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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25ClN2O5.C6H6O3S.2H2O
Molecular Weight 603.082
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMLODIPINE BESYLATE DIHYDRATE

SMILES

O.O.OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C2=C(COCCN)NC(C)=C([C@@H]2C3=CC=CC=C3Cl)C(=O)OC

InChI

InChIKey=CXOUVSIRCRQEOE-FCQHKQNSSA-N
InChI=1S/C20H25ClN2O5.C6H6O3S.2H2O/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;7-10(8,9)6-4-2-1-3-5-6;;/h5-8,17,23H,4,9-11,22H2,1-3H3;1-5H,(H,7,8,9);2*1H2/t17-;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula C20H25ClN2O5
Molecular Weight 408.876
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity ( - )

Molecular Formula C6H6O3S
Molecular Weight 158.175
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 ng/mL
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens
2.71 ng/mL
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
161.7 ng × h/mL
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens
147.43 ng × h/mL
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
55 h
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens
45.1 h
5 mg single, oral
LEVAMLODIPINE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Substance Class Chemical
Record UNII
6WFN2P6FAQ
Record Status Validated (UNII)
Record Version