Compound: nalbuphine
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@@H](O)CC[C@@]4(O)[C@H](N(CC6CCC6)CC5)C3
InChIKey: NETZHAKZCGBWSS-CEDHKZHLSA-N
Synonyms: nalbuphine, 20594-83-6, Nalbufina, Nalbuphinum, Intapan, L2T84IQI2K, N-Cyclobutylmethyl-4,5alpha-epoxy-3,6alpha,14-morphinantriol, DTXSID8023345, CHEBI:7454, DTXCID103345, 17-(Cyclobutylmethyl)-4,5alpha-epoxymorphinan-3,6alpha,14-triol, (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, Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, (5alpha,6alpha)-, (1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7,9,11(18)-triene-10,14,17-triol, (1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-triene-10,14,17-triol, (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, RefChem:57230, (1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo(9.6.1.01,13.05,17.07,18)octadeca-7,9,11(18)-triene-10,14,17-triol, 243-901-6, Nalbuphine (INN), CHEMBL895, 17-cyclobutylmethyl-4,5alpha-epoxymorphinan-3,6alpha,14-triol, NALBUPHINE [INN], Nalbuphine (1.0mg/ml in Acetonitrile), Intapan (TN), Nalbufina [DCIT], Nalbuphine [INN:BAN], Nalbuphinum [INN-Latin], UNII-L2T84IQI2K, NCGC00162275-02, EINECS 243-901-6, NALBUPHINE [MI], Prestwick0_000118, Prestwick1_000118, Prestwick2_000118, Prestwick3_000118, NALBUPHINE [VANDF], SCHEMBL3766, NALBUPHINE [WHO-DD], BSPBio_000136, BIDD:GT0060, SPBio_002075, BPBio1_000150, GTPL1663, SCHEMBL29389768, HMS2089I04, Tox21_112008, BDBM50105085, (5alpha,6alpha)-17-(cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol, DB00844, NCGC00179652-02, NCGC00179652-04, CAS-20594-83-6, NS00008318, C07251, D08246, EN300-19631168, Q277979, BRD-K66404838-003-03-8, BRD-K66404838-310-01-1, Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, 17-(Cyclobutylmethyl)-5alpha-4,5-epoxymorphinan-3,6alpha,14-triol, (-)-17-(cyclobutylmethyl)-4,5alpha-epoxymorphinan-3,6alpha,14-triol, 17-(CYCLOBUTYLMETHYL)-4,5.ALPHA.-EPOXYMORPHINAN-3,6.ALPHA.,14-TRIOL, (1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14,17-triol, Morphinan-3,6,14-triol, 17-(cyclobutylmethyl)-4,5-epoxy-, (5alpha,6alpha)- (9CI); Morphinan-3,6alpha,14-triol, 17-(cyclobutylmethyl)-4,5alpha-epoxy- (8CI); N-Cyclobutylmethyl-14-hydroxydihydronormorphine; Nalbuphine
Theoretical properties:
molecular_formula: C21H27NO4
molecular_weight: 357.4 g/mol
exact_mass: 357.19400834 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 26
topological_polar_surface_area: 73.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Nalbuphine is an organic heteropentacyclic compound. It has a role as an opioid analgesic and a mu-opioid receptor antagonist. It derives from a hydride of a morphinan.
chembl: NALBUPHINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.
Side effects of nalbuphine include sedation, sweatiness, clamminess, nausea, vomiting, dizziness, vertigo, dry mouth, and headache. Unlike other opioids, it has little to no capacity to cause euphoria or respiratory depression. There is also little to no incidence of dysphoria, dissociation, hallucinations, and related side effects at typical therapeutic doses. Nalbuphine is a mixed agonist/antagonist opioid modulator. Specifically, it acts as a moderate-efficacy partial agonist or antagonist of the μ-opioid receptor (MOR) and as a high-efficacy partial agonist of the κ-opioid receptor (KOR), whereas it has relatively low affinity for the δ-opioid receptor (DOR) and sigma receptors.
Nalbuphine was patented in 1968 and was introduced for medical use in the United States in 1979. It is marketed in many countries throughout the world.