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Chemistry

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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

LAROPIPRANT

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 Formula	C₂₁H₁₉ClFNO₄S
Molecular Weight	435.9 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	435.0707351 g/mol
Monoisotopic Mass	435.0707351 g/mol
Topological Polar Surface Area	84.8 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	721
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