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    Chemistry

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    Also known as: 143388-64-1, Naratriptan hcl, Amerge, Naramig, Gr-85548a, Gr 85548a
    Molecular Formula
    C17H26ClN3O2S
    Molecular Weight
    371.9  g/mol
    InChI Key
    AWEZYKMQFAUBTD-UHFFFAOYSA-N
    FDA UNII
    10X8X4P12Z
    Naratriptan Hydrochloride
    Naratriptan Hydrochloride is the hydrochloride salt form of naratriptan, a sulfonamide with selective serotonin (5-HT) 1 receptor agonistic activity and anti-migraine property. Naratriptan hydrochloride binds selectively and with high affinity to the 5-HT1D and 5-HT1B receptor subtypes. Activation of these 5-HT1D/B receptors located on intracranial blood vessels leads to vasoconstriction and provides relief of migraine headaches. Naratriptan hydrochloride may also exerts its effect by stimulation of 5-HT1D/1B receptors on sensory nerve endings in the trigeminal system thereby decreasing the release of pro-inflammatory neuropeptides.
    1 2D Structure

    Naratriptan Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
    2.1.3 InChI Key
    AWEZYKMQFAUBTD-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    10X8X4P12Z
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, Monohydrochloride

    2. Amerge

    3. Colatan

    4. Gr 85548a

    5. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulfonamide

    6. N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide Monohydrochloride

    7. Naramig

    8. Naratriptan

    2.3.2 Depositor-Supplied Synonyms

    1. 143388-64-1

    2. Naratriptan Hcl

    3. Amerge

    4. Naramig

    5. Gr-85548a

    6. Gr 85548a

    7. Naratriptan (hydrochloride)

    8. Gr-85548a Hydrochloride

    9. N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide Monohydrochloride

    10. 10x8x4p12z

    11. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, Monohydrochloride

    12. Dsstox_cid_28990

    13. Dsstox_rid_83255

    14. N-methyl-2-(3-(1-methylpiperidin-4-yl)-1h-indol-5-yl)ethanesulfonamide Hydrochloride

    15. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide;hydrochloride

    16. Dsstox_gsid_49064

    17. Chebi:7479

    18. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

    19. Cas-143388-64-1

    20. Naratriptan Hydrochloride [usan]

    21. Ncgc00181786-01

    22. Unii-10x8x4p12z

    23. Amerge Hydrochloride

    24. Amerge (tn)

    25. Mfcd08141821

    26. Naratriptan Hydrochloride [usan:usp]

    27. N-methyl-2-[3-(1-methyl-4-piperidyl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

    28. Schembl41527

    29. Mls006010726

    30. Chembl1200601

    31. Dtxsid6049064

    32. Hy-b0197a

    33. Amy41021

    34. Bcp04270

    35. Tox21_113617

    36. Tox21_500466

    37. Gg-548

    38. Naratriptan Hydrochloride (jan/usp)

    39. Rb3224

    40. S1488

    41. Naratriptan Hydrochloride [mi]

    42. Akos005145806

    43. Tox21_113617_1

    44. Ac-5014

    45. Ccg-221770

    46. Naratriptan Hydrochloride [jan]

    47. Naratriptan Hydrochloride [mart.]

    48. Naratriptan Hydrochloride [vandf]

    49. Ncgc00181786-02

    50. Ncgc00261151-01

    51. As-58417

    52. Naratriptan Hydrochloride [usp-rs]

    53. Naratriptan Hydrochloride [who-dd]

    54. Smr002529694

    55. Naratriptan Hydrochloride, >=98% (hplc)

    56. Ft-0672649

    57. Sw219416-1

    58. D00674

    59. Naratriptan Hydrochloride [orange Book]

    60. Naratriptan Hydrochloride [usp Monograph]

    61. 388n641

    62. A808063

    63. J-007804

    64. Q-201448

    65. Q27107505

    66. N-methyl-2-[3-(1-methyl-4-piperidinyl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

    67. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethane-1-sulfonamide Hydrochloride

    68. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulphonamide Hydrochloride

    69. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulphonamide, Hydrochloride

    70. Naratriptan Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    71. 2-[3-(1-methyl-piperidin-4-yl)-1h-indol-5-yl]-ethanesulfonic Acid Methylamide Hydrochloride

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 371.9 g/mol
    Molecular Formula C17H26ClN3O2S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass371.1434259 g/mol
    Monoisotopic Mass371.1434259 g/mol
    Topological Polar Surface Area73.6 Ų
    Heavy Atom Count24
    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 Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAmerge
    PubMed HealthNaratriptan (By mouth)
    Drug ClassesAntimigraine
    Drug LabelAMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
    Active IngredientNaratriptan hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 2.5mg base; eq 1mg base
    Market StatusPrescription
    CompanyGlaxosmithkline

    2 of 2  
    Drug NameAmerge
    PubMed HealthNaratriptan (By mouth)
    Drug ClassesAntimigraine
    Drug LabelAMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
    Active IngredientNaratriptan hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 2.5mg base; eq 1mg base
    Market StatusPrescription
    CompanyGlaxosmithkline

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Serotonin 5-HT1 Receptor Agonists

    Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)

    Vasoconstrictor Agents

    Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

    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]

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    04-Mar-2021
    19-Sep-2024
    KGS
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    DOSAGE - TABLET;ORAL - EQ 1MG BASE **Federal ...DOSAGE - TABLET;ORAL - EQ 1MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20763

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    DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20763

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