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Nalbuphine Hydrochloride
Also known as: Nubain, Nalbuphine hcl, 23277-43-2, Nalbuphine hydrochloride [usan], En-2234a, Nalbufine hydrochloride
Molecular Formula
C21H28ClNO4
Molecular Weight
393.9  g/mol
InChI Key
YZLZPSJXMWGIFH-BCXQGASESA-N
FDA UNII
ZU4275277R

A narcotic used as a pain medication. It appears to be an agonist at KAPPA RECEPTORS and an antagonist or partial agonist at MU RECEPTORS.
1 2D Structure

Nalbuphine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R,4aS,7S,7aR,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol;hydrochloride
2.1.2 InChI
InChI=1S/C21H27NO4.ClH/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12;/h4-5,12,15-16,19,23-25H,1-3,6-11H2;1H/t15-,16+,19-,20-,21+;/m0./s1
2.1.3 InChI Key
YZLZPSJXMWGIFH-BCXQGASESA-N
2.1.4 Canonical SMILES
C1CC(C1)CN2CCC34C5C(CCC3(C2CC6=C4C(=C(C=C6)O)O5)O)O.Cl
2.1.5 Isomeric SMILES
C1CC(C1)CN2CC[C@]34[C@@H]5[C@H](CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O)O.Cl
2.2 Other Identifiers
2.2.1 UNII
ZU4275277R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. En 2234a

2. En-2234a

3. En2234a

4. Nalbuphine

5. Nalbuphine Serb

6. Nubain

2.3.2 Depositor-Supplied Synonyms

1. Nubain

2. Nalbuphine Hcl

3. 23277-43-2

4. Nalbuphine Hydrochloride [usan]

5. En-2234a

6. Nalbufine Hydrochloride

7. Nsc-757829

8. Zu4275277r

9. (4r,4as,7s,7ar,12bs)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol;hydrochloride

10. Nalbuphine Hydrochloride (usan)

11. Chebi:7455

12. Nalbufina Clorhidrato [spanish]

13. En 2234a

14. Einecs 245-549-9

15. Nalbuphinehydrochloride

16. Unii-zu4275277r

17. Prestwick_344

18. Nubain (tn)

19. 17-(cyclobutylmethyl)-4,5alpha-epoxymorphinan-3,6alpha,14-triol Hydrochloride

20. (5alpha,6alpha)-17-(cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol Hydrochloride

21. Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, Hydrochloride, (5-alpha,6-alpha)-

22. Schembl41123

23. Mls002154202

24. Chembl1201132

25. Dtxsid20177844

26. Hms1568g18

27. Nalbuphine Hydrochloride [mi]

28. Ccg-220118

29. Nsc 757829

30. Pw-4142

31. Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, Hydrochloride, (5alpha,6alpha)-

32. Morphinan-3,6-alpha,14-triol, 17-(cyclobutylmethyl)-4,5-alpha-epoxy-, Hydrochloride

33. Nalbuphine Hydrochloride [mart.]

34. Nalbuphine Hydrochloride [vandf]

35. Nalbuphine Hydrochloride [who-dd]

36. Bn161328

37. Smr001233488

38. Nalbuphine Hydrochloride [orange Book]

39. D00843

40. E98629

41. Q27107499

42. (-)-17-(cyclobutylmethyl)- 4,5a-epoxymorphinan- 3,6a,14-triol Hydrochloride

43. 17-(cyclobutylmethyl)-4,5.alpha.-epoxymorphinan-3,6.alpha.,14-triol Hydrochloride

44. Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, Hydrochloride, (5.alpha.,6.alpha.)-

45. Nalbuphine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 393.9 g/mol
Molecular Formula C21H28ClNO4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass393.1706861 g/mol
Monoisotopic Mass393.1706861 g/mol
Topological Polar Surface Area73.2 Ų
Heavy Atom Count27
Formal Charge0
Complexity597
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 NameNalbuphine hydrochloride
Drug LabelAmpulFliptop VialProtect from light.Rx OnlyNalbuphine hydrochloride is a synthetic opioid agonist-antagonist analgesic of the phenanthrene series. It is chemically related to both the widely used opioid antagonist, naloxone, and the potent opioid ana...
Active IngredientNalbuphine hydrochloride
Dosage FormInjectable
RouteInjection
Strength20mg/ml; 10mg/ml
Market StatusPrescription
CompanyHospira

2 of 2  
Drug NameNalbuphine hydrochloride
Drug LabelAmpulFliptop VialProtect from light.Rx OnlyNalbuphine hydrochloride is a synthetic opioid agonist-antagonist analgesic of the phenanthrene series. It is chemically related to both the widely used opioid antagonist, naloxone, and the potent opioid ana...
Active IngredientNalbuphine hydrochloride
Dosage FormInjectable
RouteInjection
Strength20mg/ml; 10mg/ml
Market StatusPrescription
CompanyHospira

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.)


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