Diprenorphine

Synopsis, Chemistry

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Also known as: 14357-78-9, Diprenorfin, Revivon, Dea no. 9058, 1f0l5n25zz, Chebi:4650

Molecular Formula

C₂₆H₃₅NO₄

Molecular Weight

425.6 g/mol

InChI Key

OIJXLIIMXHRJJH-KNLIIKEYSA-N

FDA UNII

1F0L5N25ZZ

A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.

1 2D Structure

Diprenorphine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxypropan-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

2.1.2 InChI

InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1

2.1.3 InChI Key

OIJXLIIMXHRJJH-KNLIIKEYSA-N

2.1.4 Canonical SMILES

CC(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

2.1.5 Isomeric SMILES

CC(C)([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

2.2 Other Identifiers

2.2.1 UNII

1F0L5N25ZZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diprenorphine Hydrochloride

2. Hydrochloride, Diprenorphine

3. Revivon

2.3.2 Depositor-Supplied Synonyms

1. 14357-78-9

2. Diprenorfin

3. Revivon

4. Dea No. 9058

5. 1f0l5n25zz

6. Chebi:4650

7. Chembl281786

8. M. 5050

9. Diprenorphine (inn)

10. M50-50 Injection

11. M5050

12. Diprenorphine [inn:ban]

13. Diprenorphine [inn]

14. M-5050

15. Diprenorfina [inn-spanish]

16. (1s,2s,6r,14r,15r,16r)-5-(cyclopropylmethyl)-16-(2-hydroxypropan-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

17. Diprenorfina

18. Diprenorphinum

19. 21-cyclopropyl-6,7,8,14-tetrahydro-7alpha-(1-hydroxy-1-methylethyl)-6,14-endo-ethanooripavine

20. Diprenorphinum [inn-latin]

21. Unii-1f0l5n25zz

22. (5?,7?)-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-?,?-dimethyl-6,14-ethenomorphinan-7-methanol

23. Einecs 238-325-7

24. M 5050 Injection

25. Diprenorphine-hcl

26. Diprenorphine [mi]

27. M50-50

28. Schembl164910

29. Gtpl1617

30. Dtxsid00903941

31. Zinc4102215

32. Bdbm50001714

33. Akos024457358

34. Db01548

35. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-.alpha.,.alpha.-dimethyl-, (5.alpha.,7.alpha.)-

36. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)-

37. Hy-107742

38. D07863

39. M 5050

40. Q424009

41. Epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)-

42. (5alpha,7alpha)-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-6,14-ethenomorphinan-7-methanol

43. 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-?,?-dimethyl-6,14-ethenomorphinan-7-methanol

44. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(1s,2r,6s,14r,15r,16r)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-2-propanol

45. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(1s,2r,6s,14r,15r,16r)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-2-propanol(diprenorphine)

46. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7(12),8,10-trien-16-yl]-2-propanol

47. 6,14-endo-ethanotetrahydrooripavine, 21-cyclopropyl-7a-(1-hydroxy-1-methylethyl)- (8ci) 1-n-cyclopropylmethyl-6,7,8,14-tetrahydro-6,14-endoethano-7-(2'-hydroxy-2'-propyl)nororipavine

48. 6,14-ethenomorphinan-3-ol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-18-(1-hydroxy-1-methylethyl)-6-methoxy-, (5alpha,6beta,14beta,18r)-

49. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)- (9ci)

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₅NO₄
Molecular Weight	425.6 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	425.25660860 g/mol
Monoisotopic Mass	425.25660860 g/mol
Topological Polar Surface Area	62.2 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	783
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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

Diprenorphine is indicated to reverse the effects of powerful opioids including etorphine and carfentanil, often used for tranquilizing large animals. This drug is not approved for use in humans.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Narcotic Antagonists

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

5.2 Mechanism of Action

Diprenorphine binds approximately equally to the three subtypes of opioid receptorsand antagonizes them.