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Meptazinol

From Wikipedia, the free encyclopedia
Opioid analgesic drug
Pharmaceutical compound
Meptazinol
Clinical data
Trade namesMeptid
AHFS/Drugs.comInternational Drug Names
Dependence
liability
Low
Routes of
administration
By mouth,intramuscular,intravenous
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismThe peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours
Eliminationhalf-lifeHalf-life (1.4–4 hours)
ExcretionThe drug is rapidly metabolized to theglucuronide, and mostly excreted in the urine
Identifiers
  • (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.053.718Edit this at Wikidata
Chemical and physical data
FormulaC15H23NO
Molar mass233.355 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
  • 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 checkY
  • Key:JLICHNCFTLFZJN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Meptazinol, sold under the brand nameMeptid, is anopioidanalgesic developed byWyeth in the 1970s.[1] Indications for use in moderate to severepain, most commonly used to treat pain inobstetrics (childbirth).

Meptazinol is a 3-phenylazepane derivative, whereas the other phenazepanes likeethoheptazine andproheptazine are4-phenylazepanes.

A partialμ-opioid receptoragonist, its mixedagonist/antagonist activity affords it a lower risk ofdependence andabuse than full μagonists likemorphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to otheropioids such asmorphine,pentazocine, orbuprenorphine.[2]

References

[edit]
  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.

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