Drug Details

General Information of the Drug (ID: DR0775)
Name
Amlodipine
Synonyms
amlodipine; 88150-42-9; Norvasc; AMLODIPINE BASE; Amlodipino; Amlodipinum; Caduet; Istin; Amlodipine Free Base; Amlodipine besilate; Amvaz; Amlodis; CHEBI:2668; 3-ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; Norvasc (TN); Amlocard; Coroval; Lipinox; 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; UK-4834011; Amlor; Amlodipinum [Latin]; Amlodipino [Spanish]; 88150-42-9 (free base); Amdepin; Amdipin; Amlodin; Pelmec; MFCD00864687; 3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; Amlodipine [INN:BAN]; Racemic Amlodipine; (RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; C20H25ClN2O5; 3-ethyl 5-methyl 2-{[(2-aminoethyl)oxy]methyl}-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; 3-O-ethyl 5-O-methyl 4-(2-chlorophenyl)-1-deuterio-2-[2-(dideuterioamino)ethoxymethyl]-6-methyl-4H-pyridine-3,5-dicarboxylate; O3-ethyl O5-methyl 2-(2-azanylethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; SR-05000001461; NCGC00165957-04; r-amlodipine; Amlodipine/; Amlodipine D4; HSDB 7079; 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine; 2-[2-aminoethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine; 3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester; amlodipine (NORVASC); Amlodipine (USP/INN); (R)-Amlodipine-[d4]; 2-[(2-Aminoethoxy)-methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5- pyridinedicarboxylic acid 3-ethyl 5-methyl ester benzene sulfonate; Spectrum2_000486; Spectrum3_001004; Spectrum4_001132; Spectrum5_001550; EC 425-820-1; CHEMBL1491; SCHEMBL26478; BSPBio_002727; KBioGR_001643; MLS001401409; BIDD:GT0810; SPBio_000351; GTPL6981; CHEMBL3211346; CHEMBL3304444; DTXSID7022596; KBio3_001947; Copalia (amlodipine + valsartan); HGP0904; BCPP000403; HMS2052N03; HMS2089H07; HMS2231K08; HMS3370G17; HMS3394N03; HMS3651I04; HMS3713C10; ALBB-027270; BCP02420; HGP-0904; HY-B0317; ABP000734; BBL023710; BDBM50088383; CA0134; s1905; STL356053; CKD-330 COMPONENT AMLODIPINE; AKOS015843475; AC-4535; BCP9000295; CCG-101157; CCG-220414; DB00381; MCULE-8264151664; NC00407; NCGC00165957-01; NCGC00165957-02; NCGC00165957-03; NCGC00165957-05; NCGC00165957-07; 3-Ethyl 5-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate; 3-Ethyl-5-methyl (+-)-2-((2-aminoethoxy)methyl)-4-(2-chlorphenyl)-1,4-dihydro-6-methyl-3,5-pyridindicarboxylat; 3-Ethyl-5-methyl (+-)-2-((2-aminoethoxymethyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate; 3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate; AK163198; Amlodipine 100 microg/mL in Acetonitrile; AS-13747; CPD000469198; K577; O3-ethyl O5-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate; SMR000469198; SY104813; AB0008128; UK-48,340; FT-0602653; FT-0657130; FT-0662111; FT-0662112; R3932; SW220228-1; 50A429; C06825; D07450; J10237; W-3152; AB01209618-01; AB01274726-01; AB01274726-02; AB01274726_03; AB01274726_04; AB01274726_05; A800681; Q411347; Katerzia&reg (amlodipine oral suspension, 1 mg/mL); SR-05000001461-3; SR-05000001461-4; SR-05000001461-5; BRD-A22032524-074-02-4; BRD-A22032524-074-03-2; BRD-A22032524-074-04-0; 2-(2-aminoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine; 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid O3-ethyl ester O5-methyl ester; 2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methylester; 2-[2-Aminoethoxymethyl]-3-ethoxycarbonyl-4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine; 3,5-pyridinedicarboxylic acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, benzene sulfonate; 3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate benzene sulfonate; 3-Ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorphenyl)-6-methyl-1,4-dihydropyridin-3,5-dicarboxylat; 3-Ethyl 5-methylester, (+/-)-2-[(2-aminoethoxy)methyl]-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate; 3-Ethyl-5-methyl (.+/-.)-2-[(2-aminoethoxy)methyl]-4-(o-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate
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Molecular Type
Small molecule
Disease Hypertension [ICD-11: BA00] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 8.8-45.8 mcg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 3.5 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
The bioavailability of drug is 30%
Clearance
The total body clearance of drug is 7 +/- 1.3 mL/min/kg
Elimination
10% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 30C50 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.3494 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.005%
Vd
The volume of distribution (Vd) of drug is 21 L/kg
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H25ClN2O5
PubChem CID
2162
Canonical SMILES
CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
InChI
1S/C20H25ClN2O5/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/h5-8,17,23H,4,9-11,22H2,1-3H3
InChIKey
HTIQEAQVCYTUBX-UHFFFAOYSA-N
CAS Number
CAS 88150-42-9
ChEBI ID
CHEBI:2668
TTD Drug ID
D08JIV
DrugBank ID
DB00381
Target and Pathway
Target(s) Calcium channel alpha-2/delta-1 (CACNA2D1)  Molecule Info  [2]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Cardiac muscle contraction
3 Adrenergic signaling in cardiomyocytes
4 Oxytocin signaling pathway
5 Hypertrophic cardiomyopathy (HCM)
6 Arrhythmogenic right ventricular cardiomyopathy (ARVC)
7 Dilated cardiomyopathy
Panther Pathway Muscarinic acetylcholine receptor 2 and 4 signaling pathway Click to Show/Hide
WikiPathways Arrhythmogenic Right Ventricular Cardiomyopathy Click to Show/Hide
2 miR-targeted genes in muscle cell - TarBase
3 miR-targeted genes in lymphocytes - TarBase
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6981).
Reference 2 A first drug combination for the treatment of arterial hypertension with a calcium channel antagonist (amlodipine besylate) and an angiotensin receptor blocker (valsartan): Exforge. Rev Med Liege. 2007 Nov;62(11):688-94.