Amlodipine (CED0001914)

Record Information
Version1.0
Creation Date2016-05-26 06:42:49 UTC
Update Date2026-08-20 06:10:04 UTC
Accession NumberCHEM035841
Identification
Common NameAmlodipine
ClassSmall Molecule
Description
Amlodipine is an organic compound with the formula C20H25ClN2O5 and an average molecular weight of 408.88 g/mol. Amlodipine belongs to the hydropyridines, a subclass of pyridines and derivatives within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from 25 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically calcium channel blockers, ACE inhibitors, beta blocking agents, agents acting on the renin-angiotensin system, and angiotensin ii receptor blockers (arbs). It is also associated with household cleaning and consumer products, such as bleaching agents, pipe accessories, other smoking requisites, non electric simulated smoking devices, and cigar cigarettes. Additional sources include food, food processing, and cookware, specifically food preservation and the preparation of wine or sparkling wine, as well as drinking water and water supply. It is further linked to electrical and electronic equipment, including antennas, electrodes, adjustable resistors, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. The recorded route of exposure for this compound is oral. Amlodipine interacts with nine recorded protein targets. It acts as a blocker or inhibitor of carbonic anhydrase 1 (CA1), as well as the voltage-dependent L-type calcium channel subunit alpha-1C (CACNA1C), the voltage-dependent N-type calcium channel subunit alpha-1B (CACNA1B), and the voltage-dependent L-type calcium channel subunit beta-1 (CACNB1), among five other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateChEBI
Amlodipine free baseChEBI
AmlodipinoChEBI
AmlodipinumChEBI
NorvascKegg
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acidGenerator
Amlodipine besilateHMDB
Amlodipine besylateHMDB
AMVAZHMDB
IstinHMDB
PelmecHMDB
Racemic amlodipineHMDB
Amlodipine, (+-)-isomerHMDB
Amlodipine, (+-)-isomer, maleate (1:1)HMDB
Amlodipine, (S)-isomer, maleate (1:1)HMDB
AmlorHMDB
Amlodipine, (R)-isomerHMDB
Pfizer brand OF amlodipine besilateHMDB
Amlodipine maleateHMDB
Amlodipine maleate (1:1)HMDB
AmlodisHMDB
AstudalHMDB
Mack brand OF amlodipine besilateHMDB
Almirall brand OF amlodipine besilateHMDB
Eczacibasi brand OF amlodipine besilateHMDB
Chemical FormulaC20H25ClN2O5
Average Molecular Mass408.876 g/mol
Monoisotopic Mass408.145 g/mol
CAS Registry Number88150-42-9
IUPAC Name3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Name(+-)-amlodipine
SMILESCCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC
InChI IdentifierInChI=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
InChI KeyHTIQEAQVCYTUBX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentDihydropyridinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dihydropyridinecarboxylic acid derivative
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Azacycle
  • Enamine
  • Ether
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Primary aliphatic amine
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0074 g/LALOGPS
logP2.22ALOGPS
logP1.64ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.12ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.88 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.64 m³·mol⁻¹ChemAxon
Polarizability42.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-003r-9008000000-1fbca2d37d687cf7db0bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4u-0192000000-988fbef9dd83defbfbe0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002o-1392000000-3e9bc5dcf61b0f4cae6aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0092000000-ee62f2bc59215356e927Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0191000000-f2696d00f557899608c4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4u-0192000000-dbb503bf75ac45992a8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-2029500000-6f84285a27a09d3975adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gw3-3189000000-2934b69ddcfba1ecb708Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ffx-3293000000-4459172f2e0c2c8495efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-3007900000-5363cd8b8ca60ece4eeaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-4029200000-2a9e3badde424295bb13Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-9085000000-7db6de7520133d8f4045Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1033900000-377f5862d692ece9b8b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6019200000-246c2de5f16d1f940e93Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-7093000000-e5145c0579c14e90d8d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0lxw-0049100000-fa18ab567110013335f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zor-0029100000-79f4e839da15602ebfb0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-3495000000-4c7c1402fa10dd2c0919Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
376.0Log mg/kg[210:670]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
293Beta blocking agentsHealthcare, pharmaceuticals & veterinary productsNot Available
294Calcium channel blockersHealthcare, pharmaceuticals & veterinary productsNot Available
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
296Angiotensin ii receptor blockers (arbs)Healthcare, pharmaceuticals & veterinary productsNot Available
297Agents acting on the renin-angiotensin systemHealthcare, pharmaceuticals & veterinary productsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Voltage-dependent L-type calcium channel subunit alpha-1C structureClick to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ13936HumansPredicted (SEA)0.700643
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CO35505Cavia porcellusPredicted (SEA)0.0778492
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)40.5594
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP22002Rattus norvegicusPredicted (SEA)0.934191
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)73.0226
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)37.9126
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)24.1333
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)27.87
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)32.1517
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)26.0016
Potassium channel subfamily K member 2 structureClick to view 3D structurePotassium channel subfamily K member 2O95069HumansPredicted (SEA)0.0778492
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)42.2721
Click to view 3D structurePotassium channel subfamily K member 2Q8HY88Bos taurusPredicted (SEA)0.0778492
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)77.7714
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)104.474
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)13.1565
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)347.208
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)95.2874
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q8BLA8Mus musculusPredicted (SEA)2.17978
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)372.119
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CQ14123HumansPredicted (SEA)10.0426
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)110.39
Voltage-dependent L-type calcium channel subunit alpha-1D structureClick to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1DQ01668HumansPredicted (SEA)0.311397
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP15381Oryctolagus cuniculusPredicted (SEA)2.33548
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1DP27732Rattus norvegicusPredicted (SEA)2.25763
Concentrations
Not Available
External Links
DrugBank IDDB00381
HMDB IDHMDB0005018
FooDB IDFDB023590
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID955
PDB IDNot Available
Wikipedia LinkAmlodipine
Chemspider ID2077
ChEBI ID2668
PubChem Compound ID2162
Kegg Compound IDC06825
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kim, Seok-Chan; Choi, Kwan-Min; Cheong, Chan-Seong. Synthesis of amlodipine using aza Diels-Alder reaction. Bulletin of the Korean Chemical Society (2002), 23(1), 143-144.
2. Iabichella ML, Dell'Omo G, Melillo E, Pedrinelli R: Calcium channel blockers blunt postural cutaneous vasoconstriction in hypertensive patients. Hypertension. 1997 Mar;29(3):751-6.
3. Pedrinelli R, Dell'Omo G, Nuti M, Menegato A, Balbarini A, Mariani M: Heterogeneous effect of calcium antagonists on leg oedema: a comparison of amlodipine versus lercanidipine in hypertensive patients. J Hypertens. 2003 Oct;21(10):1969-73.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1532771
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16422032
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1834846
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19450066
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21591999
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7522286
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8310972
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=8310973
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9156957