U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=C(Cl)C=CC=C2)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 No
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 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 16:19:32 GMT 2023
Edited
by admin
on Fri Dec 15 16:19:32 GMT 2023
Record UNII
12WW9T2ITA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVAMLODIPINE MALEATE
WHO-DD  
USAN  
Official 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
CONJUPRI
Brand Name English
Levamlodipine maleate [WHO-DD]
Common Name English
LEVAMLODIPINE MALEATE [USAN]
Common Name English
3-ETHYL 5-METHYL (4S)-2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-6-METHYL-1,4-DIHYDROPYRIDINE-3,5-DICARBOXYLATE (2Z)-BUT-2-ENEDIOATE
Systematic Name English
AMLODIPINE MALEATE, S-
Common Name English
LEVAMLODIPINE MALEATE [ORANGE BOOK]
Common Name English
Code System Code Type Description
CAS
135969-53-8
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID801027742
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
EVMPD
SUB125921
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
NCI_THESAURUS
C175110
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
RXCUI
2377031
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
USAN
HI-46
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
FDA UNII
12WW9T2ITA
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
SMS_ID
100000151631
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
PUBCHEM
69165622
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
DAILYMED
12WW9T2ITA
Created by admin on Fri Dec 15 16:19:32 GMT 2023 , Edited by admin on Fri Dec 15 16:19:32 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY