Nisoldipine (CED0006717)

Record Information
Version1.0
Creation Date2016-05-22 03:44:21 UTC
Update Date2026-08-20 06:05:10 UTC
Accession NumberCHEM016809
Identification
Common NameNisoldipine
ClassSmall Molecule
Description
Nisoldipine is an organic compound with the formula C20H24N2O6 and an average molecular weight of 388.41 g/mol. Nisoldipine belongs to the hydropyridines, a subclass of pyridines and derivatives within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from 16 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically as calcium channel blockers, as well as food preservation within the food, food processing, and cookware category. Other recorded sources include household cleaning and consumer products—such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, other smoking requisites, and tobacco smoke filters—and electrical and electronic equipment, including amplifiers, antennas, electric switches, adjustable resistors, and conductors or conductive bodies characterised by the conductive materials. The recorded exposure route for this compound is oral. Nisoldipine interacts with five recorded protein targets. It acts as an inhibitor of the voltage-dependent L-type calcium channel subunit alpha-1D (CACNA1D), voltage-dependent L-type calcium channel subunit alpha-1S (CACNA1S), and voltage-dependent L-type calcium channel subunit alpha-1C (CACNA1C). Additionally, it targets the voltage-dependent calcium channel subunit alpha-2/delta-1 (CACNA2D1) and one other protein.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
SularKegg
NisoldipinHMDB
Bay K 5552HMDB
Chemical FormulaC20H24N2O6
Average Molecular Mass388.414 g/mol
Monoisotopic Mass388.163 g/mol
CAS Registry Number63675-72-9
IUPAC Name3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Namenisoldipine
SMILESCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OCC(C)C
InChI IdentifierInChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
InChI KeyVKQFCGNPDRICFG-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
  • Nitrobenzene
  • Nitroaromatic compound
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous amide
  • Organic nitro compound
  • Carboxylic acid ester
  • C-nitro compound
  • Amino acid or derivatives
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Allyl-type 1,3-dipolar organic compound
  • Secondary aliphatic amine
  • Enamine
  • Organic oxoazanium
  • Secondary amine
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Amine
  • 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 Solubility0.0058 g/LALOGPS
logP3.63ALOGPS
logP3.06ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)5.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.45 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.91 m³·mol⁻¹ChemAxon
Polarizability39.72 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 Spectrumsplash10-0adl-5059000000-15c76c3553190c789d84Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-7009000000-41eddaf4853ac4a37e28Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9004000000-c2d757da92039c3c78ebNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-e8dce16b1cdb4e9e030bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1009000000-44a09fee0814fad6e0a3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-3009000000-23e42ff91501270026ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-9044000000-ba0fba52523b1d58d5a8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0009000000-8fe78917ea0af1c8457fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0039000000-050b9d500d2bb8bbf4dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9030000000-f84f085e200cfb6a746aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0009000000-cba054bd2270a25fdb3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-0196000000-f5d5e228cc14d59c4ad1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2391000000-f0788a183fed36d34d93Not 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
1874.0Log mg/kg[1100:3300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
294Calcium channel blockersHealthcare, pharmaceuticals & veterinary productsNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)5.60514
Voltage-dependent L-type calcium channel subunit alpha-1C structureClick to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ13936HumansPredicted (SEA)0.155698
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CO35505Cavia porcellusPredicted (SEA)0.0778492
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)19.9294
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)12.5337
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)12.5337
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)0.622794
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q8BLA8Mus musculusPredicted (SEA)0.622794
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)61.3452
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP22002Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CQ14123HumansPredicted (SEA)1.94623
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP15381Oryctolagus cuniculusPredicted (SEA)0.233548
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)42.1164
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1DP27732Rattus norvegicusPredicted (SEA)0.0778492
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)11.5217
Click to view 3D structureCytochrome P450 2J2P51589HumansPredicted (SEA)0.389246
Potassium channel subfamily K member 2 structureClick to view 3D structurePotassium channel subfamily K member 2O95069HumansPredicted (SEA)0.155698
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)69.7529
Click to view 3D structurePotassium channel subfamily K member 2Q8HY88Bos taurusPredicted (SEA)0.0778492
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)58.1534
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)46.7095
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)49.4343
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)42.8949
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)73.5675
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)157.8
Concentrations
Not Available
External Links
DrugBank IDDB00401
HMDB IDHMDB0014545
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNisoldipine
Chemspider ID4343
ChEBI ID76917
PubChem Compound ID4499
Kegg Compound IDC07699
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hamilton SF, Houle LM, Thadani U: Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure. Heart Dis. 1999 Nov-Dec;1(5):279-88.
2. Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF: Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. Epub 2003 Oct 6.
3. Mielcarek J, Grobelny P, Szamburska O: The effect of beta-carotene on the photostability of nisoldipine. Methods Find Exp Clin Pharmacol. 2005 Apr;27(3):167-71.