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Details

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

SHOW SMILES / InChI
Structure of LEVAMLODIPINE

SMILES

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

InChI

InChIKey=HTIQEAQVCYTUBX-KRWDZBQOSA-N
InChI=1S/C20H25ClN2O5/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/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1

HIDE SMILES / InChI

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 23:48:58 UTC 2019
Edited
by admin
on Mon Oct 21 23:48:58 UTC 2019
Record UNII
0P6NLP6806
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVAMLODIPINE
INN   WHO-DD  
INN  
Official Name English
LEVAMLODIPINE [INN]
Common Name English
S-AMLODIPINE
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)-
Common Name English
3-ETHYL 5-METHYL (4S)-2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-6-METHYL-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE
Systematic Name English
AMLODIPINE, (S)-
Common Name English
LEVAMLODIPINE [WHO-DD]
Common Name English
Code System Code Type Description
MESH
C542574
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
CAS
103129-82-4
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
WIKIPEDIA
Levamlodipine
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
INN
8835
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
ChEMBL
CHEMBL2111097
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
EVMPD
SUB32938
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
DRUG BANK
DB09237
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
PUBCHEM
9822750
Created by admin on Mon Oct 21 23:48:58 UTC 2019 , Edited by admin on Mon Oct 21 23:48:58 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY