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Almotriptan Malate

Synopsis, Chemistry

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TABLET;ORAL - EQ 12.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - EQ 6.25MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

TABLET;ORAL - EQ 12.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - EQ 6.25MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 181183-52-8, Almotriptan maleate, Axert, Las 31416 d,l-malate acid, Almotriptan (malate), Almogran

Molecular Formula

C₂₁H₃₁N₃O₇S

Molecular Weight

469.6 g/mol

InChI Key

QHATUKWEVNMHRY-UHFFFAOYSA-N

FDA UNII

PJP312605E

Almotriptan Malate is the malate salt of almotriptan, a sulfonamide triptan with vasoconstrictor activity. Almotriptan selectively binds to and activates serotonin 5-HT 1B and 1D receptors in the central nervous system (CNS), thereby causing cerebral blood vessel constriction. This may lead to pain relief from vascular headaches. Almotriptan may also relieve vascular headaches by preventing the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater during a migraine, by reducing extravasation of plasma proteins, and by decreasing the release of other mediators of inflammation from the trigeminal nerve.

1 2D Structure

Almotriptan Malate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine;2-hydroxybutanedioic acid

2.1.2 InChI

InChI=1S/C17H25N3O2S.C4H6O5/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20;5-2(4(8)9)1-3(6)7/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3;2,5H,1H2,(H,6,7)(H,8,9)

2.1.3 InChI Key

QHATUKWEVNMHRY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCC1=CNC2=C1C=C(C=C2)CS(=O)(=O)N3CCCC3.C(C(C(=O)O)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

PJP312605E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Almogran

2. Almotriptan

3. Axert

2.3.2 Depositor-Supplied Synonyms

1. 181183-52-8

2. Almotriptan Maleate

3. Axert

4. Las 31416 D,l-malate Acid

5. Almotriptan (malate)

6. Almogran

7. Pnu-180638e

8. Almotriptan Malate [usan]

9. Almotriptan D,l-hydrogenmalate

10. Chebi:53781

11. Las-31416 D,l-malate Acid

12. Pjp312605e

13. 181183-52-8(almotriptan Malate)

14. Las-31416-d,l-malate-acid

15. N,n-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)methyl)-1h-indol-3-yl)ethan-1-amine 2-hydroxysuccinate

16. 1-(((3-(2-(dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine Malate (1:1)

17. 1-(((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)sulfonyl)pyrrolidine, Hydroxybutanedioate (1:1)

18. N,n-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1h-indol-3-yl]ethanamine;2-hydroxybutanedioic Acid

19. Pnu 180638e

20. Unii-pjp312605e

21. Sr-05000001986

22. Axert (tn)

23. Almotriptan Malate (usp)

24. 1-[[[2-(dimethyl-amino)ethyl]-1h-indol-5-yl]methyl]sulfonyl]pyrrolidine Malate

25. Almotriptan Malate (axert)

26. 1-(((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)sulfonyl)pyrrolidine, Hydroxybutanedionate (1:1)

27. Mls006010048

28. Schembl221131

29. Almotriptan Maleate [mi]

30. Chembl1200521

31. Dtxsid1044225

32. Almotriptan Malate [vandf]

33. Almotriptan Malate(pnu180638)

34. Hms3651a12

35. Hms3884p05

36. Almotriptan Malate [mart.]

37. Almotriptan Malate [usp-rs]

38. Almotriptan Malate [who-dd]

39. Bcp05632

40. Hy-b0383

41. Mfcd08067740

42. Pnu180638

43. S2096

44. (zznon-labelled)almotriptan-d6 Malate

45. Akos015950790

46. Bcp9000276

47. Ccg-269445

48. Pnu 180638

49. Almotriptan Malate [orange Book]

50. Almotriptan Malate [ep Monograph]

51. Almotriptan Malate [usp Monograph]

52. As-12142

53. Butanedioic Acid, Hydroxy-, Compd. With 1-(((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)sulfonyl)pyrrolidine (1:1)

54. Smr004701216

55. Ft-0661519

56. Sw219418-1

57. D02825

58. F14758

59. J-011571

60. Sr-05000001986-2

61. Q27124206

62. 1-(((3-(2-(dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine Malate

63. 3-[2-(dimethylamino)ethyl]-5-(pyrrolidin-1-ylsulfonylmethyl )-1h-indole Malate

64. 1-(((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)sulfonyl)pyrrolidine Hydroxybutanedioate

65. Butanedioic Acid, 2-hydroxy-, Compd. With N,n-dimethyl-5-[(1-pyrrolidinylsulfonyl)methyl]-1h-indole-3-ethanamine (1:1)

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₁N₃O₇S
Molecular Weight	469.6 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	9
Exact Mass	469.18827151 g/mol
Monoisotopic Mass	469.18827151 g/mol
Topological Polar Surface Area	160 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	612
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
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	Almotriptan malate
Drug Label	AXERT (almotriptan malate) Tablets contain almotriptan malate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist. Almotriptan malate is chemically designated as 1-[[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidi...
Active Ingredient	Almotriptan malate
Dosage Form	Tablet
Route	oral
Strength	6.25mg; 12.5mg
Market Status	Tentative Approval
Company	Teva Pharms

2 of 2
Drug Name	Almotriptan malate
Drug Label	AXERT (almotriptan malate) Tablets contain almotriptan malate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist. Almotriptan malate is chemically designated as 1-[[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidi...
Active Ingredient	Almotriptan malate
Dosage Form	Tablet
Route	oral
Strength	6.25mg; 12.5mg
Market Status	Tentative Approval
Company	Teva Pharms

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]