MEQUITAMIUM IODIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H25N2S.I
Molecular Weight	464.406
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[I-].C[N+]12CCC(CC1)C(CN3C4=C(SC5=C3C=CC=C5)C=CC=C4)C2

InChI

InChIKey=SWVANDLDSRKJFI-UHFFFAOYSA-M

InChI=1S/C21H25N2S.HI/c1-23-12-10-16(11-13-23)17(15-23)14-22-18-6-2-4-8-20(18)24-21-9-5-3-7-19(21)22;/h2-9,16-17H,10-15H2,1H3;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	HI
Molecular Weight	127.91241
Charge	0
Count

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

Molecular Formula	C21H25N2S
Molecular Weight	337.502
Charge	1
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2226618 | https://www.ncbi.nlm.nih.gov/pubmed/8068497 | https://www.ncbi.nlm.nih.gov/pubmed/1611232 | https://www.ncbi.nlm.nih.gov/pubmed/9522168 | https://adisinsight.springer.com/drugs/800000086

Mequitamium iodide (LG 30435) is a quaternary ammonium phenothiazine. Mequitamium iodide was found to bind with high affinity only to histamine H1 receptors and to muscarinic acetylcholine receptors. The (+)-(S)-enantiomer is 10-fold more potent than (-)-(R)-enantiomer as a histamine antagonist, while the two enantiomers show the same antimuscarinic activity in vitro. In animal models, it exerts antiasthmatic and antiallergic properties. It was being clinically investigated as a treatment of asthma and rhinitis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Antihistaminic and antiallergic properties of dextro-mequitamium iodide in upper and lower guinea pig airways: comparison with azelastine.	1998-04	9522168
Absolute configuration and biological activity of mequitamium iodide enantiomers.	1994	8068497
Effect of mequitamium iodide (LG 30435) on airway microvascular leakage in the guinea-pig.	1992-06	1611232
High-affinity binding of mequitamium iodide (LG 30435) to muscarinic and histamine H1 receptors.	1990-07-17	2226618

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:43:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:43:14 GMT 2025`
Record UNII	50D69ZKZ7M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEQUITAMIUM IODIDE

Official Name

English

mequitamium iodide [INN]

Preferred Name

English

(±)-1-METHYL-3-(PHENOTHIAZIN-10-YLMETHYL)QUINUCLIDINIUM IODIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578