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=CC(OCCCCC3=NN=NN3C4CCCCC4)=CC=C2N1

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

Molecular Formula	C20H27N5O2
Molecular Weight	369.4607
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 60 Target ID: CHEMBL2094125 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=146824	Inhibitor 8297		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 8429	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
9.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21718207	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

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
17.5 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21718207	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

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
58.7% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21718207	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% 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
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
eMolecules	27518122	https://www.emolecules.com/cgi-bin/more?vid=27518122
eMolecules	535670	https://www.emolecules.com/cgi-bin/more?vid=535670

PubMed

Title	Date	PubMed
Decrease in carotid intima media thickness after 1 year of cilostazol treatment in patients with type 2 diabetes mellitus.	2001 Apr	11182215
Estimation of anti-platelet drugs on human platelet aggregation with a novel whole blood aggregometer by a screen filtration pressure method.	2001 Aug	11498527
Determination of cilostazol and its metabolites in human urine by high performance liquid chromatography.	2001 Jan	11199217
The effect of cilostazol on glucose tolerance and insulin resistance in a rat model of non-insulin dependent diabetes mellitus.	2001 Jun	11590907
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
Cilostazol for prevention of thrombosis and restenosis after intracoronary stenting.	2001 Sep	11573862
Antiplatelet agent cilostazol potentiates adipocyte differentiation of 3T3-L1 cells.	2001 Sep	11500170
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
Inhibition of lipopolysaccharide-induced apoptosis by cilostazol in human umbilical vein endothelial cells.	2002 Feb	11805237
Cilostazol.	2002 Feb 1	11862634
Cilostazol in intermittent claudication.	2002 Jan 1	11813475
Treating peripheral arterial disease in patients with diabetes.	2002 Mar	12180355
Evidence-based symptom relief of intermittent claudication: efficacy and safety of cilostazol.	2002 Mar	12180354
Effects of a single oral dose of cilostazol on epicardial coronary arteries and hemodynamics in humans.	2002 Mar	11922271
Measuring treatment effects of cilostazol on clinical trial endpoints in patients with intermittent claudication.	2002 Mar	11892686
Effect of cilostazol in patients with intermittent claudication: a randomized, double-blind, placebo-controlled study.	2002 Mar-Apr	11951094
Management of patients with intermittent claudication.	2002 Nov	12469984
Pharmacotherapy for peripheral arterial disease: emerging therapeutic options.	2002 Nov-Dec	12463615
Effects of cilostazol, a selective cyclic AMP phosphodiesterase inhibitor on isolated rabbit spinal arterioles.	2002 Oct	12533252
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
Cilostazol: an "intermittent claudication" remedy for the management of third-degree AV block.	2003 Apr	12684279
A paclitaxel-eluting stent for the prevention of coronary restenosis.	2003 Apr 17	12700373
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:38:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:38:29 GMT 2023`
Record UNII	N7Z035406B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CILOSTAZOL

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