Meptazinol

Meptazinol (trade name Meptid) is an opioid analgesic developed by Wyeth in the 1970s.[1] Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth).

Meptazinol
Clinical data
Trade namesMeptid
AHFS/Drugs.comInternational Drug Names
Dependence
liability		Low
Routes of
administration		Oral, IM, IV
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
MetabolismThe peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours
Elimination half-lifeHalf-life (1.4–4 hours)
ExcretionThe drug is rapidly metabolized to the glucuronide, and mostly excreted in the urine
Identifiers
IUPAC name
  • (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.718
Chemical and physical data
FormulaC15H23NO
Molar mass233.355 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
InChI
  • InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3 Y
  • Key:JLICHNCFTLFZJN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Meptazinol is a 3-phenylazepane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes.

A partial μ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full μ agonists like morphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine.[2]

References
  1. US patent 4197239, Cavalla JF, Shepherd RG, White AC, "Hexahydroazepine, Piperidine and Pyrrolidine Derivatives", issued 1980-04-08, assigned to Wyeth
  2. Holmes B, Ward A (1985). "Meptazinol. A Review of its Pharmacodynamic and Pharmacokinetic Properties and Therapeutic Efficacy". Drugs. 30 (4): 285–312. doi:10.2165/00003495-198530040-00001. PMID 2998723. S2CID 208818234.
  • Meptazinol at the US National Library of Medicine Medical Subject Headings (MeSH)


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