Nicardipine (CED0003615)

Record Information
Version1.0
Creation Date2016-05-22 03:44:05 UTC
Update Date2026-08-22 06:30:19 UTC
Accession NumberCHEM016803
Identification
Common NameNicardipine
ClassSmall Molecule
Description
Nicardipine is an organic compound with the formula C26H29N3O6 and an average molecular weight of 479.52 g/mol. Nicardipine belongs to the hydropyridines, a subclass of pyridines and derivatives within the organic compounds. It is classified as an organoheterocyclic compound. This substance is recorded as being released from or found in 12 sources. These include healthcare, pharmaceuticals and veterinary products as calcium channel blockers, as well as food, food processing and cookware involving food preservation and the preparation of wine or sparkling wine. Other sources include household cleaning and consumer products such as perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, and other smoking requisites. It is also associated with electrical and electronic equipment, specifically electrodes, hybrid capacitors, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. Exposure routes for the compound include oral and intravenous administration. Nicardipine acts on 31 recorded protein targets, serving as an antagonist, inhibitor, or other unknown regulator. These targets include the alpha-1A adrenergic receptor (ADRA1A), dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A (PDE1A), dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B (PDE1B), and voltage-dependent L-type calcium channel subunit alpha-1C (CACNA1C), among 27 other proteins. Regarding health effects, nicardipine is used as a treatment for hypertension (PMC5698911), as well as dementia (PMC12454544) and memory loss (PMC12454544).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
CardeneKegg
FlusemideHMDB
LA, nicardipineHMDB
LincilHMDB
LucenfalHMDB
Nicardipine hydrochlorideHMDB
Nicardipino ratiopharmHMDB
Novartis brand OF nicardipine hydrochlorideHMDB
Roche brand OF nicardipine hydrochlorideHMDB
Tedec meiji brand OF nicardipine hydrochlorideHMDB
Yamanouchi brand 3 OF nicardipine hydrochlorideHMDB
Farma lepori brand OF nicardipine hydrochlorideHMDB
LoxenHMDB
Ratiopharm brand OF nicardipine hydrochlorideHMDB
RideneHMDB
Seid brand OF nicardipineHMDB
Solvay brand OF nicardipine hydrochlorideHMDB
Syntex brand OF nicardipine hydrochlorideHMDB
UCB brand OF nicardipine hydrochlorideHMDB
VasonaseHMDB
Cardene i.v.HMDB
Cardene SRHMDB
DaganHMDB
Nicardipine seid brandHMDB
Nicardipino seidHMDB
PerdipineHMDB
Yamanouchi brand 2 OF nicardipine hydrochlorideHMDB
Almirall brand OF nicardipine hydrochlorideHMDB
AntagonilHMDB
ESP pharma brand OF nicardipine hydrochlorideHMDB
Hydrochloride, nicardipineHMDB
LecibralHMDB
Nicardipine laHMDB
Yamanouchi brand 1 OF nicardipine hydrochlorideHMDB
Chemical FormulaC26H29N3O6
Average Molecular Mass479.525 g/mol
Monoisotopic Mass479.206 g/mol
CAS Registry Number55985-32-5
IUPAC Name3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Namenicardipine
SMILESCOC(=O)C1=C(C)NC(C)=C(C1C1=CC(=CC=C1)[N+]([O-])=O)C(=O)OCCN(C)CC1=CC=CC=C1
InChI IdentifierInChI=1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3
InChI KeyZBBHBTPTTSWHBA-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
  • Benzylamine
  • Phenylmethylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Methyl ester
  • Vinylogous amide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • C-nitro compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic zwitterion
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.0025 g/LALOGPS
logP4.34ALOGPS
logP3.56ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)8.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area113.69 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity134.8 m³·mol⁻¹ChemAxon
Polarizability49.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00kg-6945600000-88fa08ae55dce8fa50bbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2930000000-9730aac08522ec25e87bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1930000000-281a892aa3ef3862da09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0921000000-cb717805fcb949f5cd9aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-2940000000-aa69d5c0a6969ff1eda8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2940000000-12b6cb09ae1c275c7673Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-7396000000-c37106851497811f1562Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0101900000-a42f7527bca4c5356250Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9410000000-9b61ce9910712434cbf1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9230000000-0639e2b5cef885fc94e3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0503900000-381c26b1efa1dc70b309Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1609000000-ec654bea9500a31f81d3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9160000000-abe9ea0826770248f05aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9476000000-c1b72913df485a05a9f5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0101900000-7acc467f68a49da381e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0609100000-d1f0dc228a16564ab569Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1609000000-500b44165886e391edd4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-2940000000-e613896be89cd6b8fc75Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0000900000-fa29fcb6e7ce3db6662fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0000900000-8be9abda1139b11b5a6fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-5973800000-d273cf4770983e873feaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-b1a63db11b02197bfca2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-336ef9a38bbb2a65be23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0016-5294800000-0cd026f9bd2da079e049Not 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
238.0Log mg/kg[130:420]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionis_treatment_forNot AvailablePMC5698911
dementiais_treatment_forNot AvailablePMC12454544
memory lossis_treatment_forNot AvailablePMC12454544
low compliance bladderis_treatment_forNot AvailablePMC12454544
Exposure Sources
Source IDSourceSectorReference
294Calcium channel blockersHealthcare, pharmaceuticals & veterinary productsNot 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
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot 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
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)2.02408
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)1.63483
Voltage-dependent L-type calcium channel subunit alpha-1C structureClick to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ13936HumansPredicted (SEA)0.0778492
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)4.28171
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)3.73676
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q8BLA8Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureEquilibrative nucleoside transporter 1O54698Rattus norvegicusPredicted (SEA)0.0778492
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)24.7561
Click to view 3D structureCytochrome P450 2J2P51589HumansPredicted (SEA)0.155698
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)11.2881
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)27.4029
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)17.9832
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)18.606
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)14.6357
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)12.5337
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)14.7914
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP15381Oryctolagus cuniculusPredicted (SEA)0.233548
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CQ14123HumansPredicted (SEA)1.55698
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)42.4278
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CO35505Cavia porcellusPredicted (SEA)0.233548
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)2.88042
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)3.42537
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP22002Rattus norvegicusPredicted (SEA)1.32344
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1DP27732Rattus norvegicusPredicted (SEA)0.155698
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)107.977
Concentrations
Not Available
External Links
DrugBank IDDB00622
HMDB IDHMDB0014760
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNicardipine
Chemspider ID4319
ChEBI ID507549
PubChem Compound ID4474
Kegg Compound IDC07264
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References