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Dezocine

Synopsis, Chemistry

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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

Dezocine

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 Formula	C₁₆H₂₃NO
Molecular Weight	245.36 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	245.177964357 g/mol
Monoisotopic Mass	245.177964357 g/mol
Topological Polar Surface Area	46.2 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	306
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.