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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25ClN2O5
Molecular Weight 408.876
Optical Activity ( - )
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=C(Cl)C=CC=C2)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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Cmax

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

AUC

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

T1/2

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

Drug as perpetrator​

Drug as victim

Substance Class Chemical
Record UNII
0P6NLP6806
Record Status Validated (UNII)
Record Version