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    Also known as: Ergotamine tartrate, Ergotamine bitartrate, 379-79-3, Schembl8045, Akos015897172, Ac-14836
    Molecular Formula
    C37H41N5O11
    Molecular Weight
    731.7  g/mol
    InChI Key
    NMTWKEWYQXZGCI-DDLCCZDQSA-N
    Ergotamine Tartrate
    A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.
    1 2D Structure

    Ergotamine Tartrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;2,3-dihydroxybutanedioic acid
    2.1.2 InChI
    InChI=1S/C33H35N5O5.C4H6O6/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32;5-1(3(7)8)2(6)4(9)10/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39);1-2,5-6H,(H,7,8)(H,9,10)/t21-,25-,26+,27+,32-,33+;/m1./s1
    2.1.3 InChI Key
    NMTWKEWYQXZGCI-DDLCCZDQSA-N
    2.1.4 Canonical SMILES
    CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C.C(C(C(=O)O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C.C(C(C(=O)O)O)(C(=O)O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Cornutamine

    2. Ergo Kranit

    3. Ergo Sanol

    4. Ergo-kranit

    5. Ergodryl Mono

    6. Ergomar

    7. Ergostat

    8. Ergotamine

    9. Ergotamine Tartrate

    10. Ergotamine Tartrate (2:1)

    11. Ergotaminine

    12. Gynergen

    13. Lingraine

    14. Mono, Ergodryl

    15. Tartrate, Ergotamine

    2.2.2 Depositor-Supplied Synonyms

    1. Ergotamine Tartrate

    2. Ergotamine Bitartrate

    3. 379-79-3

    4. Schembl8045

    5. Akos015897172

    6. Ac-14836

    2.3 Create Date
    2007-05-07
    3 Chemical and Physical Properties
    Molecular Weight 731.7 g/mol
    Molecular Formula C37H41N5O11
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count7
    Exact Mass731.28025714 g/mol
    Monoisotopic Mass731.28025714 g/mol
    Topological Polar Surface Area233 Ų
    Heavy Atom Count53
    Formal Charge0
    Complexity1350
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count2
    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 NameErgomar
    PubMed HealthErgotamine Tartrate (By mouth)
    Drug ClassesAntimigraine
    Active IngredientErgotamine tartrate
    Dosage FormTablet
    RouteSublingual
    Strength2mg
    Market StatusPrescription
    CompanyRosedale Therapeutic

    2 of 2  
    Drug NameErgomar
    PubMed HealthErgotamine Tartrate (By mouth)
    Drug ClassesAntimigraine
    Active IngredientErgotamine tartrate
    Dosage FormTablet
    RouteSublingual
    Strength2mg
    Market StatusPrescription
    CompanyRosedale Therapeutic

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Adrenergic alpha-1 Receptor Agonists

    Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Agonists.)

    Analgesics, Non-Narcotic

    A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)

    Oxytocics

    Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157) (See all compounds classified as Oxytocics.)

    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.)

    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
    Ergotamines [CS]; Ergotamine Derivative [EPC]

    API Reference Price

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    DOSAGE - TABLET;ORAL - 100MG;1MG

    USFDA APPLICATION NUMBER - 84294

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    USFDA APPLICATION NUMBER - 86557

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