MEPTAZINOL

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 Search

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
Sources: http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1435297377639.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cholinesterase 14 Target ID: P81908 Gene ID: NA Gene Symbol: BCHE Target Organism: Equus caballus (Horse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3607358	Inhibitor 8297	3.6 µM [IC50]
Acetylcholinesterase 207 Target ID: CHEMBL3198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3607358	Inhibitor 8297	0.4 µM [IC50]
Mu opioid receptor 221 Target ID: CHEMBL2858 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6319856 \| https://www.ncbi.nlm.nih.gov/pubmed/6141283 \| https://www.ncbi.nlm.nih.gov/pubmed/3001685	Partial Agonist 290	8.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Obstetric pain 2 Sources: https://www.medicines.org.uk/emc/medicine/21242	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.
Postoperative pain 22 Sources: https://www.medicines.org.uk/emc/medicine/21242	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.
Pain of renal colic 2 Sources: https://www.medicines.org.uk/emc/medicine/21242	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

Title	Date	PubMed
Intramuscular on demand analgesia: double blind controlled trial of pethidine, buprenorphine, morphine, and meptazinol.	1983 Feb 26	6402201
Comparison of the cardiovascular effects of meptazinol and naloxone following haemorrhagic shock in rats and cats.	1985 Sep	4052729
Lack of sensitization during place conditioning in rats is consistent with the low abuse potential of tramadol.	2002 Aug 23	12161254
Enhancement of systemic and CNS delivery of meptazinol hydrochloride by intranasal administration to rats.	2005 Aug	16268513
A novel method to calculate the extent and amount of drug transported into CSF after intranasal administration.	2005 Jan 31	15652208
Structural comparisons of meptazinol with opioid analgesics.	2005 Mar	15715930
Synthesis and relative bioavailability of meptazinol benzoyl esters as prodrugs.	2005 May 16	15863326
Pharmacokinetic behavior in plasma, cerebrospinal fluid and cerebral cortex after intranasal administration of hydrochloride meptazinol.	2005 Sep 30	15993428
Investigation of the binding mode of (-)-meptazinol and bis-meptazinol derivatives on acetylcholinesterase using a molecular docking method.	2006 Mar	16404617
Conformational re-analysis of (+)-meptazinol: an opioid with mixed analgesic pharmacophores.	2006 Sep	16923347
WITHDRAWN: Types of intra-muscular opioids for maternal pain relief in labour.	2007 Jul 18	17636658
Bis-(-)-nor-meptazinols as novel nanomolar cholinesterase inhibitors with high inhibitory potency on amyloid-beta aggregation.	2008 Apr 10	18333606
(3S,4S)-3-Ethyl-4-hydr-oxy-3-(3-methoxy-phen-yl)-1-methyl-azepan-1-ium d-tartrate dihydrate.	2008 Apr 2	21202277
Prescribing intramuscular opioids for labour analgesia in consultant-led maternity units: a survey of UK practice.	2008 Jan	17981457
1-Methyl-3-(3-oxocyclo-hex-1-en-yl)azepan-2-one.	2008 Sep 13	21201143
The crystal structure of a complex of acetylcholinesterase with a bis-(-)-nor-meptazinol derivative reveals disruption of the catalytic triad.	2009 Apr 23	19326912
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	19819764
In situ and in vivo study of nasal absorption of paeonol in rats.	2010	21614179
[Patient-controlled intravenous analgesia with remifentanil as an alternative to epidural analgesia during labor: case series and discussion of medicolegal aspects].	2010 Aug	20806149

Patents

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 UTC 2023` Edited by `admin` on `Sat Dec 16 16:05:06 UTC 2023`
Record UNII	18Y7S5JKZD
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MEPTAZINOL

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