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{{Drugbox
{{Drugbox
| IUPAC_name       = 3-(3-ethyl-1-methylazepan-3-yl)phenol
| Verifiedfields = changed
| image             = Meptazinol.png
| Watchedfields = changed
| width             = 200
| verifiedrevid = 462248630
| image2           =  
| IUPAC_name = (''RS'')-3-(3-ethyl-1-methylazepan-3-yl)phenol
| width2           =  
| image = Meptazinol.png
| imagename         = <!-- else may use drug_name -->
| width = 300
| drug_name         = Meptazinol
| image2 =
| CAS_number        = 54340-58-8
| width2 =
| CAS_supplemental  =
| imagename = 1 : 1 mixture (racemate)
| ATC_prefix        = N02
| drug_name = Meptazinol
| ATC_suffix        = AX04
 
| ATC_supplemental =
<!--Clinical data-->
| PubChem          = 41049
| tradename =   
| DrugBank          =
| Drugs.com = {{drugs.com|international|meptazinol}}
| chemical_formula  =  
| licence_EU = <!-- EMEA requires brand name -->
| C=15 | H=23 | N=1 |O=1
| licence_US = <!-- FDA may use generic name -->
| molecular_weight  = 233.34922 g/mol
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| smiles            = CCC1(CCCCN(C1)C)C2=CC(=CC=C2)O
| pregnancy_US = <!-- A / B / C / D / X -->
| synonyms          = Meptid
| pregnancy_category =   
| density          =
| legal_AU = Schedule 4
| melting_point    =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| melting_high      =
| legal_UK = POM
| melting_notes    =
| legal_US = <!-- OTC / Rx-only  / Schedule I, II, III, IV, V -->
| boiling_point    =
| legal_status =
| boiling_notes    =
| solubility        =
| specific_rotation =
| sec_combustion    =
| bioavailability  =
| protein_bound    =
| metabolism        =
| elimination_half-life =
| excretion        =
| licence_EU       = <!-- EMEA requires brand name -->  
| licence_US       = <!-- FDA may use generic name -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US     = <!-- A / B / C / D / X -->
| pregnancy_category=   
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK         = POM
| legal_US         = <!-- OTC / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status     =  
| dependency_liability = Low
| dependency_liability = Low
| routes_of_administration = Oral, [[intramuscular|IM]], [[intravenous|IV]]
| routes_of_administration = Oral, [[intramuscular|IM]], [[intravenous|IV]]
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = The peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours.
| elimination_half-life = Half-Life (1.4–4 hours).
| excretion = The drug is rapidly metabolised to the glucuronide, and mostly excreted in the urine.
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 59263-76-2
| ATC_prefix = N02
| ATC_suffix = AX05
| ATC_supplemental = 
| PubChem = 41049
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 37469
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 18Y7S5JKZD
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08182
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 314437
<!--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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JLICHNCFTLFZJN-UHFFFAOYSA-N
| synonyms = 
| density = 
| melting_notes = 
| boiling_point = 
| solubility = 
| specific_rotation = 
| sec_combustion = 
}}
}}
__NOTOC__


'''Meptazinol''' ('''Meptid<sup>®</sup>''') is an [[opioid]] [[analgesic]] for use with moderate to severe [[pain]], most commonly used to treat pain in [[obstetrics]] ([[childbirth]]). A partial [[mu opioid receptor|µ-opioid receptor]] [[agonist]], its mixed [[agonist]]/[[antagonist]] activity affords it a lower risk of [[physical dependence|dependence]] and [[drug abuse|abuse]] than full µ [[agonist]]s like [[morphine]]. Meptazinol exhibits 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">Holmes B, Ward A. "Meptazinol. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy." ''Drugs''. 1985 Oct; 30(4):285-312. PMID 2998723</ref>
{{SI}}


==References==
{{CMG}}
{{reflist|2}}
 
==Overview==
'''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]]). A partial [[mu opioid receptor|µ-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 µ [[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 = 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}}</ref>


==External links==
It does not appear in the US Controlled Substances Act 1970; it may or may not be regulated as an analogue of controlled relatives such as [[proheptazine]] (ACSCN 9643)
* {{MeshName|Meptazinol}}


{{Opioids}}
==References==
{{Reflist|2}}


{{pharma-stub}}
{{Analgesics}}
{{Opioidergics}}


[[Category:Opioids]]
[[Category:Synthetic opioids]]
[[Category:Pain]]
[[Category:Azepanes]]
[[Category:Drugs]]
[[Category:Phenols]]
{{WikiDoc Sources}}
[[Category:Drug]]

Revision as of 14:51, 13 April 2015

Meptazinol
Clinical data
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 metabolised to the glucuronide, and mostly excreted in the urine.
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC15H23NO
Molar mass233.34922 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)


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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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). 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]

It does not appear in the US Controlled Substances Act 1970; it may or may not be regulated as an analogue of controlled relatives such as proheptazine (ACSCN 9643)

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.
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