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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25ClN2O5.C4H4O4
Molecular Weight 524.948
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LEVAMLODIPINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CCOC(=O)C1=C(COCCN)NC(C)=C([C@@H]1C2=CC=CC=C2Cl)C(=O)OC

InChI

InChIKey=TZNOWAJJWCGILX-HNUXRKMMSA-N
InChI=1S/C20H25ClN2O5.C4H4O4/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21;5-3(6)1-2-4(7)8/h5-8,17,23H,4,9-11,22H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H25ClN2O5
Molecular Weight 408.876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Levalmodipine (S-amlodipine) is an active enantiomer of amlodipine, a calcium antagonist that inhibits the transmembrane influx of calcium ions into vascular smooth muscle and cardiac muscle. Experimental data suggest that S-amlodipine binds to both dihydropyridine and nondihydropyridine binding sites. The contractile processes of cardiac muscle and vascular smooth muscle are dependent upon the movement of extracellular calcium ions into these cells through specific ion channels. S-Amlodipine inhibits calcium ion influx across cell membranes selectively, with a greater effect on vascular smooth muscle cells than on cardiac muscle cells. Enantiomerically pure S-amlodipine is marketed in some countries worldwide, while racemate, containing active S-enantiomer an inactive R-enantiomer is marketed in the USA and indicated for the treatment of hypertension and coronary artery disease.

Approval Year

Substance Class Chemical
Created
by admin
on Mon Oct 21 23:48:55 UTC 2019
Edited
by admin
on Mon Oct 21 23:48:55 UTC 2019
Record UNII
12WW9T2ITA
Record Status Validated (UNII)
Record Version
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Name Type Language
LEVAMLODIPINE MALEATE
WHO-DD  
Common Name English
LEVAMLODIPINE MALEATE [WHO-DD]
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-1,4-DIHYDRO-6-METHYL-, 3-ETHYL 5-METHYL ESTER, (4S)-, (2Z)-2-BUTENEDIOATE (1:1)
Common Name English
Code System Code Type Description
EVMPD
SUB125921
Created by admin on Mon Oct 21 23:48:55 UTC 2019 , Edited by admin on Mon Oct 21 23:48:55 UTC 2019
PRIMARY
PUBCHEM
69165622
Created by admin on Mon Oct 21 23:48:55 UTC 2019 , Edited by admin on Mon Oct 21 23:48:55 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY