Nalbuphine

Not to be confused with Nalorphine.
Nalbuphine
Skeletal formula
Ball-and-stick model of nalbuphine
Clinical data
Trade namesNubain, Nalpain, Nalbuphin, others
Other namesEN-2234A; N-Cyclobutylmethyl-14-hydroxydihydronormorphine; 17-Cyclobutylmethyl-4,5α-epoxymorphinan-3,6α,14-triol; N-Cyclobutylmethyl-4,5α-epoxy-3,6α,14-morphinantriol
AHFS/Drugs.comMonograph
MedlinePlusa682668
Pregnancy
category
  • B
Routes of
administration		Intravenous, intramuscular, subcutaneous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class A2 (Narcotic drugs)[1]
  • CA: Schedule IV
  • US: Rx only (unscheduled) Schedule IV in some states
  • Federally Uncontrolled (RX-only), except in KY, C-IV
Pharmacokinetic data
Bioavailability• Oral: 11% (young adults), >44% (elderly)[2]
• IMTooltip Intramuscular injection: 81% (10 mg), 83% (20 mg)
• SCTooltip Subcutaneous injection: 76% (20 mg), 79% (10 mg)[3]
Protein binding50%[2]
MetabolismLiver (glucuronidation)[5][2]
MetabolitesGlucuronide conjugates (inactive), others[4][5][2]
Onset of action• Oral: <1 hour[2]
• Rectal: <30 minutes[2]
• IVTooltip Intravenous injection: 2–3 minutes[6]
• IMTooltip Intramuscular injection: <15 minutes[6]
• SCTooltip Subcutaneous injection: <15 minutes[6]
Elimination half-life~5 hours (3–6 hours)<[4]
Duration of action3–6 hours[6]
ExcretionUrine, bile, feces;[2] 93% within 6 hours[7]
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.039.895 Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO4
Molar mass357.450 g·mol−1
3D model (JSmol)
  • O[C@@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@@]3(O)CC4)CC6CCC6
  • 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 checkY
  • Key:NETZHAKZCGBWSS-CEDHKZHLSA-N checkY
  (verify)

Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain.[4][8][6] It is given by injection into a vein, muscle, or fat.[4][6]

Side effects of nalbuphine include sedation, sweatiness, clamminess, nausea, vomiting, dizziness, vertigo, dry mouth, and headache.[8] Unlike other opioids, it has little to no capacity to cause euphoria or respiratory depression.[4][8] There is also little to no incidence of dysphoria, dissociation, hallucinations, and related side effects at typical therapeutic doses.[4][8] Nalbuphine is a mixed agonist/antagonist opioid modulator.[4][8] 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.[9][8]

Nalbuphine was patented in 1963[10] and was introduced for medical use in the United States in 1979.[11][12] It is marketed in many countries throughout the world.[13]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
  2. ^ a b c d e f g Bissonnette B (14 May 2014). Pediatric Anesthesia. PMPH-USA. pp. 398–. ISBN 978-1-60795-213-8.
  3. ^ Excerpta medica. Section 24: Anesthesiology. 1988. 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.
  4. ^ a b c d e f g Narver HL (March 2015). "Nalbuphine, a non-controlled opioid analgesic, and its potential use in research mice". Lab Animal. 44 (3): 106–110. doi:10.1038/laban.701. PMID 25693108. S2CID 25378355.
  5. ^ a b Waldman SD (9 June 2011). Pain Management E-Book. Elsevier Health Sciences. pp. 910–. ISBN 978-1-4377-3603-8.
  6. ^ a b c d e f Smith HS, Pappagallo M (6 September 2012). Essential Pain Pharmacology: The Prescriber's Guide. Cambridge University Press. pp. 343–. ISBN 978-0-521-75910-6.
  7. ^ Yoo YC, Chung HS, Kim IS, Jin WT, Kim MK (Mar–Apr 1995). "Determination of nalbuphine in drug abusers' urine". Journal of Analytical Toxicology. 19 (2): 120–123. doi:10.1093/jat/19.2.120. PMID 7769781.
  8. ^ a b c d e f Schmidt WK, Tam SW, Shotzberger GS, Smith DH, Clark R, Vernier VG (February 1985). "Nalbuphine". Drug and Alcohol Dependence. 14 (3–4): 339–362. doi:10.1016/0376-8716(85)90066-3. PMID 2986929.
  9. ^ Cite error: The named reference PengKnapp2007 was invoked but never defined (see the help page).
  10. ^ US Patent 3393197 - Nusubstituted-14-hydroxydihydronormorphines
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 528. ISBN 9783527607495.
  12. ^ Cite error: The named reference Malamed2009 was invoked but never defined (see the help page).
  13. ^ "Nalbuphine".