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Eletriptan Hydrobromide

Synopsis, Chemistry

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Also known as: 177834-92-3, Eletriptan hbr, Relpax, Eletriptan hydrobromide [usan], Eletriptan (hydrobromide), (r)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole hydrobromide

Molecular Formula

C₂₂H₂₇BrN₂O₂S

Molecular Weight

463.4 g/mol

InChI Key

UTINOWOSWSPFLJ-FSRHSHDFSA-N

FDA UNII

M41W832TA3

Eletriptan Hydrobromide is a triptan with specific affinity for the 5-hydroxytriptamine1B/1D receptor. Eletriptan hydrobromide binds to and acts at serotonin 5-HT1B receptors located on intracranial blood vessels which leads to vasoconstriction. This drug may also exerts its effects by binding to and activating 5-HT 1D receptors on sensory nerve endings in the trigeminal system, which results in the inhibition of pro-inflammatory neuropeptide release. Eletriptan hydrobromide is used to relieve pain or symptoms associated with migraine headaches.

1 2D Structure

Eletriptan Hydrobromide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole;hydrobromide

2.1.2 InChI

InChI=1S/C22H26N2O2S.BrH/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20;/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3;1H/t19-;/m1./s1

2.1.3 InChI Key

UTINOWOSWSPFLJ-FSRHSHDFSA-N

2.1.4 Canonical SMILES

CN1CCCC1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br

2.1.5 Isomeric SMILES

CN1CCC[C@@H]1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br

2.2 Other Identifiers

2.2.1 UNII

M41W832TA3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole

2. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Monohydrobromide

3. 3-(1-methyl-2-pyrrolidinylmethyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Hydrobromide

4. Eletriptan

5. Relpax

6. Uk 166,044

7. Uk 166044

8. Uk-116,044-04

9. Uk-116044-04

10. Uk-166,044

11. Uk-166044

2.3.2 Depositor-Supplied Synonyms

1. 177834-92-3

2. Eletriptan Hbr

3. Relpax

4. Eletriptan Hydrobromide [usan]

5. Eletriptan (hydrobromide)

6. (r)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Hydrobromide

7. Eletriptan Monohydrobromide

8. Uk 116044-04

9. Chebi:61176

10. M41w832ta3

11. Uk-116,044-04

12. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Monohydrobromide

13. 5-[2-(benzenesulfonyl)ethyl]-3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indole;hydrobromide

14. Nsc-759258

15. 3-(((r)-1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)indole, Monohydrobromide

16. 5-[2-(phenylsulfonyl)ethyl]-3-[(2r)-pyrrolidin-2-ylmethyl]-1h-indole Hydrobromide

17. C22h26n2o2s.hbr

18. Unii-m41w832ta3

19. Relpax (tn)

20. Schembl317370

21. Chembl1201003

22. Dtxsid001016113

23. Hy-a0010

24. Eletriptan Hydrobromide (jan/usan)

25. Eletriptan Hydrobromide [mi]

26. Tox21_500408

27. Eletriptan Hydrobromide [jan]

28. Mfcd08141806

29. S3180

30. Akos024262728

31. Ac-3398

32. Bcp9000640

33. Ccg-221712

34. Cs-0379

35. Eletriptan Hydrobromide [mart.]

36. Nsc 759258

37. 3-[[(2r)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1h-indole Hydrobromide

38. Eletriptan Hydrobromide [usp-rs]

39. Eletriptan Hydrobromide [who-dd]

40. Ncgc00261093-01

41. Bs-42146

42. Eletriptan Hydrobromide, >=98% (hplc)

43. Eletriptan Hydrobromide [orange Book]

44. Sw220149-1

45. D01973

46. J-011323

47. J-520433

48. Q27130865

49. 3-(n-methyl-2(r)-pyrrolidinyl Methyl)-5-[2-(phenyl Sulfonyl)ethyl]-1h-indole Hydrobromide

50. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethly)-1h-indole Hydrobromide

51. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1h-indole Hydrobromide

52. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-[2-(phenyl Sulfonyl)ethyl]-1h-indole Hydrobromide

53. 3-{[1-methylpyrrolidin-2(r)-yl]methyl}-5-(2-phenylsulphonylethyl)-1h-indole Hydrobromide

54. (r)-3-[(1-methyl-2-pyrrolidinyl) Methyl]-5-[2-(phenylsulfonyl) Ethyl]-1h-indole Monohydrobromide

55. 1h-indole, 3-(((2r)-1-methyl-2-pyrrolidinyl))methyl)-5-(2-(phenylsulfonyl)ethyl)-, Monohydrobromide

56. 1h-indole, 3-[[(2r)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-, Hydrobromide (1:1)

57. 3-[[(2r)-1-methyl-2-pyrrolidinyl]me Thyl]-5-[2-(phenylsulfonyl)ethyl]-1h-indole Hydrobromide

58. 5-[2-(benzenesulfonyl)ethyl]-3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indol-1-ium;bromide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₇BrN₂O₂S
Molecular Weight	463.4 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	462.09766 g/mol
Monoisotopic Mass	462.09766 g/mol
Topological Polar Surface Area	61.6 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	582
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Eletriptan hydrobromide
Drug Label	RELPAX (eletriptan) Tablets contain eletriptan hydrobromide, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Eletriptan is chemically designated as (R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-...
Active Ingredient	Eletriptan hydrobromide
Dosage Form	Tablet
Route	oral
Strength	eq 40mg base; eq 20mg base; 40mg; 20mg
Market Status	Tentative Approval
Company	Apotex; Teva Pharms Usa

2 of 2
Drug Name	Eletriptan hydrobromide
Drug Label	RELPAX (eletriptan) Tablets contain eletriptan hydrobromide, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Eletriptan is chemically designated as (R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-...
Active Ingredient	Eletriptan hydrobromide
Dosage Form	Tablet
Route	oral
Strength	eq 40mg base; eq 20mg base; 40mg; 20mg
Market Status	Tentative Approval
Company	Apotex; Teva Pharms Usa

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Serotonin Receptor Agonists

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]