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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22N2S
Molecular Weight 322.4689
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEQUITAZINE

SMILES

c1ccc2c(c1)N(C[C@]3([H])CN4CCC3CC4)c5ccccc5S2

InChI

InChIKey=HOKDBMAJZXIPGC-INIZCTEOSA-N
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H22N2S
Molecular Weight 322.4689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Levomequitazine is the L-enantiomer of mequitazine. The antihistaminergic activity mainly resides in the S-enantiomer, L-mequitazine, whereas the anticholinergic activity mainly resides in the D-enantiomer. It was shown, that L-enantiomer of mequitazine is less potent antagonist of human M3 muscarinic acetylcholine receptors than D-enantiomer. In vitro binding studies have shown that the affinity of L-mequitazine for H1 receptors is approximately ten times higher and to muscarinic receptors ten times lower, compared to d-mequitazine. Memory impairment was observed after administration of L-mequitazine 10 mg alone on delayed recall. This could be due to indirect effects of H1 receptor blockade. L-mequitazine 10 mg produced mild driving impairment, whereas L-mequitazine 2.5 and 5.0 mg show no effects on driving. Levomequitazine had been in phase III clinical trials by Pierre Fabre for the treatment of perennial allergic rhinitis and seasonal allergic rhinitis.

Approval Year

PubMed

PubMed

TitleDatePubMed
Characterization of V0162, a new long-acting antagonist at human M3 muscarinic acetylcholine receptors.
2015 Oct
On-the-road driving performance after use of the antihistamines mequitazine and l-mequitazine, alone and with alcohol.
2016 Sep

Sample Use Guides

Single doses of 2.5, 5.0 and 10 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:45:49 UTC 2021
Edited
by admin
on Sat Jun 26 11:45:49 UTC 2021
Record UNII
5G2MWA892Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEQUITAZINE
INN  
INN  
Official Name English
L-MEQUITAZINE
Common Name English
(S)-MEQUITAZINE
Common Name English
LEVOMEQUITAZINE [INN]
Common Name English
10-(((3S)-1-AZABICYCLO(2.2.2)OCTAN-3-YL)METHYL)-10H-PHENOTHIAZINE
Systematic Name English
V0114CP
Common Name English
V-0114
Common Name English
V0114
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
Code System Code Type Description
INN
9172
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
PRIMARY
NCI_THESAURUS
C90859
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
PRIMARY
FDA UNII
5G2MWA892Y
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
PRIMARY
PUBCHEM
6992284
Created by admin on Sat Jun 26 11:45:50 UTC 2021 , Edited by admin on Sat Jun 26 11:45:50 UTC 2021
PRIMARY
EPA CompTox
88598-74-7
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
PRIMARY
CAS
88598-74-7
Created by admin on Sat Jun 26 11:45:49 UTC 2021 , Edited by admin on Sat Jun 26 11:45:49 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
TARGET -> INHIBITOR
Binds stronger than R-isomer
Related Record Type Details
ACTIVE MOIETY