Cilostazol (CED0003305)

Record Information
Version1.0
Creation Date2016-05-22 05:01:58 UTC
Update Date2026-08-20 06:25:39 UTC
Accession NumberCHEM018152
Identification
Common NameCilostazol
ClassSmall Molecule
Description
Cilostazol is an organic compound with the formula C20H27N5O2 and an average molecular weight of 369.46 g/mol. Cilostazol belongs to the quinolones and derivatives, a subclass of quinolines and derivatives within the organic compounds. It functions as an inhibitor of cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A (PDE3A) and serves as a biological antioxidant (PMC9368651). The compound is used as an antithrombotic agent within healthcare, pharmaceuticals, and veterinary products. Its health effects include treatment for kidney disease (PMC9368651), cerebrovascular disease (PMC9368651), and coronary artery disease (PMC9368651). Additionally, it has a therapeutic effect on stroke (PMC3148418). Cilostazol is found in or released from eight recorded sources. These include electrical and electronic equipment, such as discharge tubes with liquid pool cathodes, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. It is also associated with household cleaning and consumer products, specifically tobacco smoke filters, cigar cigarettes, and other smoking requisites. Recorded exposure routes for the compound include oral and conjunctival pathways.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
3,4-Dihydro-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-2(1H)-quinolinoneChEBI
6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydro-2(1H)-quinolinoneChEBI
6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydrocarbostyrilChEBI
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)-butoxy]-3,4-dihydro-1H-quinolin-2-oneChEBI
CilostazolumChEBI
PletalKegg
CilostazoleHMDB
Chemical FormulaC20H27N5O2
Average Molecular Mass369.461 g/mol
Monoisotopic Mass369.216 g/mol
CAS Registry Number73963-72-1
IUPAC Name6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one
Traditional Namecilostazol
SMILESO=C1CCC2=C(N1)C=CC(OCCCCC1=NN=NN1C1CCCCC1)=C2
InChI IdentifierInChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)
InChI KeyRRGUKTPIGVIEKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroquinolones
Alternative Parents
Substituents
  • Tetrahydroquinolone
  • Tetrahydroquinoline
  • Alkyl aryl ether
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Tetrazole
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.032 g/LALOGPS
logP3.38ALOGPS
logP3.31ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)-0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity117.13 m³·mol⁻¹ChemAxon
Polarizability41.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fal-8947000000-2a45c02fa8163a7e214eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fc3-2900000000-aeed8cd6efbb3b93af8eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dr-1698000000-05ddf5c1a046516bae11Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01t9-3920000000-86a7d65313952e9a8d3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0129000000-f672b81f1eae1e02bf26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06za-7679000000-3558d68d922f50a245e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9600000000-a29f6d9a47bb72fd9433Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0529000000-1054f4f0e8e908b32dc8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2913000000-c486550cc7475c61e6e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-5900000000-285688ae4185c24bab91Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0029000000-dcfc288c1d5ecab73a27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-9018000000-77173424302a7aea56feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0970000000-ddeea9f213a26978e589Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0109000000-55bee19f6f547c13b3b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0109000000-ad4dbc3d4880ce468bb5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1921000000-c6d1a1ca29c9d4653634Not 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
969.0Log mg/kg[540:1700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
kidney diseaseis_treatment_forNot AvailablePMC9368651
strokehas_therapeutic_effect_onNot AvailablePMC3148418
coronary artery diseaseis_treatment_forNot AvailablePMC9368651
cerebrovascular diseaseis_treatment_forNot AvailablePMC9368651
peripheral artery diseaseis_treatment_forNot AvailablePMC9368651
Exposure Sources
Source IDSourceSectorReference
273Antithrombotic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
515Discharge Tubes With Liquid Pool CathodesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)139.272
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3AQ14432HumansPredicted (SEA)8.32987
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)28.4928
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)234.326
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)199.372
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)233.392
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3BQ13370HumansPredicted (SEA)2.02408
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)186.137
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)233.937
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)90.3051
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)212.84
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)207.624
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)141.296
D(1B) dopamine receptor structureClick to view 3D structureD(1B) dopamine receptorP21918HumansPredicted (SEA)105.719
Click to view 3D structureAcetylcholinesteraseP37136Rattus norvegicusPredicted (SEA)65.4712
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)132.422
Click to view 3D structureClass I phosphodiesterase PDEB1Q6S996Leishmania majorPredicted (SEA)1.47914
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)232.925
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)354.681
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)423.422
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)313.81
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)458.688
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)273.329
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1711.75
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)232.769
Concentrations
Not Available
External Links
DrugBank IDDB01166
HMDB IDHMDB0015297
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCilostazol
Chemspider ID2652
ChEBI ID31401
PubChem Compound ID2754
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17500510
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9873372