Olinciguat Explained

Legal Status:

Investigational

Cas Number:

1628732-62-6

Pubchem:

90445883

Chemspiderid:

64835205

Drugbank:

DB15238

Iuphar Ligand:

10213

Synonyms:

IW-1701

Chembl:

4297616

Kegg:

D11475

Unii:

PD5F4ZXD21

Stdinchi:

1S/C21H16F5N7O3/c22-12-4-2-1-3-11(12)9-33-16(14-5-6-36-32-14)7-15(31-33)18-28-8-13(23)17(30-18)29-10-20(35,19(27)34)21(24,25)26/h1-8,35H,9-10H2,(H2,27,34)(H,28,29,30)/t20-/m1/s1

Stdinchikey:

YWQFJNWMWZMXRW-HXUWFJFHSA-N

Smiles:

C1=CC=C(C(=C1)CN2C(=CC(=N2)C3=NC=C(C(=N3)NC[C@@](C(=O)N)(C(F)(F)F)O)F)C4=NOC=C4)F

Iupac Name:

(2R)-3,3,3-Trifluoro-2-5-fluoro-2-[1-[(2-fluorophenyl)methyl]-5-(1,2-oxazol-3-yl)pyrazol-3-yl]pyrimidin-4-ylamino]methyl]-2-hydroxypropanamide| C = 21 | H = 16 | F = 5 | N = 7 | O = 3}}

Olinciguat (IW-1701) is a soluble guanylate cyclase stimulator that was in development for sickle cell anemia.^{[1] [2] [3]} After receiving orphan drug status in 2018^[4] and completing a phase II trial, its development for sickle cell anemia was discontinued in 2020.^[5]

References

Notes and References

1. Buys . E. S. . Zimmer . D. P. . Chickering . J. . Graul . R. . Chien . Y. T. . Profy . A. . Hadcock . J. R. . Masferrer . J. L. . Milne . G. T. . Discovery and development of next generation sGC stimulators with diverse multidimensional pharmacology and broad therapeutic potential . Nitric Oxide . 1 August 2018 . 78 . 72–80 . 10.1016/j.niox.2018.05.009 . 29859918 . 44149174 . 1089-8603. free .
2. Tchernychev . Boris . Li . Huihui . Lee . Sung-Kyun . Gao . Xin . Ramanarasimhaiah . Raghunath . Liu . Guang . Hall . Katherine C. . Bernier . Sylvie G. . Jones . Juli E. . Feil . Susanne . Feil . Robert . Buys . Emmanuel S. . Graul . Regina M. . Frenette . Paul S. . Masferrer . Jaime L. . Olinciguat, a stimulator of soluble guanylyl cyclase, attenuates inflammation, vaso-occlusion and nephropathy in mouse models of sickle cell disease . British Journal of Pharmacology . September 2021 . 178 . 17 . 3463–3475 . 10.1111/bph.15492 . 33864386 . 8453770 . 1476-5381.
3. Zimmer . Daniel P. . Shea . Courtney M. . Tobin . Jenny V. . Tchernychev . Boris . Germano . Peter . Sykes . Kristie . Banijamali . Ali R. . Jacobson . Sarah . Bernier . Sylvie G. . Sarno . Renee . Carvalho . Andrew . Chien . Yueh-tyng . Graul . Regina . Buys . Emmanuel S. . Jones . Juli E. . Wakefield . James D. . Price . Gavrielle M. . Chickering . Jennifer G. . Milne . G. Todd . Currie . Mark G. . Masferrer . Jaime L. . Olinciguat, an Oral sGC Stimulator, Exhibits Diverse Pharmacology Across Preclinical Models of Cardiovascular, Metabolic, Renal, and Inflammatory Disease . Frontiers in Pharmacology . 8 April 2020 . 11 . 419 . 10.3389/fphar.2020.00419 . 32322204 . 7156612 . 1663-9812 . free .
4. Web site: Ironwood Pharmaceuticals Announces FDA Orphan Drug Designation for Olinciguat for the Treatment of Sickle Cell Disease . investor.ironwoodpharma.com . 8 November 2023.
5. Web site: PhD . Joana Carvalho . Cyclerion Suspends Development of Olinciguat for Sickle Cell Disease . sicklecellanemianews.com . 8 November 2023 . 20 October 2020.