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Details

Stereochemistry RACEMIC
Molecular Formula C15H23NO
Molecular Weight 233.3492
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPTAZINOL

SMILES

CCC1(CCCCN(C)C1)C2=CC(O)=CC=C2

InChI

InChIKey=JLICHNCFTLFZJN-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C15H23NO
Molecular Weight 233.3492
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: http://www.shijiebiaopin.net/upload/product/201222217302623.PDF | https://www.drugs.com/uk/meptid-tablets-200mg-leaflet.html

Meptazinol is a unique opioid analgesic. Binding studies suggest a relative selectivity for mu-1 opioid receptor sites. Meptid is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic. The most commonly reported adverse reactions after treatment with meptazinol are nausea, vomiting, dizziness, diarrhoea and increased sweating, constipation, abdominal pain, rash, vertigo, headache, drowsiness, somnolence and dyspepsia.

CNS Activity

Originator

Wyeth
116
Curator's Comment: # Wyeth John & Brother Ltd.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Cholinesterase
14
Target ID: P81908
Gene ID: NA
Gene Symbol: BCHE
Target Organism: Equus caballus (Horse)
Inhibitor
8297
 3.6 µM [IC50]
Inhibitor
8297
 0.4 µM [IC50]
Partial Agonist
290
 8.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Meptid

Approved Use

The drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic.
Primary
Approved
8429
Meptid

Approved Use

The drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic.
Primary
Approved
8429
Meptid

Approved Use

The drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic.
PubMed

PubMed

TitleDatePubMed
Intramuscular on demand analgesia: double blind controlled trial of pethidine, buprenorphine, morphine, and meptazinol.
1983 Feb 26
Comparison of the cardiovascular effects of meptazinol and naloxone following haemorrhagic shock in rats and cats.
1985 Sep
Lack of sensitization during place conditioning in rats is consistent with the low abuse potential of tramadol.
2002 Aug 23
Inhibitory effect of intrathecal meptazinol on carrageenan-induced thermal hyperalgesia in rats.
2004 Feb 6
Antinociceptive effects of meptazinol and its isomers on carrageenan-induced thermal hyperalgesia in rats.
2004 Jun 25
Enhancement of systemic and CNS delivery of meptazinol hydrochloride by intranasal administration to rats.
2005 Aug
A novel method to calculate the extent and amount of drug transported into CSF after intranasal administration.
2005 Jan 31
Reflex activity caused by laryngoscopy and intubation is obtunded differently by meptazinol, nalbuphine and fentanyl.
2007 Jan
WITHDRAWN: Types of intra-muscular opioids for maternal pain relief in labour.
2007 Jul 18
Bis-(-)-nor-meptazinols as novel nanomolar cholinesterase inhibitors with high inhibitory potency on amyloid-beta aggregation.
2008 Apr 10
Prescribing intramuscular opioids for labour analgesia in consultant-led maternity units: a survey of UK practice.
2008 Jan
The crystal structure of a complex of acetylcholinesterase with a bis-(-)-nor-meptazinol derivative reveals disruption of the catalytic triad.
2009 Apr 23
Liquid chromatography/positive ion electrospray tandem mass spectrometry method for the quantification of hydrochloride meptazinol in human plasma: application to a pharmacokinetic study.
2009 Nov 15
In situ and in vivo study of nasal absorption of paeonol in rats.
2010
[Patient-controlled intravenous analgesia with remifentanil as an alternative to epidural analgesia during labor: case series and discussion of medicolegal aspects].
2010 Aug
Patents

Patents

JP2005520783A
40

Sample Use Guides

In Vivo Use Guide
Oral: One tablet (200 mg), with a glass of water, every four hours. Intramuscular: 75-100mg. The injection may be repeated 2-4 hourly as required. For obstetric pain a dose of 100-150mg should be used according to weight. This dose should approximate 2mg/kg. Intravenous: 50-100mg by slow intravenous injection. The injection may be repeated 2-4 hourly as required. If vomiting occurs, a suitable antiemetic should be given.
Route of Administration: Other
In Vitro Use Guide
Approximately 20 to 40% of 3H-opiate binding is inhibited by meptazinol at concentrations less than 5 nM, whereas the inhibition for D-[3H]Ala2-D-Leu5-enkaphalin usually ranges from 15 to 20%.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:05:06 GMT 2023
Edited
by admin
on Sat Dec 16 16:05:06 GMT 2023
Record UNII
18Y7S5JKZD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPTAZINOL
INN   MI   WHO-DD  
INN  
Official Name English
MEPTAZINOL [MI]
Common Name English
PHENOL, 3-(3-ETHYLHEXAHYDRO-1-METHYL-1H-AZEPIN-3-YL)-
Systematic Name English
Meptazinol [WHO-DD]
Common Name English
IL-22811
Code English
M-(3-ETHYLHEXAHYDRO-1-METHYL-1H-AZEPIN-3-YL)PHENOL
Systematic Name English
meptazinol [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QN02AX05
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
WHO-ATC N02AX05
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
LIVERTOX 602
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
NCI_THESAURUS C67413
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
Code System Code Type Description
CAS
54340-58-8
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
WIKIPEDIA
MEPTAZINOL
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
DRUG CENTRAL
1706
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
EVMPD
SUB08761MIG
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID6048543
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
DRUG BANK
DB13478
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
MERCK INDEX
m7200
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY Merck Index
SMS_ID
100000081482
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
MESH
D008621
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL314437
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
INN
3605
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
NCI_THESAURUS
C87360
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
ECHA (EC/EINECS)
259-109-9
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
RXCUI
6761
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY RxNorm
FDA UNII
18Y7S5JKZD
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
PUBCHEM
41049
Created by admin on Sat Dec 16 16:05:07 GMT 2023 , Edited by admin on Sat Dec 16 16:05:07 GMT 2023
PRIMARY
Related Record Type Details
Structure of MEPTAZINOL, (R)-
ENANTIOMER -> RACEMATE
Structure of MEPTAZINOL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of MEPTAZINOL, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of MEPTAZINOL
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