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Meptazinol

April 05, 2024

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
  • (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol
CAS Number
  • 54340-58-8 Y
  • HCl: 59263-76-2 Y
PubChem CID
  • 41049
ChemSpider
  • 37469 Y
UNII
  • 18Y7S5JKZD
  • HCl: T62FQ4ZCPA Y
KEGG
  • D08182 Y
ChEMBL
  • ChEMBL314437 Y
CompTox Dashboard (EPA)
  • DTXSID6048543
ECHA InfoCard100.053.718
Chemical and physical data
FormulaC15H23NO
Molar mass233.355 g·mol−1
3D model (JSmol)
  • Interactive image
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 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 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.

External links edit


 

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

April 05, 2024
meptazinol, trade, name, meptid, opioid, analgesic, developed, wyeth, 1970s, indications, moderate, severe, pain, most, commonly, used, treat, pain, obstetrics, childbirth, clinical, datatrade, namesmeptidahfs, drugs, cominternational, drug, namesdependencelia. 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 MeptazinolClinical dataTrade namesMeptidAHFS Drugs comInternational Drug NamesDependenceliabilityLowRoutes ofadministrationOral IM IVATC codeN02AX05 WHO Legal statusLegal statusAU S4 Prescription only UK POM Prescription only Pharmacokinetic dataMetabolismThe peak analgesic effect is seen within 30 60 minutes and lasts about 3 4 hoursElimination half lifeHalf life 1 4 4 hours ExcretionThe drug is rapidly metabolized to the glucuronide and mostly excreted in the urineIdentifiersIUPAC name RS 3 3 Ethyl 1 methylazepan 3 yl phenolCAS Number54340 58 8 YHCl 59263 76 2 YPubChem CID41049ChemSpider37469 YUNII18Y7S5JKZDHCl T62FQ4ZCPA YKEGGD08182 YChEMBLChEMBL314437 YCompTox Dashboard EPA DTXSID6048543ECHA InfoCard100 053 718Chemical and physical dataFormulaC 15H 23N OMolar mass233 355 g mol 13D model JSmol Interactive imageChiralityRacemic mixtureSMILES OC1 CC CC C2 CCCCN C2 C CC C1InChI 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 YKey JLICHNCFTLFZJN UHFFFAOYSA N Y N Y what is this verify Meptazinol is a 3 phenylazepane derivative whereas the other phenazepanes like ethoheptazine and proheptazine are 4 phenylazepanes A partial m opioid receptor agonist its mixed agonist antagonist activity affords it a lower risk of dependence and abuse than full m 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 edit US patent 4197239 Cavalla JF Shepherd RG White AC Hexahydroazepine Piperidine and Pyrrolidine Derivatives issued 1980 04 08 assigned to Wyeth 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 External links editMeptazinol at the U S National Library of Medicine Medical Subject Headings MeSH nbsp This analgesic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Meptazinol amp oldid 1181417715, wikipedia, wiki, book, books, library,

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