X0306 4 2019-08-30 0 0001446847 IRONWOOD PHARMACEUTICALS INC IRWD 0001478448 MCCOURT Thomas A C/O IRONWOOD PHARMACEUTICALS, INC. 301 BINNEY STREET CAMBRIDGE MA 02142 0 1 0 0 President Class A Common Stock 2019-08-30 4 M 0 90000 4.88 A 199739 D Class A Common Stock 2019-08-30 4 M 0 130000 4.88 A 329739 D Class A Common Stock 2019-08-30 4 S 0 220000 9.24 D 109739 D Employee Stock Option (Right to Buy) 4.88 2019-08-30 4 M 0 90000 0.00 D 2019-09-07 Class A Common Stock 90000 44944 D Employee Stock Option (Right to Buy) 4.88 2019-08-30 4 M 0 130000 0.00 D 2019-09-07 Class A Common Stock 130000 0 D The reporting person acquired 2,500 shares of Class A common stock under the issuer's employee stock purchase plan on June 28, 2019. This sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person. The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $9.12 to $9.40, 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. This option vested as to 40,000 shares of Class A common stock on each of October 24, 2011, December 21, 2012 and January 4, 2017 upon the issuer's achievement of regulatory or commercial milestones. The remainder of the option expires on September 7, 2019. This option, granted as an annual performance award, is presently exercisable in full. /s/ Conor Kilroy, Attorney-in-Fact 2019-09-04