Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22N2S |
| Molecular Weight | 322.467 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C([C@@H]1CN2CCC1CC2)N3C4=CC=CC=C4SC5=CC=CC=C35
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
| Molecular Formula | C20H22N2S |
| Molecular Weight | 322.467 |
| 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.
CNS Activity
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27488192
Single doses of 2.5, 5.0 and 10 mg
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:23:36 GMT 2025
by
admin
on
Mon Mar 31 18:23:36 GMT 2025
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| Record UNII |
5G2MWA892Y
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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9172
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C90859
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5G2MWA892Y
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6992284
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DTXSID4048771
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300000034331
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88598-74-7
Created by
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| Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER | |||
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TARGET -> INHIBITOR |
Binds stronger than R-isomer
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |