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Details

Stereochemistry ACHIRAL
Molecular Formula C20H27N5O2
Molecular Weight 369.4614
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CILOSTAZOL

SMILES

C1CCC(CC1)n2c(CCCCOc3ccc4c(CCC(=O)N4)c3)nnn2

InChI

InChIKey=RRGUKTPIGVIEKM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11830753

Cilostazol is a PDE3 inhibitor which is used for the treatment of intermittent claudication. The drug positively affects the platelet aggregation and may be used off-label as a measure to prevent coronary thrombosis/restenosis and stroke recurrence.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.57 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CILOSTAZOL

Approved Use

Cilostazol tablets are indicated for the reduction of symptoms of intermittent claudication, as indicated by an increased walking distance.

Launch Date

1.10108161E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
701 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9.2 ng/mL
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL serum
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
13724 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
17.5 ng × h/mL
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL serum
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
58.7%
0.5 mg/kg single, oral
dose: 0.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CILOSTAZOL serum
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.5%
CILOSTAZOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Potent effects of novel anti-platelet aggregatory cilostamide analogues on recombinant cyclic nucleotide phosphodiesterase isozyme activity.
2000 Feb 15
Cyclic AMP inhibited proliferation of human aortic vascular smooth muscle cells, accompanied by induction of p53 and p21.
2000 Jan
Effect of cilostazol on endothelial cell denudation and proliferation in canine vein grafts.
2001
New treatment options in intermittent claudication: the US experience.
2001 Apr
A new treatment for peripheral arterial disease.
2001 Apr
Is cilostazol more effective than pentoxifylline in the treatment of symptoms of intermittent claudication?
2001 Feb
Cilostazol suppresses intimal formation in dog grafted veins with reduction of angiotensin II-forming enzymes.
2001 Jan 12
Comparative effects of cilostazol and other therapies for intermittent claudication.
2001 Jun 28
Intermittent claudication: effective medical management of a common circulatory problem.
2001 Jun 28
Treatment of intermittent claudication with pentoxifylline and cilostazol.
2001 Mar 15
Three cases of digital ischemia successfully treated with cilostazol.
2001 Nov
Pharmacotherapy of intermittent claudication.
2001 Nov
Interplay between inhibition of adenosine uptake and phosphodiesterase type 3 on cardiac function by cilostazol, an agent to treat intermittent claudication.
2001 Nov
Management of peripheral arterial disease and intermittent claudication.
2001 Nov-Dec
Systemic atherosclerosis risk and the mandate for intervention in atherosclerotic peripheral arterial disease.
2001 Oct 11
Cilostazol for prevention of thrombosis and restenosis after intracoronary stenting.
2001 Sep
Antiplatelet agent cilostazol potentiates adipocyte differentiation of 3T3-L1 cells.
2001 Sep
Pharmacologic treatment for intermittent claudication.
2002
Cilostazol treatment of claudication in diabetic patients.
2002
Thermally-prepared polymorphic forms of cilostazol.
2002 Dec
Modulation of the erythropoietin-induced proliferative pathway by cAMP in vascular smooth muscle cells.
2002 Dec
[Etiology, pathogenesis and management of senile inflammatory pulmonary diseases].
2002 Jan
Current medical therapies for patients with peripheral arterial disease: a critical review.
2002 Jan
Potential emerging therapeutic strategies to prevent restenosis in the peripheral vasculature.
2002 Jul
Peripheral arterial disease.
2002 Jun
[Antiproliferative coated stents and intracoronary brachytherapy: common traits and differences].
2002 Jun
[Effect of cilostazol on adhesion molecules of STZ-induced diabetic rats].
2002 Jun 10
Treating peripheral arterial disease in patients with diabetes.
2002 Mar
Recent advances in antiplatelet agents.
2002 Mar
Measuring treatment effects of cilostazol on clinical trial endpoints in patients with intermittent claudication.
2002 Mar
Effect of cilostazol in patients with intermittent claudication: a randomized, double-blind, placebo-controlled study.
2002 Mar-Apr
Management of patients with intermittent claudication.
2002 Nov
Pharmacotherapy for peripheral arterial disease: emerging therapeutic options.
2002 Nov-Dec
Cilostazol, a potent phosphodiesterase type III inhibitor, selectively increases antiatherogenic high-density lipoprotein subclass LpA-I and improves postprandial lipemia in patients with type 2 diabetes mellitus.
2002 Oct
Comparison of the effects of cilostazol and milrinone on cAMP-PDE activity, intracellular cAMP and calcium in the heart.
2002 Sep
[State of treatment of coronary artery disease by drug releasing stents].
2002 Sep
Identification of interaction sites of cyclic nucleotide phosphodiesterase type 3A with milrinone and cilostazol using molecular modeling and site-directed mutagenesis.
2002 Sep
Debulking and stenting versus debulking only of coronary artery disease in patients treated with cilostazol (final results of ESPRIT).
2002 Sep 15
Failure of pentoxifylline or cilostazol to improve blood and plasma viscosity, fibrinogen, and erythrocyte deformability in claudication.
2002 Sep-Oct
Pharmacotherapy as adjunctive treatment for serious foot wounds in the patient with diabetes: a case study.
2003 Apr
Effect of cilostazol on the ventricular escape rate and neurohumoral factors in patients with third-degree atrioventricular block.
2003 Apr
Cilostazol: an "intermittent claudication" remedy for the management of third-degree AV block.
2003 Apr
A paclitaxel-eluting stent for the prevention of coronary restenosis.
2003 Apr 17
Effects of cilostazol on serum lipid concentrations and plasma fatty acid composition in type 2 diabetic patients with peripheral vascular disease.
2003 Feb
Inhibitory action of cilostazol, a phosphodiesterase III inhibitor, on catecholamine secretion from cultured bovine adrenal chromaffin cells.
2003 Jan
Adenosine receptors and phosphodiesterase inhibitors stimulate Cl- secretion in Calu-3 cells.
2003 Sep
Patents

Sample Use Guides

The recommended dosage of cilostazol tablets is 100 mg b.i.d. taken at least half an hour before or 2 hours after breakfast and dinner.
Route of Administration: Oral
In vitro assay of anti-platelet effects of cilostazol against collagen-induced aggregation using Multiplate produced a graded dose-dependent inhibition curve with IC50 value of 75.4 ± 2.4 uM while it showed a highly sensitive and all-or-none type inhibition response from 25 uM in PFA-100.
Name Type Language
CILOSTAZOL
INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
6-(4-(1-CYCLOHEXYL-1H-TETRAZOL-5-YL)BUTOXY)-3,4-DIHYDROCARBOSTYRIL
Common Name English
CILOSTAZOL [MI]
Common Name English
OPC-21
Code English
2(1H)-QUINOLINONE, 6-(4-(1-CYCLOHEXYL-1H-TETRAZOL-5-YL)BUTOXY)-3,4-DIHYDRO-
Systematic Name English
CILOSTAZOL [USP-RS]
Common Name English
NSC-758936
Code English
CILOSTAZOL [JAN]
Common Name English
CILOSTAZOL [WHO-DD]
Common Name English
OPC-13013
Code English
CILOSTAZOL [VANDF]
Common Name English
CILOSTAZOL [USAN]
Common Name English
PLETAL
Brand Name English
CILOSTAZOL [MART.]
Common Name English
CILOSTAZOL [USP MONOGRAPH]
Common Name English
CILOSTAZOL [INN]
Common Name English
CILOSTAZOL [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
NCI_THESAURUS C1327
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
WHO-ATC B01AC23
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
LIVERTOX 208
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
WHO-VATC QB01AC23
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
NDF-RT N0000175598
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
NDF-RT N0000175086
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
Code System Code Type Description
MESH
C045645
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
CAS
73963-72-1
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
NCI_THESAURUS
C1051
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
FDA UNII
N7Z035406B
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
IUPHAR
7148
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
MERCK INDEX
M3550
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1134153
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY USP-RS
PUBCHEM
2754
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
DRUG BANK
DB01166
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
WIKIPEDIA
CILOSTAZOL
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
DRUG CENTRAL
644
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
LACTMED
Cilostazol
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
HSDB
8312
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
EVMPD
SUB06273MIG
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
RXCUI
21107
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY RxNorm
EPA CompTox
73963-72-1
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
INN
5680
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL799
Created by admin on Fri Jun 25 21:04:32 UTC 2021 , Edited by admin on Fri Jun 25 21:04:32 UTC 2021
PRIMARY