Levamlodipine maleateProduct ingredient for Levamlodipine

Name
Levamlodipine maleate
Drug Entry
Levamlodipine

Levamlodipine, also known as S-amlodipine, is a pharmacologically active enantiomer of amlodipine, an antihypertensive medication.8 Levamlodipine belongs to the dihydropyridine group of calcium channel blockers.8 This medication was first marketed in Russia and India before being granted FDA approval.9 The names S-amlodipine and levamlodipine may be used interchangeably as both substances are the same, however.8 As a racemic mixture, amlodipine contains (R) and (S)-amlodipine isomers, but only (S)-amlodipine as the active moiety possesses therapeutic activity.7

Levamlodipine was granted FDA approval on 19 December 2019.8

Accession Number
DBSALT002952
Structure
Synonyms
Levamlodipine maleate
UNII
12WW9T2ITA
CAS Number
135969-53-8
Weight
Average: 524.95
Monoisotopic: 524.1561582
Chemical Formula
C24H29ClN2O9
InChI Key
TZNOWAJJWCGILX-HNUXRKMMSA-N
InChI
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
IUPAC Name
(2Z)-but-2-enedioic acid; 3-ethyl 5-methyl (4S)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
SMILES
OC(=O)\C=C/C(O)=O.CCOC(=O)C1=C(COCCN)NC(C)=C([C@@H]1C1=C(Cl)C=CC=C1)C(=O)OC
ChemSpider
32698863
Predicted Properties
PropertyValueSource
Water Solubility0.0074 mg/mLALOGPS
logP2.22ALOGPS
logP1.64Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.62Chemaxon
pKa (Strongest Basic)9.45Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.88 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity108.64 m3·mol-1Chemaxon
Polarizability42.1 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon