Felodipine (CHEM016707)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:41:05 UTC
Update Date2016-11-09 01:15:27 UTC
Accession NumberCHEM016707
Identification
Common NameFelodipine
ClassSmall Molecule
DescriptionFelodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, felodipine prevents calcium-dependent myocyte contraction and vasoconstriction. Felodipine is the most potent CCB in use and is unique in that it exhibits fluorescent activity. In addition to binding to L-type calcium channels, felodipine binds to a number of calcium-binding proteins, exhibits competitive antagonism of the mineralcorticoid receptor, inhibits the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase, and blocks calcium influx through voltage-gated T-type calcium channels. Felodipine is used to treat mild to moderate essential hypertension.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylateChEBI
3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylateChEBI
4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl esterChEBI
FelodipinaChEBI
FelodipinumChEBI
PlendilKegg
(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acidGenerator
3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylic acidGenerator
4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate ethyl methyl esterGenerator
DL-FelodipineHMDB
1a Brand OF felodipineHMDB
Alpharma brand OF felodipineHMDB
AstraZeneca brand OF felodipineHMDB
Azupharma brand OF felodipineHMDB
Felo biochemieHMDB
Felo purenHMDB
FelobetaHMDB
FelodurHMDB
Heumann brand OF felodipineHMDB
Hoechst brand OF felodipineHMDB
Pharmacia spain brand OF felodipineHMDB
TheraPharm brand OF felodipineHMDB
Felo-purenHMDB
FelocorHMDB
Felodipin heumannHMDB
Felodipin stadaHMDB
Felodipin duraHMDB
MunobalHMDB
Pharmaceutica astra brand OF felodipineHMDB
Wörwag brand OF felodipineHMDB
CT Arzneimittel brand OF felodipineHMDB
CT-Arzneimittel brand OF felodipineHMDB
Aliud brand OF felodipineHMDB
Alphapharm brand OF felodipineHMDB
Astra brand OF felodipineHMDB
BC Brand OF felodipineHMDB
Felodipin alHMDB
Felodipin azuHMDB
Felodipin ratiopharmHMDB
Merck dura brand OF felodipineHMDB
PerfudalHMDB
Promed brand OF felodipineHMDB
Stadapharm brand OF felodipineHMDB
Betapharm brand OF felodipineHMDB
Felodipin von CTHMDB
AbZ brand OF felodipineHMDB
AgonHMDB
Aventis brand OF felodipineHMDB
Felodipin 1a pharmaHMDB
Felodipin abzHMDB
Felodipin-ratiopharmHMDB
FelogammaHMDB
FenselHMDB
FlodilHMDB
Heumann, felodipinHMDB
Hexal brand OF felodipineHMDB
ModipHMDB
RenedilHMDB
Ratiopharm brand OF felodipineHMDB
Von CT, felodipinHMDB
Chemical FormulaC18H19Cl2NO4
Average Molecular Mass384.254 g/mol
Monoisotopic Mass383.069 g/mol
CAS Registry Number72509-76-3
IUPAC Name3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Namefelodipine
SMILESCCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC
InChI IdentifierInChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3
InChI KeyRZTAMFZIAATZDJ-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
  • 1,2-dichlorobenzene
  • 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
  • Secondary aliphatic amine
  • Enamine
  • Secondary amine
  • Azacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Organohalogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organochloride
  • 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 Solubility0.0072 g/LALOGPS
logP4.36ALOGPS
logP3.44ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)5.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.2 m³·mol⁻¹ChemAxon
Polarizability38.04 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, Positivesplash10-01t9-3009000000-5b611cdc2d075de69610Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000j-0922000000-9b26b987caa87b8a13afSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udu-0139000000-085071c20c5d0c134d8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-0019000000-33bf0db3bf36f29993fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0095000000-c27a529dc8d62e0c3663Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0490000000-b027fd5c39a74d5a8983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-74fea585f5eab97e301dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0029000000-611d97581685b1d82833Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0wbc-1095000000-178af93061f6d2ad0db1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0009000000-88f48d1738d7c1f69a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-0129000000-d31431a7eda7ca7396bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0piu-0982000000-98f7be8fe67f962d9ef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-e514f5ea1713c07d88b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2009000000-409c00755f945e97a932Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9280000000-97534f29e936d15877c7Spectrum
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 IDDB01023
HMDB IDHMDB0015158
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFelodipine
Chemspider ID3216
ChEBI ID585948
PubChem Compound ID3333
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dunselman PH, Edgar B: Felodipine clinical pharmacokinetics. Clin Pharmacokinet. 1991 Dec;21(6):418-30.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18457386