(1S,5R,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

• ChemBase ID: 722
• Molecular Formular: C21H27NO4
• Molecular Mass: 357.44338
• Monoisotopic Mass: 357.19400835
• SMILES: O1C2[C@]34[C@](O)([C@H](N(CC3)CC3CCC3)Cc3c4c1c(O)cc3)CC[C@@H]2O
• Canonical SMILES: O[C@H]1CC[C@@]2([C@@]34C1Oc1c4c(C[C@H]2N(CC3)CC2CCC2)ccc1O)O
• InChI: InChI=1S/C21H27NO4/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/t15-,16+,19?,20-,21+/m0/s1
• InChIKey: NETZHAKZCGBWSS-XDWDPSITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,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
• IUPAC Traditional name: nalbuphine
• Brand Name: Nalbufina [DCIT]; Nalbuphine HCL; Nalbuphinum [INN-Latin]; Nubain
• Synonyms: Nalbuphine

Database IDs

• CAS Number: 20594-83-6
• PubChem SID: 160964185
• PubChem CID: 5360630

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.392419
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.743254
• LogD (pH = 7.4): -0.7291438
• Log P: 1.1929245
• Molar Refractivity: 96.9999 cm^3
• Polarizability: 38.206367 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.0
• LOG S: -2.23
• Solubility (Water): 2.09e+00 g/l

PROPERTIES

Physical Property

• Solubility: 35.5 mg/mL at 25 oC as HCl salt
• Hydrophobicity(logP): 1.4

DETAILS

DrugBank - DB00844

• Drug Groups: approved
• Description: A narcotic used as a pain medication. It appears to be an agonist at kappa opioid receptors and an antagonist or partial agonist at mu opioid receptors. [PubChem]
• Indication: For the relief of moderate to severe pain.
• Pharmacology: Nalbuphine is a synthetic opioid agonist-antagonist analgesic of the phenanthrene series. Nalbuphine's analgesic potency is essentially equivalent to that of morphine on a milligram basis. The opioid antagonist activity of nalbuphine is one-fourth as potent as nalorphine and 10 times that of pentazocine. Nalbuphine by itself has potent opioid antagonist activity at doses equal to or lower than its analgesic dose. When administered following or concurrent with mu agonist opioid analgesics (e.g., morphine, oxymorphone, fentanyl), nalbuphine may partially reverse or block opioid-induced respiratory depression from the mu agonist analgesic. Nalbuphine may precipitate withdrawal in patients dependent on opioid drugs. Nalbuphine should be used with caution in patients who have been receiving mu opioid analgesics on a regular basis.
• Toxicity: Oral, acute LD50 is 1100 mg/kg in dog. Symptoms of overdose include primarily sleepiness and mild dysphoria.
• Affected Organisms: Humans and other mammals
• Absorption: The mean absolute bioavailability was 81% and 83% for the 10 and 20 mg intramuscular doses, respectively, and 79% and 76% following 10 and 20 mg of subcutaneous nalbuphine.
• Half Life: The plasma half-life of nalbuphine is 5 hours, and in clinical studies the duration of analgesic activity has been reported to range from 3 to 6 hours.
• Protein Binding: Not appreciably bound.
• References: Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. Pubmed