironwood Pharmaceuticals, Inc. ("Ironwood"), the reporting person received 17,165 restricted stock units as a result of the adjustment of existing Ironwood restricted stock units held by the reporting person prior to the Separation. The restricted stock units are subject to vesting conditions consistent with the terms of the existing Ironwood restricted stock units held by the reporting person prior to the Separation.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 7

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 161,804

Underlying: Class A Common Stock · 16,804 shares

Expires 2029-01-29

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F8 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2019.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 6

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,099

Underlying: Class A Common Stock · 5,099 shares

Expires 2028-02-21

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F7 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2018.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 5

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,236

Underlying: Class A Common Stock · 1,236 shares

Expires 2028-01-02

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F6 · derivative.exercise_date: The option, granted as a promotion award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of November 27, 2017.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 4

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 30,695

Underlying: Class A Common Stock · 695 shares

Expires 2026-03-01

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F5 · derivative.exercise_date: The option, granted as an annual performance award, vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of January 1, 2016.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 3

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,077

Underlying: Class A Common Stock · 77 shares

Expires 2025-09-16

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F4 · derivative.exercise_date: The option vests as to 2.08333% of the shares of Class A Common Stock on each monthly anniversary of September 16, 2015.

SEC source: 0001209191-19-023430 · doc4.xml · derivative · entry 2

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 43,563

Underlying: Class A Common Stock · 3,563 shares

Expires 2024-07-01

F2 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F2 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the number of shares subject to this option and the exercise price have been adjusted, and the reporting person received options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the existing Ironwood option award.

F3 · derivative.exercise_date: This option, granted as a new hire award, is presently exercisable in full.

SEC source: 0001209191-19-023430 · doc4.xml · nonDerivative · entry 1

Consylman Gina · CIK 0001546358 · SVP, CFO & Treasurer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 179,915

F1 · price: In connection with the separation (the "Separation") of Cyclerion Therapeutics, Inc. ("Cyclerion") from Ironwood Pharmaceuticals, Inc. ("Ironwood"), the reporting person received 16,731 restricted stock units as a result of the adjustment of existing Ironwood restricted stock units held by the reporting person prior to the Separation. The restricted stock units are subject to vesting conditions consistent with the terms of the existing Ironwood restricted stock units held by the reporting person prior to the Separation.

SEC source: 0001209191-19-023429 · doc4.xml · derivative · entry 4

Huyett William · CIK 0001723846 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 16,171

Underlying: Class A Common Stock · 242,579 shares

Expires 2029-01-29

F3 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F3 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F3 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F5 · derivative.exercise_date: The remaining 16,171 shares are presently exercisable in full.

SEC source: 0001209191-19-023429 · doc4.xml · derivative · entry 3

Huyett William · CIK 0001723846 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 105,468

Underlying: Class A Common Stock · 232,032 shares

Expires 2028-01-02

F3 · derivative.exercise_price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F3 · shares: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F3 · price: Represents options to purchase Ironwood Class A Common Stock awarded to the reporting person prior to the Separation. In connection with the Separation, the unvested portion of the Ironwood option award was replaced with options to purchase shares of Cyclerion Common Stock. The exercise price of the vested portion of the Ironwood option award has been adjusted, and the reporting person received additional options to purchase shares of Cyclerion Common Stock, to preserve the pre-Separation intrinsic value of the vested portion of the Ironwood option award.

F4 · derivative.exercise_date: The remaining 105,468 shares are presently exercisable in full.

SEC source: 0001209191-19-023429 · doc4.xml · nonDerivative · entry 2

Huyett William · CIK 0001723846 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 27,546

F2 · price: In connection with the Separation, the reporting person received 1,483 restricted stock units as a result of the adjustment of existing Ironwood restricted stock units held by the reporting person prior to the Separation. This award vests as shares of Class A Common Stock on May 9, 2019.

SEC source: 0001209191-19-023429 · doc4.xml · nonDerivative · entry 1

Huyett William · CIK 0001723846 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 26,063

F1 · price: Represents the disposition of 85,312 restricted stock units in connection with the separation (the "Separation") of Cyclerion Therapeutics, Inc. ("Cyclerion") from Ironwood Pharmaceuticals, Inc. ("Ironwood") in exchange for restricted stock units representing the right to receive shares of Cyclerion Common Stock.

SEC source: 0001209191-19-023423 · doc4.xml · nonDerivative · entry 1

WILLIAMS DOUGLAS E · CIK 0001184847 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 87,800

F1 · price: Represents the forfeiture of 4,056 shares of restricted stock in connection with the reporting person's transition off of the Board of Directors of Ironwood Pharmaceuticals, Inc.

SEC source: 0001209191-19-023419 · doc4.xml · nonDerivative · entry 1

SCHULMAN AMY W · CIK 0001438226 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 38,242

F1 · price: Represents the disposition of 4,056 shares of restricted stock in connection with the separation of Cyclerion Therapeutics, Inc. ("Cyclerion") from Ironwood Pharmaceuticals, Inc. in exchange for restricted shares of Cyclerion Common Stock.

SEC source: 0001209191-19-023411 · doc4.xml · nonDerivative · entry 1

Fanucci Marsha · CIK 0001298814 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 132,663

F1 · price: Represents the disposition of 4,056 shares of restricted stock in connection with the separation of Cyclerion Therapeutics, Inc. ("Cyclerion") from Ironwood Pharmaceuticals, Inc. in exchange for restricted shares of Cyclerion Common Stock.

SEC source: 0001209191-19-020268 · doc4.xml · nonDerivative · entry 1

MCGUIRE TERRANCE · CIK 0001117003 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 77,686

F1 · kind: Issued pursuant to the Director Compensation Plan, effective as of January 2014.

SEC source: 0001209191-19-020265 · doc4.xml · nonDerivative · entry 1

SCHULMAN AMY W · CIK 0001438226 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 42,298

F1 · kind: Issued pursuant to the Director Compensation Plan, effective as of January 2014.

SEC source: 0001209191-19-018232 · doc4.xml · nonDerivative · entry 2

Currie Mark G · CIK 0001478244 · Chief Scientific Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 528,480

F1 · kind: Mark Currie sold the shares of common stock of Ironwood Pharmaceuticals, Inc. to raise proceeds to fund a portion of his commitment to purchase shares of common stock of Cyclerion Therapeutics, Inc. alongside other investors in a private placement.

F3 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.04 to $13.39, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-018232 · doc4.xml · nonDerivative · entry 1

Currie Mark G · CIK 0001478244 · Chief Scientific Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 577,980

F1 · kind: Mark Currie sold the shares of common stock of Ironwood Pharmaceuticals, Inc. to raise proceeds to fund a portion of his commitment to purchase shares of common stock of Cyclerion Therapeutics, Inc. alongside other investors in a private placement.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $12.94 to $13.45, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-017305 · doc4.xml · nonDerivative · entry 1

McHugh Julie · CIK 0001487179 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 88,131

F1 · kind: This sale was executed pursuant to a Rule 10b5-1 trading plan adopted by the reporting person and was effected to cover tax withholding obligations in connection with the vesting of the reporting person's director restricted stock awards.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.16 to $14.65, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-017525 · doc4.xml · nonDerivative · entry 1

Hecht Peter M · CIK 0001478485 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,217,366

F1 · kind: On March 5, 2019, Peter M. Hecht donated the shares of common stock of Ironwood Pharmaceuticals, Inc. to a donor advised fund.

SEC source: 0001209191-19-017301 · doc4.xml · nonDerivative · entry 1

OLANOFF LAWRENCE S · CIK 0001224341 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 37,553

F1 · kind: This sale was executed pursuant to a Rule 10b5-1 trading plan adopted by the reporting person and was effected to cover tax withholding obligations in connection with the vesting of the reporting person's director restricted stock awards.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.16 to $14.67, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 6

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 83,309

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F5 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 5

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 83,323

F3 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F5 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 4

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 83,340

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F5 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012637 · doc4.xml · nonDerivative · entry 2

Currie Mark G · CIK 0001478244 · Chief Scientific Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 803,480

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F3 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 8

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,130

F5 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 7

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,152

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 6

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,177

F3 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 1, 2016.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 5

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,197

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 8

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,184

F5 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 7

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,202

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 6

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,219

F3 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 1, 2016.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 5

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,228

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F6 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.24 to $14.38, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 3

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 83,350

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 2

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 84,981

F3 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012651 · doc4.xml · nonDerivative · entry 1

MCCOURT Thomas A · CIK 0001478448 · Chief Commercial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 86,938

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012637 · doc4.xml · nonDerivative · entry 1

Currie Mark G · CIK 0001478244 · Chief Scientific Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 803,493

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 4

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,215

F5 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 3

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 227,824

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 2

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 230,806

F3 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 1, 2016.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012643 · doc4.xml · nonDerivative · entry 1

Gilbert Halley E · CIK 0001601360 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 233,229

F1 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on March 16, 2015.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 4

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,230

F5 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 21, 2018.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

SEC source: 0001209191-19-012630 · doc4.xml · nonDerivative · entry 3

Consylman Gina · CIK 0001546358 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 165,467

F4 · shares: This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. This sale was made to cover tax withholding obligations in connection with the vesting and settlement of approximately 25% of the reporting person's restricted stock units granted on February 27, 2017.

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $14.12 to $14.59, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.