Meptazinol: Difference between revisions

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{{Short description|Opioid analgesic drug}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462248630
| IUPAC_name = (''RS'')-3-(3-ethylEthyl-1-methylazepan-3-yl)phenol
| image = Meptazinol_racemate2DCSDMeptazinol.svg
| width = 300150
| chirality = [[Racemic mixture]]
| image2 =
| width2 =
| imagename = 1 : 1 mixture (racemate)
| drug_name = Meptazinol
 
<!--Clinical data-->
| tradename = Meptid
| Drugs.com = {{drugs.com|international|meptazinol}}
| licence_EU = <!-- EMEA requires brand name -->
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| bioavailability =
| protein_bound =
| metabolism = The peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours.
| elimination_half-life = Half-Lifelife (1.4–4 hours).
| excretion = The drug is rapidly metabolisedmetabolized to the [[glucuronide]], and mostly excreted in the urine.
 
<!--Identifiers-->
| index2_label = HCl
| CAS_number_Ref = {{cascite|changedcorrect|??CAS}}
| CAS_number = 54340-58-8
| UNII_RefCAS_number2_Ref = {{fdacitecascite|correct|FDACAS}}
| CAS_number2 = 59263-76-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 18Y7S5JKZD
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = T62FQ4ZCPA
| ATC_prefix = N02
| ATC_suffix = AX05
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 37469
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 18Y7S5JKZD
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08182
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<!--Chemical data-->
| chemical_formula =
| C=15 | H=23 | N=1 | O=1
| molecular_weight = 233.34922 g/mol
| smiles = OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
| InChI = 1/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
| InChIKey = JLICHNCFTLFZJN-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
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}}
 
'''Meptazinol''' (trade name '''Meptid''') is an [[opioid]] [[analgesic]] developed by [[Wyeth]] in the 1970s.<ref>{{ cite patent | country = US | status = patent | number = 4197239 | title = Hexahydroazepine, Piperidine and Pyrrolidine Derivatives | gdate = 1980-04-08 | inventor = Cavalla JF, Shepherd RG, White AC | assign1 = Wyeth }}</ref> Indications for use in moderate to severe [[pain]], most commonly used to treat pain in [[obstetrics]] ([[childbirth]]).

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

A partial [[mu opioid receptor|µμ-opioid receptor]] [[agonist]], its mixed [[agonist]]/[[Receptor antagonist|antagonist]] activity affords it a lower risk of [[physical dependence|dependence]] and [[drug abuse|abuse]] than full µμ [[agonist]]s like [[morphine]]. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other [[opioid]]s such as [[morphine]], [[pentazocine]], or [[buprenorphine]].<ref name="Holmes 1985">{{ cite journal | author vauthors= Holmes B, Ward A | title = Meptazinol. A Review of its Pharmacodynamic and Pharmacokinetic Properties and Therapeutic Efficacy | journal = Drugs | year = 1985 | volume = 30 | issue = 4 | pages = 285–312 | pmid = 2998723 | doi=10.2165/00003495-198530040-00001| s2cid = 208818234 }}</ref>
 
==References==
{{reflistReflist|30em}}
 
==External links==
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{{Analgesics}}
{{Opioidergics}}
 
[[Category:Synthetic opioids]]