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    2D Structure
    Also known as: Buprenorphine hydrochloride, Ncgc00247733-01, Dsstox_cid_28831, Dsstox_rid_83100, Dsstox_gsid_48905, Tox21_112899
    Molecular Formula
    C29H42ClNO4
    Molecular Weight
    504.1  g/mol
    InChI Key
    UAIXRPCCYXNJMQ-CHLZSUIASA-N
    A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2S,6R,14R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol;hydrochloride
    2.1.2 InChI
    InChI=1S/C29H41NO4.ClH/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28;/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3;1H/t20-,21-,24-,26+,27-,28+,29?;/m1./s1
    2.1.3 InChI Key
    UAIXRPCCYXNJMQ-CHLZSUIASA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O.Cl
    2.1.5 Isomeric SMILES
    C[C@]([C@H]1C[C@@]23CCC1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O.Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 6029 M

    2. 6029-m

    3. 6029m

    4. Buprenex

    5. Buprenorphine

    6. Buprenorphine Hydrochloride

    7. Buprex

    8. Hydrochloride, Buprenorphine

    9. Prefin

    10. Rx 6029 M

    11. Rx-6029-m

    12. Rx6029m

    13. Subutex

    14. Temgsic

    15. Temgesic

    2.2.2 Depositor-Supplied Synonyms

    1. Buprenorphine Hydrochloride

    2. Ncgc00247733-01

    3. Dsstox_cid_28831

    4. Dsstox_rid_83100

    5. Dsstox_gsid_48905

    6. Tox21_112899

    7. Cas-53152-21-9

    2.3 Create Date
    2006-12-27
    3 Chemical and Physical Properties
    Molecular Weight 504.1 g/mol
    Molecular Formula C29H42ClNO4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass503.2802365 g/mol
    Monoisotopic Mass503.2802365 g/mol
    Topological Polar Surface Area62.2 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity869
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count1
    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 NameBuprenorphine hydrochloride
    Drug LabelBuprenorphine hydrochloride sublingual tablets contains buprenorphine HCl.Buprenorphine is a partial agonist at the mu-opioid receptor and an antagonist at the kappa-opioid receptor. Buprenorphine is a Schedule III narcotic under the Controlled Subst...
    Active IngredientBuprenorphine hydrochloride
    Dosage FormInjectable; Tablet
    RouteSublingual; Injection
    Strengtheq 2mg base; eq 0.3mg base/ml; eq 8mg base
    Market StatusPrescription
    CompanyHospira; Ethypharm; Luitpold; Eurohlth Intl; Roxane; Barr

    2 of 2  
    Drug NameBuprenorphine hydrochloride
    Drug LabelBuprenorphine hydrochloride sublingual tablets contains buprenorphine HCl.Buprenorphine is a partial agonist at the mu-opioid receptor and an antagonist at the kappa-opioid receptor. Buprenorphine is a Schedule III narcotic under the Controlled Subst...
    Active IngredientBuprenorphine hydrochloride
    Dosage FormInjectable; Tablet
    RouteSublingual; Injection
    Strengtheq 2mg base; eq 0.3mg base/ml; eq 8mg base
    Market StatusPrescription
    CompanyHospira; Ethypharm; Luitpold; Eurohlth Intl; Roxane; Barr

    4.2 Drug Indication

    Sixmo is indicated for substitution treatment for opioid dependence in clinically stable adult patients who require no more than 8 mg/day of sublingual buprenorphine, within a framework of medical, social and psychological treatment.

    Treatment of opioid dependence

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    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.)

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Partial Opioid Agonists [MoA]; Partial Opioid Agonist [EPC]
    5.3 ATC Code

    N07BC01