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    Technical details about Dezocine, learn more about the structure, uses, toxicity, action, side effects and more

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    Dezocine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: Dalgan, 53648-55-8, Dezocina, Dezocinum, Docozine, Dozocine
    Molecular Formula
    C16H23NO
    Molecular Weight
    245.36  g/mol
    InChI Key
    VTMVHDZWSFQSQP-VBNZEHGJSA-N
    FDA UNII
    VHX8K5SV4X
    Dezocine is a partial opiate drug and is used for pain management. Dezocine is a very effective alternative to fentanyl when administered during outpatient laparoscopy, although is associated with an increased incidence of postoperative nausea.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,9S,15S)-15-amino-1-methyltricyclo[7.5.1.02,7]pentadeca-2(7),3,5-trien-4-ol
    2.1.2 InChI
    InChI=1S/C16H23NO/c1-16-8-4-2-3-5-12(15(16)17)9-11-6-7-13(18)10-14(11)16/h6-7,10,12,15,18H,2-5,8-9,17H2,1H3/t12-,15-,16+/m0/s1
    2.1.3 InChI Key
    VTMVHDZWSFQSQP-VBNZEHGJSA-N
    2.1.4 Canonical SMILES
    CC12CCCCCC(C1N)CC3=C2C=C(C=C3)O
    2.1.5 Isomeric SMILES
    C[C@]12CCCCC[C@H]([C@@H]1N)CC3=C2C=C(C=C3)O
    2.2 Other Identifiers
    2.2.1 UNII
    VHX8K5SV4X
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (-5alpha, 11alpha,13s)-13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecen-3-ol

    2. 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecenol

    3. 5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5alpha,11alpha,13s*)

    4. Dezocine Hydrobromide, (5alpha,11alpha,13*)-isomer

    5. Dezocine Hydrobromide, (5alpha,11alpha,13s*)-isomer

    6. Dezocine Hydrobromide, (5r-(5alpha,11alpha,13s*))-isomer

    7. Dezocine Hydrobromide, (5s-(5alpha,11alpha,13*))-isomer

    8. Dezocine, (5alpha,11alpha,13s*)-isomer

    9. Wy-16,225

    2.3.2 Depositor-Supplied Synonyms

    1. Dalgan

    2. 53648-55-8

    3. Dezocina

    4. Dezocinum

    5. Docozine

    6. Dozocine

    7. Dezocinum [inn-latin]

    8. Dezocina [inn-spanish]

    9. Wy-16225

    10. Vhx8k5sv4x

    11. Wy-16,225

    12. Chembl1685

    13. Chebi:4474

    14. Dezocine (usan)

    15. (-)-13beta-amino-5,6,7,8,9,10,11alpha,12-octahydro-5alpha-methyl-5,11-methanobenzocyclodecen-3-ol

    16. Dezocine [usan]

    17. (1r,9s,15s)-15-amino-1-methyltricyclo[7.5.1.02,7]pentadeca-2(7),3,5-trien-4-ol

    18. Dezocine [usan:inn]

    19. Unii-vhx8k5sv4x

    20. Dalgan (tn)

    21. Wy 16225

    22. Dezocine [inn]

    23. Dezocine [mi]

    24. Wy 16,225

    25. Dezocine [vandf]

    26. Dezocine [mart.]

    27. Dezocine [who-dd]

    28. Schembl3072

    29. Dezocine [orange Book]

    30. Dtxsid2022911

    31. (5r,11s,13s)-13-amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzo[10]annulen-3-ol

    32. Bdbm50276568

    33. Akos016014025

    34. Db01209

    35. C08010

    36. D00838

    37. Q1109018

    38. (1r,9s,15s)-15-amino-1-methyltricyclo[7.5.1.0^{2,7}]pentadeca-2,4,6-trien-4-ol

    39. 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecenol

    40. (-)-13.beta.-amino-5,6,7,8,9,10,11.alpha.,12-octahydro-5.alpha.-methyl-5,11-methanobenzocyclodecen-3-ol

    41. (5r,11s,13s)-13-amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzocyclodecen-3-ol

    42. 5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5.alpha.,11.alpha.,13s*)

    43. 5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5alpha,11alpha,13s*)-, (-)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 245.36 g/mol
    Molecular Formula C16H23NO
    XLogP33.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass245.177964357 g/mol
    Monoisotopic Mass245.177964357 g/mol
    Topological Polar Surface Area46.2 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity306
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated in the treatment of moderate to severe pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Dezocine is a parenteral narcotic analgesic possessing both agonist and antagonist activity. It is similar to morphine with respect to analgesic potency and onset and duration of action. The narcotic antagonist activity is greater than that of pentazocine.

    5.2 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.)

    5.3 ATC Code

    N - Nervous system

    N02 - Analgesics

    N02A - Opioids

    N02AX - Other opioids

    N02AX03 - Dezocine

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapid and complete following intramuscular administration.

    5.5 Metabolism/Metabolites

    Hepatic, via conjugation (glucuronidation).

    Dezocine has known human metabolites that include Dezocine glucuronide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    Elimination half-life following intramuscular administration averages 2.2 hours. Elimination half-life following a 5mg intravenous dose averages 1.7 to 2.6 hours (range 0.6 to 4.4 hours) while a 10mg dose averages 2.4 to 2.6 hours (range 1.2 to 7.4 hours). In patients with hepatic cirrhosis, the half-life is increased by 30 to 50%.

    5.7 Mechanism of Action

    Dezocine is a opioid analgesic drug of mixed agonist-antagonist type. It binds with stereospecific receptors at many sites within the central nervous system (CNS) to alter processes affecting both the perception of pain and the emotional response to pain. At least 2 of these types of receptors (mu and kappa) mediate analgesia. Mu receptors are widely distributed throughout the CNS, especially in the limbic system (frontal cortex, temporal cortex, amygdala, and hippocampus), thalamus, striatum, hypothalamus, and midbrain as well as laminae I, II, IV, and V of the dorsal horn in the spinal cord. Kappa receptors are localized primarily in the spinal cord and in the cerebral cortex.