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Basic information
- CAS
23277-43-2- Standard SMILES
Cl.Oc1ccc2c3c1O[C@H]1[C@@H](O)CC[C@@]4(O)[C@@H](C2)N(CC2CCC2)CC[C@]314- InChIKey
YZLZPSJXMWGIFH-BCXQGASESA-N- Molecular formula
- C21H28ClNO4
- Average molar mass
- 393.9 g/mol
- Monoisotopic mass
- 393.17068606
Overview
Nalbuphine Hydrochloride is the hydrochloride salt form of nalbuphine, a synthetic phenanthrene opioid with opiate agonist and antagonist effects, used to treat moderate to severe pain and provide preoperative and postoperative analgesia and sedation. Nalbuphine hydrochloride binds to kappa-, mu- and delta-opioid receptors but not to sigma-opioid receptors. This opioid exerts its analgesic actions primarily through kappa-opioid-receptor agonism and partially through mu-opioid receptor agonism.
Names & identifiers
- Preferred name
- Nalbuphine Hydrochloride
- IUPAC
- (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
Names & synonyms
NALBUPHINE HYDROCHLORIDE23277-43-2Nalbuphine HCLEN-2234ANalbufine hydrochlorideEn 2234ANalbufina clorhidratoNSC-757829ZU4275277RDTXSID20177844(5alpha,6alpha)-17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol hydrochlorideN-Cyclobutylmethyl-14-hydroxydihydronormorphine hydrochloride
Show more names
CHEBI:7455NALBUPHINE HCIRefChem:57231DTXCID80100335EN2234A245-549-917-cyclobutylmethyl-4,5alpha-epoxymorphinan-3,6alpha,14-triol hydrochlorideNubain
Database identifiers
- CAS
23277-43-2- PubChem CID
- 5360733
- DTXSID
DTXSID20177844- ChEMBL
CHEMBL1201132- UNII
- ZU4275277R
- EC Number
- 245-549-9
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 73.2 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 597
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section180.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (63.9%): Fatal if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P320, P321, P330, P333+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 61 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 19-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20141
Hazard Classes and CategoriesAcute Tox. 2 (63.9%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Nalbuphine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
NALBUPHINE HCI
Competitive Opioid Antagonists [MoA]; Partial Opioid Agonists [MoA]; Opioid Agonist/Antagonist [EPC]
NALBUPHINE HYDROCHLORIDE
Opioid Agonist/Antagonist [EPC]; Partial Opioid Agonists [MoA]; Competitive Opioid Antagonists [MoA]
MeSH Pharmacological ClassificationCompounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Related reactions
1 records
Compound notes
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