MEPTAZINOL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H23NO.ClH
Molecular Weight	269.81
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MPJUSISYVXABBH-UHFFFAOYSA-N

InChI=1S/C15H23NO.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Structural comparisons of meptazinol with opioid analgesics.	2005 Mar	15715930
Design, synthesis, and bioavailability evaluation of coumarin-based prodrug of meptazinol.	2005 Nov 15	16154745
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
(3S,4S)-3-Ethyl-4-hydr-oxy-3-(3-methoxy-phen-yl)-1-methyl-azepan-1-ium d-tartrate dihydrate.	2008 Apr 2	21202277
1-Methyl-3-(3-oxocyclo-hex-1-en-yl)azepan-2-one.	2008 Sep 13	21201143

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 07:32:49 UTC 2023` Edited by `admin` on `Sat Dec 16 07:32:49 UTC 2023`
Record UNII	T62FQ4ZCPA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEPTAZINOL HYDROCHLORIDE

Official Name

English

MEPTAZINOL HYDROCHLORIDE [USAN]

Common Name

English

WY 22811 HCL

Code

English

MEPTID

Brand Name

English

PHENOL, 3-(3-ETHYLHEXAHYDRO-1-METHYL-1H-AZEPIN-3-YL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

MEPTAZINOL HCL

Common Name

English

WY-22811 HYDROCHLORIDE

Code

English

IL-22811 HYDROCHLORIDE

Code

English

IL-22811 HCL

Code

English

MEPTAZINOL HYDROCHLORIDE [MI]

Common Name

English

MEPTAZINOL HYDROCHLORIDE [MART.]

Common Name

English

MEPTAZINOL HYDROCHLORIDE (±)-

Common Name

English

IL 22811 HCL

Code

English

WY-22811

Code

English

Meptazinol hydrochloride [WHO-DD]

Common Name

English

WY-22811 HCL

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67413