Amlodipine

Title: Amlodipine
CAS Registry Number: 88150-42-9
CAS Name: 2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester
Additional Names: (±)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine
Manufacturers' Codes: UK-48340
Molecular Formula: C20H25ClN2O5
Molecular Weight: 408.88
Percent Composition: C 58.75%, H 6.16%, Cl 8.67%, N 6.85%, O 19.56%
Literature References: Dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer. Prepn: S. F. Campbell et al., EP 89167; eidem, US 4572909 (1983, 1986 both to Pfizer). Synthesis and pharmacology of racemate and enantiomers: J. E. Arrowsmith et al., J. Med. Chem. 29, 1696 (1986). Calcium antagonist activity: R. A. Burges et al., J. Cardiovasc. Pharmacol. 9, 110 (1987). GC determn in plasma: A. P. Beresford et al., J. Chromatogr. 420, 178 (1987). Metabolism: idem et al., Xenobiotica 18, 245 (1988). Review of pharmacology and therapeutic efficacy: M. Haria, A. J. Wagstaff, Drugs 50, 560-586 (1995). Clinical potential in severe heart failure: M. Packer et al., N. Engl. J. Med. 335, 1107 (1996). Review of mechanism of plaque stabilization: R. P. Mason, Atherosclerosis 165, 191-199 (2002); of clinical potential in combination with atorvastatin in atherosclerosis: J. W. Jukema, J. W. A. van der Hoorn, Expert Opin. Pharmacother. 5, 459-468 (2004).
Derivative Type: Maleate
CAS Registry Number: 88150-47-4
Manufacturers' Codes: UK-48340-11
Molecular Formula: C20H25ClN2O5.C4H4O4
Molecular Weight: 524.95
Percent Composition: C 54.91%, H 5.57%, Cl 6.75%, N 5.34%, O 27.43%
Properties: White crystals from ethyl acetate, mp 178-179°.
Melting point: mp 178-179°
Derivative Type: Benzenesulfonate
CAS Registry Number: 111470-99-6
Additional Names: Amlodipine besylate
Manufacturers' Codes: UK-48340-26
Trademarks: Amlor (Pfizer); Antacal (Errekappa); Istin (Pfizer); Monopina (Bioindustria); Norvasc (Pfizer)
Molecular Formula: C20H25ClN2O5.C6H5SO3H
Molecular Weight: 567.05
Percent Composition: C 55.07%, H 5.51%, Cl 6.25%, N 4.94%, O 22.57%, S 5.65%
Properties: White crystalline powder. Slightly sol in water; sparingly sol in ethanol.
Therap-Cat: Antianginal; antihypertensive.
Keywords: Antianginal; Antihypertensive; Dihydropyridine Derivatives; Calcium Channel Blocker; Dihydropyridine Derivatives.
Ammonia Ammonia Water Ammoniacum Ammonium Acetate Ammonium Benzoate

Amlodipine
Amlodipine Structural Formulae.png
Amlodipine 3d structure.png
Systematic (IUPAC) name
(RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a692044
Licence data US FDA:link
Pregnancy cat. C (AU) C (US)
Legal status POM (UK) -only (US)
Routes Oral (tablets)
Pharmacokinetic data
Bioavailability 64 to 90%
Metabolism Hepatic
Half-life 30 to 50 hours
Excretion Renal
Identifiers
CAS number 88150-42-9 YesY
ATC code C08CA01
PubChem CID 2162
DrugBank DB00381
ChemSpider 2077 YesY
UNII 1J444QC288 YesY
KEGG D07450 YesY
ChEBI CHEBI:2668 YesY
ChEMBL CHEMBL1491 YesY
Chemical data
Formula C20H25ClN2O5 
Mol. mass 408.879 g/mol
 YesY (what is this?)  (verify)

Amlodipine (Norvasc (Pfizer) and generics) (as besylate, mesylate or maleate) is a long-acting dihydropyridine-type (DHP) calcium channel blocker used to lower blood pressure and to treat anginal chest pain. Like other calcium channel blockers, amlodipine lowers blood pressure by relaxing arterial smooth muscles, which decreases total peripheral resistance and therefore reduces blood pressure. In angina, amlodipine increases blood flow to the heart muscle (although DHP-class calcium channel blockers are more selective for arteries than the muscular tissue of the heart (myocardium), as the calcium ion channels of the heart are not of the dihydropyridine-type).