CILOSTAZOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H27N5O2
Molecular Weight	369.4607
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCC2=C(N1)C=CC(OCCCCC3=NN=NN3C4CCCCC4)=C2

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
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=146824
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 3 61 Target ID: CHEMBL2094125 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=146824	Inhibitor 8504		0.57 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intermittent claudication 12 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=146824	Palliative		Approved 8583	CILOSTAZOL Approved Use Cilostazol tablets are indicated for the reduction of symptoms of intermittent claudication, as indicated by an increased walking distance. Launch Date 2004

C_max

Value	Dose	Co-administered	Analyte	Population
701 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31372190	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

AUC

Value	Dose	Co-administered	Analyte	Population
13724 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31372190	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31372190	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
3.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020863s011lbl.pdf			CILOSTAZOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31401	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31401
ChemicalBook	CB2362876	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2362876
eMolecules	27518122	https://www.emolecules.com/cgi-bin/more?vid=27518122
eMolecules	535670	https://www.emolecules.com/cgi-bin/more?vid=535670
MolPort	MolPort-001-758-007	https://www.molport.com/shop/molecule-link/MolPort-001-758-007
Selleck Chemicals	Cilostazol	http://www.selleckchem.com/products/Cilostazol.html
ZINC	ZINC000001552174	http://zinc15.docking.org/substances/ZINC000001552174

PubMed

Title	Date	PubMed
Effects of cilostazol on resting ankle pressures and exercise-induced ischemia in patients with intermittent claudication.	2001	11789969
Is cilostazol more effective than pentoxifylline in the treatment of symptoms of intermittent claudication?	2001 Feb	11219570
[Effects of cilostazol in patients with bradycardiac atrial fibrillation].	2001 Jan	11200653
Cilostazol: treatment of intermittent claudication.	2001 Jan	11197586
Inhibition of platelet aggregation and the release of P-selectin from platelets by cilostazol.	2001 Mar 15	11323002
Treatment of intermittent claudication with pentoxifylline and cilostazol.	2001 Mar 15	11286146
Antithrombotic therapy for prevention of pneumonia.	2001 May	11380774
Effect of cilostazol on restenosis after coronary angioplasty and stenting in comparison to conventional coronary artery stenting with ticlopidine.	2001 May	11376832
Pharmacotherapy of intermittent claudication.	2001 Nov	11825312
Interplay between inhibition of adenosine uptake and phosphodiesterase type 3 on cardiac function by cilostazol, an agent to treat intermittent claudication.	2001 Nov	11602824
Method for the quantitative analysis of cilostazol and its metabolites in human plasma using LC/MS/MS.	2001 Nov	11516916
Management of peripheral arterial disease and intermittent claudication.	2001 Nov-Dec	11757887
Differential lipogenic effects of cilostazol and pentoxifylline in patients with intermittent claudication: potential role for interleukin-6.	2001 Oct	11583728
Rapid ventricular tachycardias associated with cilostazol use.	2002	12075874
Pharmacokinetic and pharmacodynamic modeling of the antiplatelet and cardiovascular effects of cilostazol in healthy humans.	2002 Apr	11956507
Randomized comparison of cilostazol versus ticlopidine hydrochloride for antiplatelet therapy after coronary stent implantation for prevention of late restenosis.	2002 Aug	12177649
Can claudication be improved with medication?	2002 Dec	12478498
Pharmacologic therapy for peripheral arterial disease and claudication.	2002 Dec	12469066
Spontaneous recanalization of arterial occlusions: an unusual mechanism for symptomatic improvement.	2002 Dec	12469047
Thermally-prepared polymorphic forms of cilostazol.	2002 Dec	12434391
Modulation of the erythropoietin-induced proliferative pathway by cAMP in vascular smooth muscle cells.	2002 Dec	12419709
A phosphodiesterase inhibitor, cilostazol, prevents the onset of silent brain infarction in Japanese subjects with Type II diabetes.	2002 Feb	11935149
The ten most commonly asked questions about management of peripheral arterial disease.	2002 Jan-Feb	11790263
Peripheral arterial disease.	2002 Jun	12230639
Recent advances in antiplatelet agents.	2002 Mar	11945125
Neuroprotective effect of cilostazol against focal cerebral ischemia via antiapoptotic action in rats.	2002 Mar	11861782
Management of patients with intermittent claudication.	2002 Nov	12469984
Pharmacotherapy for peripheral arterial disease: emerging therapeutic options.	2002 Nov-Dec	12463615
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	12370857
New mechanism of action for cilostazol: interplay between adenosine and cilostazol in inhibiting platelet activation.	2002 Oct	12352320
[State of treatment of coronary artery disease by drug releasing stents].	2002 Sep	12378395
Debulking and stenting versus debulking only of coronary artery disease in patients treated with cilostazol (final results of ESPRIT).	2002 Sep 15	12231079
Failure of pentoxifylline or cilostazol to improve blood and plasma viscosity, fibrinogen, and erythrocyte deformability in claudication.	2002 Sep-Oct	12365857
Effects of cilostazol on serum lipid concentrations and plasma fatty acid composition in type 2 diabetic patients with peripheral vascular disease.	2003 Feb	12624709
Inhibitory action of cilostazol, a phosphodiesterase III inhibitor, on catecholamine secretion from cultured bovine adrenal chromaffin cells.	2003 Jan	12688393

Patents

Sample Use Guides

In Vivo Use Guide

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 Use Guide

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

Official Name

English

PLETAL

Preferred 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

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