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    pharmacompass-2-m-2025-10-20

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    Olinciguat

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 509.4 g/mol
    Molecular Formula C21H16F5N7O3
    XLogP32.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count8
    Exact Mass509.12347821 g/mol
    Monoisotopic Mass509.12347821 g/mol
    Topological Polar Surface Area145 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity768
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of sickle cell disease