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    Chemistry

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    Also known as: Butorphanol tartrate, 58786-99-5, Butorphanol (+)-tartrate salt, Stadol (tn), Butorphanol tartrate salt, Butorphanol tartrate (jan/usp)
    Molecular Formula
    C25H35NO8
    Molecular Weight
    477.5  g/mol
    InChI Key
    GMTYREVWZXJPLF-BTVKVFNOSA-N
    Butorphanol Tartrate
    A synthetic morphinan analgesic with narcotic antagonist action. It is used in the management of severe pain.
    1 2D Structure

    Butorphanol Tartrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol;(2R,3R)-2,3-dihydroxybutanedioic acid
    2.1.2 InChI
    InChI=1S/C21H29NO2.C4H6O6/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15;5-1(3(7)8)2(6)4(9)10/h6-7,13,15,19,23-24H,1-5,8-12,14H2;1-2,5-6H,(H,7,8)(H,9,10)/t19-,20+,21-;1-,2-/m11/s1
    2.1.3 InChI Key
    GMTYREVWZXJPLF-BTVKVFNOSA-N
    2.1.4 Canonical SMILES
    C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O.C(C(C(=O)O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 17-(cyclobutylmethyl)morphinan-3,14-diol

    2. Apo-butorphanol

    3. Bc 2627

    4. Bc-2627

    5. Bc2627

    6. Beforal

    7. Butorphanol

    8. Butorphanol Tartrate

    9. Dolorex

    10. Moradol

    11. Stadol

    12. Stadol Ns

    13. Torbugesic

    2.2.2 Depositor-Supplied Synonyms

    1. Butorphanol Tartrate

    2. 58786-99-5

    3. Butorphanol (+)-tartrate Salt

    4. Stadol (tn)

    5. Butorphanol Tartrate Salt

    6. Butorphanol Tartrate (jan/usp)

    7. Akos015994595

    8. Hs-0001

    9. Butorphanol (+)-tartrate Salt, >=99%

    10. D00837

    11. 786b995

    12. Butorphanol Tartrate, United States Pharmacopeia (usp) Reference Standard

    2.2.3 Other Synonyms

    1. Butorfanol

    2. Torate

    3. Torbutrol

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 477.5 g/mol
    Molecular Formula C25H35NO8
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count5
    Exact Mass477.23626707 g/mol
    Monoisotopic Mass477.23626707 g/mol
    Topological Polar Surface Area159 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity626
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    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 NameButorphanol tartrate
    Drug LabelButorphanol tartrate is a synthetically derived opioid agonist-antagonist analgesic of the phenanthrene series. The chemical name is (-)-17-(cyclobutylmethyl) morphinan-3, 14-diol [S-(R*,R*)] 2,3 dihydroxybutanedioate (1:1) (salt). The molecul...
    Active IngredientButorphanol tartrate
    Dosage FormInjectable; Spray, metered
    RouteNasal; Injection
    Strength2mg/ml; 1mg/ml; 1mg/spray
    Market StatusPrescription
    CompanyBedford; Hikma Farmaceutica; Novex; Mylan; Roxane

    2 of 2  
    Drug NameButorphanol tartrate
    Drug LabelButorphanol tartrate is a synthetically derived opioid agonist-antagonist analgesic of the phenanthrene series. The chemical name is (-)-17-(cyclobutylmethyl) morphinan-3, 14-diol [S-(R*,R*)] 2,3 dihydroxybutanedioate (1:1) (salt). The molecul...
    Active IngredientButorphanol tartrate
    Dosage FormInjectable; Spray, metered
    RouteNasal; Injection
    Strength2mg/ml; 1mg/ml; 1mg/spray
    Market StatusPrescription
    CompanyBedford; Hikma Farmaceutica; Novex; Mylan; Roxane

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antitussive Agents

    Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

    Narcotics

    Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

    Analgesics, Opioid

    Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

    Narcotic Antagonists

    Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Opioid Agonist/Antagonist [EPC]; Partial Opioid Agonists [MoA]; Competitive Opioid Antagonists [MoA]

    API Reference Price

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