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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25ClN2O5.C6H5NO2
Molecular Weight 531.985
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVAMLODIPINE NICOTINATE

SMILES

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

InChI

InChIKey=VLDHKVLFLLOUKI-LMOVPXPDSA-N
InChI=1S/C20H25ClN2O5.C6H5NO2/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;8-6(9)5-2-1-3-7-4-5/h5-8,17,23H,4,9-11,22H2,1-3H3;1-4H,(H,8,9)/t17-;/m0./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 C6H5NO2
Molecular Weight 123.1094
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Sat Dec 16 18:21:26 GMT 2023
Edited
by admin
on Sat Dec 16 18:21:26 GMT 2023
Record UNII
7EQG8Y8AHW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVAMLODIPINE NICOTINATE
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)-, MONO-3-PYRIDINECARBOXYLATE
Systematic Name English
S Amlodipine Nicotinate [WHO-DD]
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)-, 3-PYRIDINECARBOXYLATE (1:1)
Systematic Name English
(-)-AMLODIPINE NICOTINATE
Common Name English
(S)-Amlodipine Nicotinate
Common Name English
Code System Code Type Description
PUBCHEM
9871695
Created by admin on Sat Dec 16 18:21:26 GMT 2023 , Edited by admin on Sat Dec 16 18:21:26 GMT 2023
PRIMARY
SMS_ID
100000175610
Created by admin on Sat Dec 16 18:21:26 GMT 2023 , Edited by admin on Sat Dec 16 18:21:26 GMT 2023
PRIMARY
CAS
675605-61-5
Created by admin on Sat Dec 16 18:21:26 GMT 2023 , Edited by admin on Sat Dec 16 18:21:26 GMT 2023
PRIMARY
FDA UNII
7EQG8Y8AHW
Created by admin on Sat Dec 16 18:21:26 GMT 2023 , Edited by admin on Sat Dec 16 18:21:26 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY