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    LAROPIPRANT

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: 571170-77-9, Mk 0524, Mk-0524, Cardaptive, Cordaptive, Chembl426559
    Molecular Formula
    C21H19ClFNO4S
    Molecular Weight
    435.9  g/mol
    InChI Key
    NXFFJDQHYLNEJK-CYBMUJFWSA-N
    FDA UNII
    G7N11T8O78
    Laropiprant is a prostaglandin D2 receptor (DP1) antagonist with niacin-induced vasodilation inhibiting activity. Laropiprant binds to and inhibits the activity of DP1, a G-protein coupled receptor. Via competing with prostaglandin D2 (PG D2) for binding to DP1, this agent prevents PG D2-induced vasodilation and increased blood flow. As niacin induces the synthesis of PG D2, predominantly in the skin, administration of laropiprant may prevent niacin-induced vasodilation in the skin and facial flushing.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
    2.1.2 InChI
    InChI=1S/C21H19ClFNO4S/c1-29(27,28)18-10-15(23)9-17-16-7-4-13(8-19(25)26)20(16)24(21(17)18)11-12-2-5-14(22)6-3-12/h2-3,5-6,9-10,13H,4,7-8,11H2,1H3,(H,25,26)/t13-/m1/s1
    2.1.3 InChI Key
    NXFFJDQHYLNEJK-CYBMUJFWSA-N
    2.1.4 Canonical SMILES
    CS(=O)(=O)C1=CC(=CC2=C1N(C3=C2CCC3CC(=O)O)CC4=CC=C(C=C4)Cl)F
    2.1.5 Isomeric SMILES
    CS(=O)(=O)C1=CC(=CC2=C1N(C3=C2CC[C@@H]3CC(=O)O)CC4=CC=C(C=C4)Cl)F
    2.2 Other Identifiers
    2.2.1 UNII
    G7N11T8O78
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3r)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl Acetic Acid

    2. Mk-0524

    2.3.2 Depositor-Supplied Synonyms

    1. 571170-77-9

    2. Mk 0524

    3. Mk-0524

    4. Cardaptive

    5. Cordaptive

    6. Chembl426559

    7. G7n11t8o78

    8. 2-[(3r)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic Acid

    9. ((3r)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic Acid

    10. (-)-((3r)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic Acid

    11. 2-[(3r)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methanesulfonyl-1h,2h,3h,4h-cyclopenta[b]indol-3-yl]acetic Acid

    12. Cyclopent(b)indole-3-acetic Acid, 4-((4-chlorophenyl)methyl)-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3r)-

    13. Laropiprant [usan]

    14. Tedaptive

    15. Unii-g7n11t8o78

    16. Laropiprant [usan:inn:ban]

    17. Cyclopent[b]indole-3-acetic Acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3r)-

    18. [14c]-laropiprant

    19. Laropiprant [mi]

    20. Laropiprant [inn]

    21. Laropiprant (inn/usan)

    22. Laropiprant; Mk-0524

    23. Laropiprant (mk-0524)

    24. Laropiprant [mart.]

    25. Laropiprant [who-dd]

    26. Schembl991107

    27. Laropiprant [ema Epar]

    28. Amot0189

    29. Gtpl3356

    30. Dtxsid60205756

    31. Chebi:135942

    32. Bcpp000161

    33. Bcp02136

    34. Ex-a2099

    35. Zinc3961849

    36. Bdbm50205275

    37. Laropiprant,cas:571170-77-9

    38. Mk0524

    39. Akos030526850

    40. Am81247

    41. At34794

    42. Bcp9000944

    43. Cardaptive; Mk 0524; Mk-0524

    44. Cs-0539

    45. Db11629

    46. Ncgc00345790-10

    47. Ac-35835

    48. As-17012

    49. Hy-50175

    50. A25234

    51. D08940

    52. Q412291

    53. [(3r)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic Acid

    54. Laropiprant;(r)-2-(4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 435.9 g/mol
    Molecular Formula C21H19ClFNO4S
    XLogP33.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass435.0707351 g/mol
    Monoisotopic Mass435.0707351 g/mol
    Topological Polar Surface Area84.8 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity721
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1