Nimodipine (CED0003038)

Record Information
Version1.0
Creation Date2016-05-22 03:44:20 UTC
Update Date2026-08-21 19:23:26 UTC
Accession NumberCHEM016808
Identification
Common NameNimodipine
ClassSmall Molecule
Description
Nimodipine is an organic compound with the formula C21H26N2O7 and an average molecular weight of 418.44 g/mol. Nimodipine belongs to the hydropyridines, a subclass of pyridines and derivatives within the organic compounds. It functions as a biological inhibitor (PMC7589057) and acts as an agonist, antagonist, or inhibitor of ten recorded protein targets, including the mineralocorticoid receptor (NR3C2) and voltage-dependent L-type calcium channel subunits alpha-1C (CACNA1C), alpha-1S (CACNA1S), and alpha-1D (CACNA1D). In terms of health effects, nimodipine is used as a treatment for ischemic stroke (PMC11127604) and has a therapeutic effect on blood pressure (PMC5414723). It is classified as a calcium channel blocker and is administered via oral or intravenous exposure routes. Nimodipine is found in or released from ten recorded sources. These include healthcare, pharmaceuticals, and veterinary products; food preservation within food, food processing, and cookware; ceilings in building and construction; and household cleaning and consumer products such as tobacco smoke filters and non-electric simulated smoking devices. Additionally, it is associated with electrical and electronic equipment, including electrodes, antennas, amplifiers, electrically stimulated smoking devices, and conductors or conductive bodies characterized by the conductive materials.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-beta-methoxyethyl ester 5-isopropyl esterChEBI
BAY e 9736ChEBI
Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylateChEBI
Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylateChEBI
NimodipinoChEBI
NimodipinumChEBI
NimotopChEBI
PeriplumChEBI
NymalizeKegg
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 3-b-methoxyethyl ester 5-isopropyl esterGenerator
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 3-beta-methoxyethyl ester 5-isopropyl esterGenerator
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 3-β-methoxyethyl ester 5-isopropyl esterGenerator
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-b-methoxyethyl ester 5-isopropyl esterGenerator
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-methoxyethyl ester 5-isopropyl esterGenerator
Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acidGenerator
Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylic acidGenerator
Andromaco brand OF nimodipineHMDB
Bayvit, nimodipinoHMDB
Cantabria brand OF nimodipineHMDB
Hexal, nimodipinHMDB
Alpharma brand OF nimodipineHMDB
Bayvit brand OF nimodipineHMDB
KenesilHMDB
AdmonHMDB
BrainalHMDB
ModusHMDB
Nimodipin hexalHMDB
Nimodipin-isisHMDB
NimodipinISISHMDB
Nimodipino bayvitHMDB
Vita brand OF nimodipineHMDB
e 9736, BayHMDB
9736, Bay eHMDB
Almirall brand OF nimodipineHMDB
Bayer brand OF nimodipineHMDB
CalnitHMDB
Elan brand OF nimodipineHMDB
Esteve brand OF nimodipineHMDB
Hexal brand OF nimodipineHMDB
Nimodipin isisHMDB
RemontalHMDB
Chemical FormulaC21H26N2O7
Average Molecular Mass418.440 g/mol
Monoisotopic Mass418.174 g/mol
CAS Registry Number66085-59-4
IUPAC Name3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Namenimodipine
SMILESCOCCOC(=O)C1=C(C)NC(C)=C(C1C1=CC(=CC=C1)[N+]([O-])=O)C(=O)OC(C)C
InChI IdentifierInChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3
InChI KeyUIAGMCDKSXEBJQ-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
  • Vinylogous amide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • C-nitro compound
  • Organic nitro compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Enamine
  • Ether
  • Azacycle
  • Organic 1,3-dipolar compound
  • Organic oxoazanium
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Roles
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 Solubility0.012 g/LALOGPS
logP3.41ALOGPS
logP2.54ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)5.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area119.68 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity112.38 m³·mol⁻¹ChemAxon
Polarizability43.17 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 Spectrumsplash10-0f6y-8009000000-df297acbb119ead19ae2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0149000000-2a019013c0386ca13362Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfu-0039000000-4fc95af4f67b0afb5234Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01bc-1654900000-b2486a1feba93aef89faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-5000900000-12c2938a62c8cb238e76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-9002600000-b69caecacf04408cf15bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-9000000000-58c041d65b909517cc19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3000900000-d333c69b2de3907d9af1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-9000600000-d1954bdf68414fdaddb4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-3a47cedd9c89d41d9be5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0004900000-aedc1fdb52380276f236Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-6049500000-b4e1452bef00eb5c76e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9020000000-24deee9cc6a1174c9f27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-0009400000-10fb7090b7ccce0b345eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ap3-0079100000-d496424ed4e3b7807f28Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kdi-0098000000-cae1334e08a3166f17baNot 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
1453.0Log mg/kg[820:2600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
blood pressurehas_therapeutic_effect_onNot AvailablePMC5414723
ischemic strokeis_treatment_forNot AvailablePMC11127604
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
294Calcium channel blockersHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot 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
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold 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
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Nimodipine Action Pathway
Nimodipine Action Pathway
Nimodipine Action Pathway (New)
Nimodipine Action Pathway (New)
Nimodipine Drug Metabolism Action Pathway
Nimodipine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)3.11397
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)4.12601
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)3.03612
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q8BLA8Mus musculusPredicted (SEA)0.0778492
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)2.80257
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CQ14123HumansPredicted (SEA)0.155698
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)24.0554
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)0.544945
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CO35505Cavia porcellusPredicted (SEA)0.0778492
Click to view 3D structureCytochrome P450 2J2P51589HumansPredicted (SEA)0.155698
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP15381Oryctolagus cuniculusPredicted (SEA)0.0778492
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)29.5827
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)37.2898
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)25.5345
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)17.5161
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)26.2352
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)19.8516
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1DP27732Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)23.5105
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)50.4463
3',5'-cyclic-AMP phosphodiesterase 4D structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4DQ08499HumansPredicted (SEA)10.3539
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)20.3965
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP22002Rattus norvegicusPredicted (SEA)1.63483
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AP54750HumansPredicted (SEA)2.72472
Concentrations
Not Available
External Links
DrugBank IDDB00393
HMDB IDHMDB0014537
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNimodipine
Chemspider ID4341
ChEBI ID7575
PubChem Compound ID4497
Kegg Compound IDC07267
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Allen GS, Ahn HS, Preziosi TJ, Battye R, Boone SC, Boone SC, Chou SN, Kelly DL, Weir BK, Crabbe RA, Lavik PJ, Rosenbloom SB, Dorsey FC, Ingram CR, Mellits DE, Bertsch LA, Boisvert DP, Hundley MB, Johnson RK, Strom JA, Transou CR: Cerebral arterial spasm--a controlled trial of nimodipine in patients with subarachnoid hemorrhage. N Engl J Med. 1983 Mar 17;308(11):619-24.
2. Belfort MA, Anthony J, Saade GR, Allen JC Jr: A comparison of magnesium sulfate and nimodipine for the prevention of eclampsia. N Engl J Med. 2003 Jan 23;348(4):304-11.
3. Janjua N, Mayer SA: Cerebral vasospasm after subarachnoid hemorrhage. Curr Opin Crit Care. 2003 Apr;9(2):113-9.
4. Vergouwen MD, Vermeulen M, Roos YB: Effect of nimodipine on outcome in patients with traumatic subarachnoid haemorrhage: a systematic review. Lancet Neurol. 2006 Dec;5(12):1029-32.
5. Tomassoni D, Lanari A, Silvestrelli G, Traini E, Amenta F: Nimodipine and its use in cerebrovascular disease: evidence from recent preclinical and controlled clinical studies. Clin Exp Hypertens. 2008 Nov;30(8):744-66. doi: 10.1080/10641960802580232.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12137606
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16180362
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17110283
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21869451
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22262041
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22300914
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8519001