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    Almotriptan

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 9,548Xls

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    2D Structure
    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 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

    2D Structure

    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.