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Also known as: 1628732-62-6, Olinciguat [inn], Iw-1701, Olinciguat [usan], Iw1701, Pd5f4zxd21

Molecular Formula

C₂₁H₁₆F₅N₇O₃

Molecular Weight

509.4 g/mol

InChI Key

YWQFJNWMWZMXRW-HXUWFJFHSA-N

FDA UNII

PD5F4ZXD21

Olinciguat is an orally bioavailable stimulator of soluble guanylate cyclase (sGC), with potential anti-inflammatory and vasodilating activities. Upon oral administration, olinciguat targets, allosterically binds to and enhances the nitric oxide (NO)-dependent catalytic activity of sGC. This enhances NO-sGC signaling and increases the formation of the intracellular second messenger cyclic guanosine monophosphate (cGMP), which is derived from guanosine triphosphate (GTP). This enhances NO/cGMP-mediated muscle relaxation, suppresses leukocyte-endothelial interactions and promotes vascular anti-inflammatory effects. The NO/sGC/cGMP signaling pathway plays an important role in vasodilation, blood flow and inflammatory processes. sGC, a heme-containing cytoplasmic signaling enzyme, catalyzes the formation of cGMP from GTP in response to NO binding to heme.

1 2D Structure

Olinciguat

2 Identification

2.1 Computed Descriptors

2.1.1 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-yl]amino]methyl]-2-hydroxypropanamide

2.1.2 InChI

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

2.1.3 InChI Key

YWQFJNWMWZMXRW-HXUWFJFHSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

PD5F4ZXD21

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1628732-62-6

2. Olinciguat [inn]

3. Iw-1701

4. Olinciguat [usan]

5. Iw1701

6. Pd5f4zxd21

7. (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

8. Olinciguat (usan/inn)

9. Olinciguat [usan:inn]

10. Unii-pd5f4zxd21

11. Olinciguat [who-dd]

12. Chembl4297616

13. Schembl16081945

14. Gtpl10213

15. Bdbm321744

16. Db15238

17. Iw-1701iw-1701

18. Us10183021, Compound I-531

19. Ac-31551

20. Hy-109066

21. Cs-0033431

22. D11475

23. D87219

24. (2~{r})-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

25. (2r)-3,3,3-trifluoro-2-(((5-fluoro-2-(1-((2-fluorophenyl)methyl)-5-(1,2-oxazol-3-yl)-1h-pyrazol-3-yl)pyrimidin-4-yl)amino)methyl)-2-hydroxypropanamide

26. Propanamide, 3,3,3-trifluoro-2-(((5-fluoro-2-(1-((2-fluorophenyl)methyl)-5-(3-isoxazolyl)-1h-pyrazol-3-yl)-4-pyrimidinyl)amino)methyl)-2-hydroxy-, (2r)-

2.4 Create Date

2015-02-13

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₆F₅N₇O₃
Molecular Weight	509.4 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	8
Exact Mass	509.12347821 g/mol
Monoisotopic Mass	509.12347821 g/mol
Topological Polar Surface Area	145 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	768
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1