Isradipine (CHEM016744)

Record Information
Version1.0
Creation Date2016-05-22 03:42:09 UTC
Update Date2026-08-20 03:08:12 UTC
Accession NumberCHEM016744
Identification
Common NameIsradipine
ClassSmall Molecule
Description
Isradipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. It is structurally related to felodipine, nifedipine, and nimodipine and is the most potent calcium-channel blocking agent of the DHP class. Isradipine binds to calcium channels with high affinity and specificity and inhibits calcium flux into cardiac and arterial smooth muscle cells. It exhibits greater selectivity towards arterial smooth muscle cells owing to alternative splicing of the alpha-1 subunit of the channel and increased prevalence of inactive channels in smooth muscle cells. Isradipine may be used to treat mild to moderate essential hypertension.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DynacircKegg
(+/-)-isradipineHMDB
IsradipinHMDB
IsrodipineHMDB
Isradipine, (+-)-isomerMeSH, HMDB
Isradipine, (R)-isomerMeSH, HMDB
Isradipine, (S)-isomerMeSH, HMDB
LomirMeSH, HMDB
Chemical FormulaC19H21N3O5
Average Molecular Mass371.387 g/mol
Monoisotopic Mass371.148 g/mol
CAS Registry Number75695-93-1
IUPAC Name3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Nameisradipine
SMILESCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C
InChI IdentifierInChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3
InChI KeyHMJIYCCIJYRONP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxadiazoles. These are organic compounds containing a benzene fused to an oxadiazole ring (a five-membered ring with two carbon atoms, one nitrogen atom, and one oxygen atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxadiazoles
Sub ClassNot Available
Direct ParentBenzoxadiazoles
Alternative Parents
Substituents
  • Benzoxadiazole
  • Dihydropyridinecarboxylic acid derivative
  • Dihydropyridine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Hydropyridine
  • Azole
  • Heteroaromatic compound
  • Furazan
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Oxadiazole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Azacycle
  • Enamine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.23 g/LALOGPS
logP3ALOGPS
logP2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)5.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.55 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.08 m³·mol⁻¹ChemAxon
Polarizability37.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
External Links
DrugBank IDDB00270
HMDB IDHMDB0249193
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsradipine
Chemspider ID3652
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References