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Also known as: 154323-57-6, Axert, Almogran, Las-31416, Las 31416, N,n-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)methyl)-1h-indol-3-yl)ethanamine
Molecular Formula
C17H25N3O2S
Molecular Weight
335.5  g/mol
InChI Key
WKEMJKQOLOHJLZ-UHFFFAOYSA-N
FDA UNII
1O4XL5SN61

Almotriptan
Almotriptan is a sulfonamide triptan with extracerebral, intracranial vasoconstrictor activity. Almotriptan selectively binds to and activates serotonin 5-HT 1B and 1D receptors in the central nervous system (CNS), thereby causing extracerebral, intracranial 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.
Almotriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of almotriptan is as a Serotonin 1b Receptor Agonist, and Serotonin 1d Receptor Agonist.
1 2D Structure

Almotriptan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine
2.1.2 InChI
InChI=1S/C17H25N3O2S/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/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3
2.1.3 InChI Key
WKEMJKQOLOHJLZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)CS(=O)(=O)N3CCCC3
2.2 Other Identifiers
2.2.1 UNII
1O4XL5SN61
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Almogran

2. Almotriptan Malate

3. Axert

2.3.2 Depositor-Supplied Synonyms

1. 154323-57-6

2. Axert

3. Almogran

4. Las-31416

5. Las 31416

6. N,n-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)methyl)-1h-indol-3-yl)ethanamine

7. Almotriptan (usan)

8. 1-(((3-(2-(dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine

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

10. Nsc-760092

11. Pyrrolidine, 1-(((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)sulfonyl)-

12. 1o4xl5sn61

13. Chebi:520985

14. N,n-dimethyl-2-{5-[(pyrrolidin-1-ylsulfonyl)methyl]-1h-indol-3-yl}ethanamine

15. Ncgc00095135-01

16. Almotriptan [usan]

17. Pyrrolidine, 1-[[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]sulfonyl]-

18. Dsstox_cid_24289

19. Dsstox_rid_80142

20. Dsstox_gsid_44289

21. Almotrintan

22. Almotriptan [usan:inn:ban]

23. Dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1h-indol-3-yl}ethyl)amine

24. Unii-1o4xl5sn61

25. Cas-154323-57-6

26. Sr-05000001986

27. Pnu-180638

28. Spectrum_001884

29. Almotriptan [mi]

30. Las 31416almotriptan

31. Spectrum2_000498

32. Spectrum3_001006

33. Spectrum4_001134

34. Spectrum5_001554

35. Almotriptan [inn]

36. Almotriptan [vandf]

37. Schembl1957

38. Chembl1505

39. Almotriptan [who-dd]

40. Bspbio_002731

41. Kbiogr_001647

42. Kbioss_002414

43. Bidd:gt0048

44. Spectrum1505204

45. Spbio_000395

46. Gtpl7110

47. Dtxsid5044289

48. Hy-b0383a

49. Kbio2_002408

50. Kbio2_004976

51. Kbio2_007544

52. Kbio3_001951

53. Zinc18087

54. Hms1922l13

55. Pharmakon1600-01505204

56. Bcp06539

57. Tox21 111444

58. Tox21_111444

59. Ccg-39569

60. Nsc760092

61. Akos015895080

62. Tox21_111444_1

63. Ac-8799

64. Am84500

65. Cs-4530

66. Db00918

67. Nsc 760092

68. Sb19515

69. Ncgc00095135-02

70. Ncgc00095135-03

71. Ncgc00095135-04

72. Ncgc00095135-05

73. Ws-02332

74. Db-064033

75. Ft-0651595

76. 23a576

77. D02824

78. D86136

79. Ab01563047_01

80. Ab01563047_02

81. A809522

82. L000846

83. Q409729

84. Sr-05000001986-1

85. Brd-k67601717-001-02-0

86. 1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine

87. N,n-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)-methyl)-1h-indol-3-yl)ethanamine

88. N,n-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1h- Indol-3-yl]-ethanamine

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 335.5 g/mol
Molecular Formula C17H25N3O2S
XLogP31.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass335.16674822 g/mol
Monoisotopic Mass335.16674822 g/mol
Topological Polar Surface Area64.8 Ų
Heavy Atom Count23
Formal Charge0
Complexity483
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAxert
PubMed HealthAlmotriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAXERT (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 IngredientAlmotriptan malate
Dosage FormTablet
RouteOral
Strengtheq 6.25mg base; eq 12.5mg base
Market StatusPrescription
CompanyJanssen Pharms

2 of 2  
Drug NameAxert
PubMed HealthAlmotriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAXERT (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 IngredientAlmotriptan malate
Dosage FormTablet
RouteOral
Strengtheq 6.25mg base; eq 12.5mg base
Market StatusPrescription
CompanyJanssen Pharms

4.2 Drug Indication

For the treatment of acute migraine headache in adults


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Almotriptan is a selective 5-hydroxytryptamine receptor subtype agonist indicated for the acute treatment of migraine attacks with or without aura in adults. Almotriptan is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. Almotriptan is an agonist for a vascular 5-hydroxytryptamine receptor subtype (probably a member of the 5-HT1D family) having only a weak affinity for 5-HT1A, 5-HT5A, and 5-HT7 receptors and no significant affinity or pharmacological activity at 5-HT2, 5-HT3 or 5-HT4 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Almotriptan also activates 5-HT1 receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Almotriptan in humans.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ALMOTRIPTAN
5.3.2 FDA UNII
1O4XL5SN61
5.3.3 Pharmacological Classes
Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]
5.4 ATC Code

N02CC05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N02 - Analgesics

N02C - Antimigraine preparations

N02CC - Selective serotonin (5ht1) agonists

N02CC05 - Almotriptan


5.5 Absorption, Distribution and Excretion

Route of Elimination

Almotriptan is eliminated primarily by renal excretion (about 75% of the oral dose), with approximately 40% of an administered dose excreted unchanged in urine. Approximately 13% of the administered dose is excreted via feces, both unchanged and metabolized.


Volume of Distribution

180 to 200 L


Clearance

57 L/h [healthy]

34.2 L/h [moderate renal impairment (creatinine clearance between 31 and 71 mL/min)]

9.8 L/h [severe renal impairment (creatinine clearance between 10 and 30 mL/min)]


5.6 Metabolism/Metabolites

Almotriptan has known human metabolites that include 2-hydroxy-almotriptan and methyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

3-4 hours


5.8 Mechanism of Action

Almotriptan binds with high affinity to human 5-HT1B and 5-HT1D receptors leading to cranial blood vessel constriction.


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08-Jan-2021
27-Sep-2024
KGS
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