Amlodipine (CHEM035841)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 06:42:49 UTC
Update Date2016-11-09 01:21:23 UTC
Accession NumberCHEM035841
Identification
Common NameAmlodipine
ClassSmall Molecule
DescriptionAmlodipine, initially approved by the FDA in 1987, is a popular antihypertensive drug belonging to the group of drugs called _dihydropyridine calcium channel blockers_. Due to their selectivity for the peripheral blood vessels, dihydropyridine calcium channel blockers are associated with a lower incidence of myocardial depression and cardiac conduction abnormalities than other calcium channel blockers . Amlodipine is commonly used in the treatment of high blood pressure and angina. Amlodipine has antioxidant properties and an ability to enhance the production of nitric oxide (NO), an important vasodilator that decreases blood pressure . The option for single daily dosing of amlodipine is an attractive feature of this drug .
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-9008000000-1fbca2d37d687cf7db0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4u-0192000000-988fbef9dd83defbfbe0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002o-1392000000-3e9bc5dcf61b0f4cae6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0092000000-ee62f2bc59215356e927Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-052r-0191000000-f2696d00f557899608c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - -1V, Positivesplash10-0a4u-0192000000-dbb503bf75ac45992a8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-2029500000-6f84285a27a09d3975adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw3-3189000000-2934b69ddcfba1ecb708Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ffx-3293000000-4459172f2e0c2c8495efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3007900000-5363cd8b8ca60ece4eeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4029200000-2a9e3badde424295bb13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9085000000-7db6de7520133d8f4045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1033900000-377f5862d692ece9b8b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6019200000-246c2de5f16d1f940e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-7093000000-e5145c0579c14e90d8d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0lxw-0049100000-fa18ab567110013335f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zor-0029100000-79f4e839da15602ebfb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-3495000000-4c7c1402fa10dd2c0919Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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