CILOSTAZOL

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Search structure


Trade Names	CILOSTAZOL PLETAL
Synonyms	Cilostazol NSC-758936 OPC-13013 OPC-21 Pletal
Status
Molecule Category	UNKNOWN
ATC	B01AC23
UNII	N7Z035406B
EPA CompTox	DTXSID9045132


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RRGUKTPIGVIEKM-UHFFFAOYSA-N
Smiles	O=C1CCc2cc(OCCCCc3nnnn3C3CCCCC3)ccc2N1
InChI	InChI=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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H27N5O2
Molecular Weight	369.47
AlogP	3.46
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	7.0
Polar Surface Area	81.93
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Phosphodiesterase 3A inhibitor	INHIBITOR	DailyMed


Protein: Phosphodiesterase 3A Description: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A Organism : Homo sapiens Q14432 ENSG00000172572

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3A	-	190-840	-	-	-
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3B	-	190-840	-	-	-
Ion channel Voltage-gated ion channel Voltage-gated calcium channel	-	91200	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	207
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	16600	-	-	-

Assay Description	Organism	Bioactivity	Reference
In vivo anti-thrombotic activity was evaluated by the inhibition of pulmonary thromboembolism model in mice at a dose of 30 mg/kg (p.o.)	Mus musculus	82.0 %
Inhibition of low Km cAMP phosphodiesterase PDE III of human platelets	Homo sapiens	190.0 nM
In vivo anti-hyperplastic activity was evaluated by the inhibition of balloon injury model in rats at a dose of 30 mg/kg (p.o.)	Rattus norvegicus	12.0 %
Inhibition of human platelet PDE3	Homo sapiens	280.0 nM
Inhibition of human recombinant PDE3 catalytic domain expressed in baculovirus-infected insect Sf9 cells by modified two-step method	Homo sapiens	840.0 nM
DRUGMATRIX: Phosphodiesterase PDE3 enzyme inhibition (substrate: [3H]cAMP + cAMP)	Homo sapiens	271.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	207.15 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	98.73 %
Inhibition of PDE3 (unknown origin)	Homo sapiens	200.0 nM
Inhibition of PDE3 (unknown origin)	Homo sapiens	200.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	30.37 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	12.13 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.27 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.22 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.22 %
Inhibition of human PDE3A expressed in Sf9 cells using cAMP as substrate after 3 hrs by IMAP TR-FRET assay	Homo sapiens	3.89 nM

Cross References

Resources	Reference
ChEBI	31401
ChEMBL	CHEMBL799
DrugBank	DB01166
DrugCentral	644
FDA SRS	N7Z035406B
Human Metabolome Database	HMDB0015297
Guide to Pharmacology	7148
PharmGKB	PA164746334
PubChem	2754
SureChEMBL	SCHEMBL16128
ZINC	ZINC000001552174

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).