From Wikipedia, the free encyclopedia
Chemical compound
Olinciguat
![](https://upload.wikimedia.org/wikipedia/commons/thumb/1/13/Olinciguat.svg/220px-Olinciguat.svg.png) |
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Other names | IW-1701 |
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(2R)-3,3,3-Trifluoro-2-[[[5-fluoro-2-[1-[(2-fluorophenyl)methyl]-5-(1,2-oxazol-3-yl)pyrazol-3-yl]pyrimidin-4-yl]amino]methyl]-2-hydroxypropanamide
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Formula | C21H16F5N7O3 |
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Molar mass | 509.397 g·mol−1 |
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3D model (
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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
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InChI=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 Key:YWQFJNWMWZMXRW-HXUWFJFHSA-N
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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]
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^ Buys, E. S.; Zimmer, D. P.; Chickering, J.; Graul, R.; Chien, Y. T.; Profy, A.; Hadcock, J. R.; Masferrer, J. L.; Milne, G. T. (1 August 2018).
"Discovery and development of next generation sGC stimulators with diverse multidimensional pharmacology and broad therapeutic potential". Nitric Oxide. 78: 72–80.
doi:
10.1016/j.niox.2018.05.009.
ISSN
1089-8603.
PMID
29859918.
S2CID
44149174.
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^ 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. (September 2021).
"Olinciguat, a stimulator of soluble guanylyl cyclase, attenuates inflammation, vaso-occlusion and nephropathy in mouse models of sickle cell disease". British Journal of Pharmacology. 178 (17): 3463–3475.
doi:
10.1111/bph.15492.
ISSN
1476-5381.
PMC
8453770.
PMID
33864386.
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^ 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. (8 April 2020).
"Olinciguat, an Oral sGC Stimulator, Exhibits Diverse Pharmacology Across Preclinical Models of Cardiovascular, Metabolic, Renal, and Inflammatory Disease". Frontiers in Pharmacology. 11: 419.
doi:
10.3389/fphar.2020.00419.
ISSN
1663-9812.
PMC
7156612.
PMID
32322204.
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^
"Ironwood Pharmaceuticals Announces FDA Orphan Drug Designation for Olinciguat for the Treatment of Sickle Cell Disease". investor.ironwoodpharma.com. Retrieved 8 November 2023.
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^ PhD, Joana Carvalho (20 October 2020).
"Cyclerion Suspends Development of Olinciguat for Sickle Cell Disease". sicklecellanemianews.com. Retrieved 8 November 2023.