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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25ClN2O5.C4H6O5
Molecular Weight 542.963
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMLODIPINE MALATE

SMILES

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

InChI

InChIKey=ICLGPDCMPQYWIA-OSRSGTIQSA-N
InChI=1S/C20H25ClN2O5.C4H6O5/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;5-2(4(8)9)1-3(6)7/h5-8,17,23H,4,9-11,22H2,1-3H3;2,5H,1H2,(H,6,7)(H,8,9)/t17-;2-/m00/s1

HIDE SMILES / InChI

Molecular Formula C20H25ClN2O5
Molecular Weight 408.876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Cmax

ValueDoseCo-administeredAnalytePopulation
2.71 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TELMISARTAN
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.1 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
147.43 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TELMISARTAN
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
161.7 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45.1 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TELMISARTAN
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
55 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVAMLODIPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >50 uM]
no [IC50 >50 uM]
no [IC50 >50 uM]
no [IC50 >50 uM]
yes [IC50 40.12 uM]
yes [IC50 9.55 uM]
yes [Ki 21.45 uM]
yes [Ki 7.22 uM]
yes [Ki 8.95 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:21 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:21 GMT 2023
Record UNII
S0QL3IT20J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVAMLODIPINE MALATE
USAN   WHO-DD  
USAN  
Official Name English
LEVAMLODIPINE MALATE [USAN]
Common Name English
Levamlodipine malate [WHO-DD]
Common Name English
LEVAMLODIPINE L-MALATE
Common Name English
3-Ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate (2S)-hydroxybutanedioate (1:1)
Systematic Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-1,4-DIHYDRO-6-METHYL-, 3-ETHYL 5-METHYL ESTER, (4S)-, (2S)-HYDROXYBUTANEDIOATE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
Code System Code Type Description
CAS
736178-83-9
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
FDA UNII
S0QL3IT20J
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
PUBCHEM
46174133
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID10223804
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
USAN
RR-103
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
SMS_ID
300000044490
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
NCI_THESAURUS
C77826
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL2111097
Created by admin on Fri Dec 15 16:02:21 GMT 2023 , Edited by admin on Fri Dec 15 16:02:21 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY