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Cilostazol

HCID 2754
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
73963-72-1
표준 SMILES
O=C1CCc2cc(OCCCCc3nnnn3C3CCCCC3)ccc2N1
InChIKey
RRGUKTPIGVIEKM-UHFFFAOYSA-N
분자식
C20H27N5O2
평균 분자량
369.5 g/mol
단동위원소 질량
369.21647512

개요

Cilostazol is a lactam that is 3,4-dihydroquinolin-2(1H)-one in which the hydrogen at position 6 is substituted by a 4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy group. It has a role as a bronchodilator agent, a vasodilator agent, a fibrin modulating drug, an anticoagulant, a platelet aggregation inhibitor, an EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor and a neuroprotective agent. It is a lactam and a member of tetrazoles.

이름 및 식별자

우선 이름
Cilostazol
IUPAC
6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-3,4-dihydro-1H-quinolin-2-one
영어명
Cilostazol
분자식
C20H27N5O2
분자량
369.46

이름 및 동의어

cilostazol73963-72-1PletalCilostazolePletaalCilostazolumOPC-13013OPC-216-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinoneDTXSID90451323,4-Dihydro-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-2(1H)-quinolinone6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydro-2(1H)-quinolinone
이름 더 보기
CilostazoRETALOPC 21CilostalOPC 13013CILASTAZOL
6-(4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydrocarbostyrilNSC-758936CHEBI:31401N7Z035406BDTXCID70251322(1H)-Quionlinone, 6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydro-2(1H)-quinolinone, 6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydro-6-[4-(1-cyclohexyl-1h-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

데이터베이스 식별자

CAS
73963-72-1
PubChem CID
2754
DTXSID
DTXSID9045132
ChEMBL

물성

구조 계산 물성

XLogP
3.1
극성 표면적
81.9 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
5
회전 가능 결합 수
7
무거운 원자 수
27
형식 전하
0
복잡도
485

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP · 2건

2.3

2.76

Color/FormColorless needle-like crystals from methanol
Solubility · 3건

Practically insoluble in water

Freely soluble in acetic acid, chloroform, n-methyl-2-pyrrolidone, DMSO; slightly soluble in methanol, ethanol. Practically insoluble in ether. 0.1NHCl, 0.1N NaOH

3.24e-02 g/L

Human Drugs · 3건

Breastfeeding; Lactation; Fibrinolytic Agents; Platelet Aggregation Inhibitors;

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 2건

159.4-160.3 °C

160 °C

Physical DescriptionSolid
Stability/Shelf LifeStable under recommended storage conditions.
Collision Cross Section · 2건

195.62 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.

유해성 정보

FDA Requirements · 1건

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including cilostazol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides, Nitrogen oxides (NOx)
Hazard Classes and CategoriesRepr. 2 (100%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents

안전 및 보호

Fire Fighting Procedures · 2건

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage Conditions · 2건

Store Pletal tablets at 25 °C (77 °F); excursions permitted to 15-30 °C (59-86 °F).

Keep container tightly closed in a dry and well-ventilated place.

Cleanup Methods

화학 및 산업

약리 정보

ATC Code · 2건

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein Binding95-98%
Pharmacodynamics · 1건

Cilostazol reduces the symptoms of intermittent claudication, as indicated by an increased walking distance. Intermittent claudication is pain in the legs that occurs with walking and disappears with rest. The pain occurs due to reduced blood flow to the legs.

Mechanism of Action · 3건

Cilostazol and several of its metabolites are cyclic AMP (cAMP) phosphodiesterase III inhibitors (PDE III inhibitors), inhibiting phosphodiesterase activity and suppressing cAMP degradation with a resultant increase in cAMP in platelets and blood vessels, leading to inhibition of platelet aggregation and vasodilation.

Cilostazol, a phosphodiesterase 3, has been widely used in patients with arterial disease and is known to have additional beneficial effects on dyslipidemia. However, the effect of cilostazol on hepatic steatosis has not been fully elucidated. We investigated the effect of cilostazol on hepatic ABCA1 expression and hepatic steatosis in diet-induced obesity mice model. Hepatic ABCA1 expression and lipid accumulation were analyzed in HepG2 cell lines treated with cilostazol. Male C57BL/6 mice were randomly divided into three groups: (1) fed normal chow diet with vehicle; (2) fed high-fat diet (HFD) with vehicle; (3) fed HFD with cilostazol. Cilostazol (30 mg/kg) was orally administered once daily for 9 weeks. Cilostazol significantly enhanced ABCA1 expression and restored ABCA1 expression reduced by palmitate in HepG2 cells. Cilostazol treatment ameliorated lipid accumulation induced by palmitate, and this effect was diminished when ABCA1 or LRP1 was silenced by small interference RNA. After silencing of LRP1, ABCA1 expression was decreased in HepG2 cells. Cilostazol significantly enhanced hepatic ABCA1 expression and decreased hepatic fat in HFD-fed mice. Hepatic expression of cleaved caspase-3 and PARP1 was also decreased in HFD-fed mice treated with cilostazol. Cilostazol ameliorated hepatic steatosis and increased ABCA1 expression in the hepatocytes. Enhancing ABCA1 expression with cilostazol represents a potential therapeutic avenue for treatment of hepatic steatosis.

Cilostazol, a quinolinone-derivative selective phosphodiesterase (PDE) inhibitor, is a platelet-aggregation inhibitor and arterial vasodilator. Although the mechanism of action of cilostazol has not been fully elucidated, the drug appears to inhibit activation of cellular PDE type III (PDE III), resulting in suppressed degradation, and thus increased concentrations, of cyclic adenosine-3',5'-monophosphate (cAMP) in platelets and blood vessels. Increased cAMP concentrations are thought to result in arterial vasodilation and inhibition of platelet aggregation.

관련 반응

17건
반응 기록 만들기
HRID 697047 반응식
HRID 697047반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 748608 반응식
HRID 748608생성물로uspto-grants-2008_07
HRID 748609 반응식
HRID 748609생성물로uspto-grants-2008_07
HRID 987186 반응식
HRID 987186생성물로uspto-grants-2003_10
HRID 987187 반응식
HRID 987187생성물로uspto-grants-2003_10
HRID 1170049 반응식
HRID 1170049생성물로uspto-grants-2010_11
HRID 1170050 반응식
HRID 1170050생성물로uspto-grants-2010_11
HRID 1227103 반응식
HRID 1227103반응물로Training data from https://doi.org/10.1039/C8SC04228D (5/10)
1 / 3 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
CHEMBL799
ChEBI
CHEBI:31401
UNII
N7Z035406B
EC Number
689-122-9
Nikkaji
J23.223H

199.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
159 · 159-160°C
끓는 점
499.57 °C · 499.57°C (rough estimate)
밀도
1.1832 · 1.1832 (rough estimate)
굴절률
1.76 · 1.7600 (estimate)
저장 조건
Inert atmosphere,Room Temperature
용해도
18 mg/mL, · DMSO: 18mg/mL, 가용성
물리적 상태
고체
산도 계수 (pKa)
14.22 · 14.22±0.20(Predicted)
색상
회백색
Merck
14 · 14,2277
안정성
-20 °C에서 · -20°C에서 DMSO에 최대 2개월 동안 보관 가능
주요 응용
의약품(소분자)
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)
InChIKey
RRGUKTPIGVIEKM-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(OCCCCC3N(C4CCCCC4)N=NN=3)C=C2)CCC1=O

화학적 성질

Colourless Needles

· 1건

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas; Environmental precautions: Do not let product enter drains; Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

Disposal Methods · 2건

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Preventive Measures · 4건

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

Appropriate engineering controls: General industrial hygiene practice.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Personal Protective Equipment (PPE) · 4건

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

독성 정보

Interactions · 5건

Pharmacokinetic interaction (increased plasma concentrations of active metabolite 3,4-dehydro-cilostazol) with CYP2C19 inhibitors, including omeprazole; use with caution and consider reduced dosage.

Potential pharmacokinetic interaction (increased plasma lovastatin concentrations and decreased plasma cilostazol concentration) with lovastatin, a substrate for CYP3A4, although unlikely to be clinically important.

Pharmacokinetic interaction (increased plasma cilostazol concentrations); use with caution and consider reduced dosage. Potential pharmacokinetic interaction (increased plasma cilostazol concentrations, decreased clearance) with other inhibitors of CYP3A4 isoenzyme, including, but not limited to, certain azole antifungals (e.g., fluconazole, itraconazole, ketoconazole, miconazole), certain macrolide antibiotics (e.g., erythromycin or clarithromycin but not azithromycin), certain selective serotonin-reuptake inhibitors (e.g., fluoxetine, fluvoxamine, nefazodone, sertraline), certain antiretroviral agents (e.g., indinavir), metronidazole, diltiazem, and danazol.

Potentially additive antiplatelet effects with clopidogrel and cilostazol. Caution is advised and bleeding times should be monitored during such concomitant therapy. Pharmacokinetic interaction unlikely.

For more Interactions (Complete) data for Cilostazol (10 total), please visit the HSDB record page.

Hepatotoxicity · 1건

In publications of the multiple, large prospective trials of cilostazol therapy, rates of serum ALT elevations during therapy were not provided. Furthermore, there were no reported instances of clinically apparent acute liver injury. Since its approval and wide scale use, there have been no published reports of hepatotoxicity attributed to cilostazol. Nevertheless, the current product label mentions that instances of serum enzyme elevations and hepatitis have been reported to the sponsor. The time of onset, clinical pattern and course of liver test abnormalities during cilostazol therapy have not been reported.

Adverse Effects · 1건

Cilostazol is a generally well-tolerated oral medication. Common side effects of cilostazol therapy reportedly include headache (34%), diarrhea (19%), and palpitations (10%). A slight elevation in heart rate of 5 to 7 beats/min may also occur with the administration of cilostazol. These side effects are mild to moderate in intensity, transient, or alleviated with symptomatic treatment and seldom demand treatment withdrawal. Cilostazol may induce tachycardia, tachyarrhythmia, and hypotension. Postmarketing research has shown cilostazol to induce thrombocytopenia or leukopenia, progressing to agranulocytosis when drug administration is not immediately discontinued. Agranulocytosis is reversible with immediate discontinuation of the drug.

Toxicity Summary · 2건

IDENTIFICATION AND USE: Cilostazol forms colorless, needle-like crystals. As the oral drug Pletal, it is indicated for the reduction of symptoms of intermittent claudication. HUMAN EXPOSURE AND TOXICITY: The signs and symptoms of an acute overdose may include severe headache, diarrhea, hypotension, tachycardia, and possibly cardiac arrhythmias. ANIMAL STUDIES: No cardiovascular lesions were seen in rats following 5 or 13 weeks of administration of cilostazol at doses up to 1500 mg/kg/day. At this dose, systemic exposures (AUCs) to unbound cilostazol were only about 1.5 and 5 times (male and female rats, respectively) the exposure seen in humans at the maximum recommended human dose (MRHD). Repeated oral administration of cilostazol to dogs produced cardiovascular lesions that included endocardial hemorrhage, hemosiderin deposition and fibrosis in the left ventricle, hemorrhage in the right atrial wall, hemorrhage and necrosis of the smooth muscle in the wall of the coronary artery, intimal thickening of the coronary artery, and coronary arteritis and periarteritis. At the lowest dose associated with cardiovascular lesions in the 52-week study, AUC to unbound cilostazol was less than that seen in humans at the MRHD of 100 mg twice daily. In a rat developmental toxicity study, oral administration of 1000 mg cilostazol/kg/day was associated with decreased fetal weights, and increased incidences of cardiovascular, renal, and skeletal anomalies (ventricular septal, aortic arch and subclavian artery abnormalities, renal pelvic dilation, 14th rib, and retarded ossification). Cilostazol tested negative in bacterial gene mutation, bacterial DNA repair, mammalian cell gene mutation, and mouse in vivo bone marrow chromosomal aberration assays. It was, however, associated with a significant increase in chromosomal aberrations in the in vitro Chinese Hamster Ovary Cell assay. Dietary administration of cilostazol to rats and mice for up to 104 weeks revealed no evidence of carcinogenic potential. The maximum doses administered in both rat and mouse studies were, on a systemic exposure basis, less than the human exposure at the MRHD of the drug.

The oral lethal dose of cilostazol is over 5 g/kg in rats and mice and more than 2 g/kg in dogs. There is a lack of data on acute overdosage with cilostazol in humans. The signs and symptoms of an acute cilostazol overdose can present as a severe headache, diarrhea, hypotension, tachycardia, and possibly cardiac arrhythmia. In an overdose, patients require careful observation and supportive treatment. Cilostazol is highly protein-bound and unlikely to be efficiently removed by hemodialysis or peritoneal dialysis. Emptying the stomach by gastric lavage may be appropriate if needed.

Ongoing Test Status · 1건

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of December 17, 2015: http://actor.epa.gov/dashboard/]

Human Toxicity Excerpts · 5건

/SIGNS AND SYMPTOMS/ Cilostazol may induce tachycardia, palpitation, tachyarrhythmia or hypotension. The increase in heart rate associated with cilostazol is approximately 5 to 7 bpm. Patients with a history of ischemic heart disease may be at risk for exacerbations of angina pectoris or myocardial infarction.

/SIGNS AND SYMPTOMS/ The signs and symptoms of an acute overdose can be anticipated to be those of excessive pharmacologic effect: severe headache, diarrhea, hypotension, tachycardia, and possibly cardiac arrhythmias.

/CASE REPORTS/ Cilostazol, a phosphodiesterase III inhibitor, is known to increase the heart rate; however, its effects on glucose metabolism remain unclear. We observed that the blood glucose level varied in parallel with the heart rate immediately after starting or stopping cilostazol therapy in three patients with type 2 diabetes. This finding indicates that cilostazol induces hyperglycemia and tachycardia in a portion of diabetic patients, presumably via similar pharmacological effects on different organs. Much more attention should be paid to the possible effects of cilostazol on glycemic control, including taking into consideration the risk-benefit ratio of cilostazol use and individual circumstances.

/ALTERNATIVE and IN VITRO TESTS/ Cilostazol, a selective phosphodiesterase 3 (PDE3) inhibitor, is known as an anti-platelet drug and acts directly on platelets. Cilostazol has been shown to exhibit vascular protection in ischemic diseases. Although vascular endothelium-derived prostaglandin I2 (PGI2) plays an important role in vascular protection, it is unknown whether cilostazol directly stimulates PGI2 synthesis in endothelial cells. Here, we elucidate the mechanism of cilostazol-induced PGI2 stimulation in endothelial cells. Human aortic endothelial cells (HAECs) were stimulated with cilostazol and PGI2 accumulation in the culture media was measured. Cilostazol increased PGI2 synthesis via the arachidonic acid pathway. Cilostazol-induced intracellular calcium also promoted PGI2 synthesis via the inositol 1,4,5-trisphosphate receptor. Using RNAi, silencing of PDE3B abolished the induction effect of cilostazol on PGI2 synthesis and intracellular cAMP accumulation. Inhibition of the exchange protein, which was directly activated by cyclic AMP 1 (Epac-1) and its downstream signal the Ras-like small GTPase (Rap-1), abolished cilostazol-induced PGI2 synthesis, but this did not take place via protein kinase A (PKA). Inhibition of downstream signaling, such as mitogen-activated protein kinase (MAPK), phosphoinositide 3-kinase (PI3K) gamma, and phospholipase C (PLC) e, suppressed cilostazol-induced PGI2 synthesis. The PDE3/Epac-1/Rap-1 signaling pathway plays an important role in cilostazol-induced PGI2 synthesis. Namely, stimulation of HAECs with cilostazol induces intracellular calcium elevation via the Rap-1/PLCe/IP3 pathway, along with MAPK activation via direct activation by Epac-1/Rap-1 and indirect activation by Epac-1/Rap-1/PI3Kgamma, resulting in synergistically induced PGI2 synthesis.

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Cilostazol

Ambiguous-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 5건

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Cardiovascular lesions were ... not observed in monkeys after oral administration of cilostazol for 13 weeks at doses up to 1800 mg/kg/day. While this dose of cilostazol produced pharmacologic effects in monkeys, plasma cilostazol levels were less than those seen in humans given the MRHD, and those seen in dogs given doses associated with cardiovascular lesions.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ No cardiovascular lesions were seen in rats following 5 or 13 weeks of administration of cilostazol at doses up to 1500 mg/kg/day. At this dose, systemic exposures (AUCs) to unbound cilostazol were only about 1.5 and 5 times (male and female rats, respectively) the exposure seen in humans at the maximum recommended human dose (MRHD).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Cilostazol, a selective type III phosphodiesterase inhibitor, has antiplatelet and vasodilating effects. In this study, the effects of cilostazol on lipid metabolism and lipoprotein lipase (LPL) activity were studied in rats. Cilostazol was administered orally at doses of 30 or 100 mg/kg twice a day for 1-2 weeks to rats. Cilostazol decreased the serum triglyceride level in normolipidemic rats. The serum triglyceride level was reduced and HDL cholesterol level was increased by cilostazol in streptozotocin (STZ)-induced diabetic rats. The disappearance of exogenous triglyceride was accelerated by cilostazol in normolipidemic rats. Cilostazol increased post-heparin plasma LPL activity but had no effect on hepatic triglyceride lipase activity in STZ-induced diabetic rats. Cilostazol also increased LPL activity in the heart in STZ-induced diabetic rats. These findings suggest that an increase in LPL activity is responsible for the serum triglyceride lowering and HDL cholesterol elevating effects of cilostazol in rats.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Repeated oral administration of cilostazol to dogs (30 or more mg/kg/day for 52 weeks, 150 or more mg/kg/day for 13 weeks, and 450 mg/kg/day for 2 weeks), produced cardiovascular lesions that included endocardial hemorrhage, hemosiderin deposition and fibrosis in the left ventricle, hemorrhage in the right atrial wall, hemorrhage and necrosis of the smooth muscle in the wall of the coronary artery, intimal thickening of the coronary artery, and coronary arteritis and periarteritis. At the lowest dose associated with cardiovascular lesions in the 52-week study, systemic exposure (AUC) to unbound cilostazol was less than that seen in humans at the maximum recommended human dose (MRHD) of 100 mg twice daily. Similar lesions have been reported in dogs following the administration of other positive inotropic agents (including PDE III inhibitors) and/or vasodilating agents.

For more Non-Human Toxicity Excerpts (Complete) data for Cilostazol (15 total), please visit the HSDB record page.

Populations at Special Risk · 2건

WARNING: CONTRAINDICATED IN HEART FAILURE PATIENTS. Pletal is contraindicated in patients with heart failure of any severity. Cilostazol and several of its metabolites are inhibitors of phosphodiesterase III. Several drugs with this pharmacologic effect have caused decreased survival compared to placebo in patients with class III-IV heart failure.

Cilostazol may induce tachycardia, palpitation, tachyarrhythmia or hypotension. The increase in heart rate associated with cilostazol is approximately 5 to 7 bpm. Patients with a history of ischemic heart disease may be at risk for exacerbations of angina pectoris or myocardial infarction.

Antidote and Emergency Treatment · 3건

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Non-Human Toxicity Values · 3건

LD50 Dog oral > 2 g/kg

LD50 Rat oral > 5 g/kg

LD50 Mouse oral > 5 g/kg

규제 정보

FDA Requirements · 1건

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including cilostazol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

안전 데이터

wgk
2
rtecs
VC8277500
독성
LD50 in mice, rats (mg/kg): >2000, >2000 i.p.; >5000, >5000 orally (Nomura)
HS 번호
29339900
hazard_code
Xi
Hazard Classifications
Repr. 2
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
73963-72-1(Hazardous Substances Data)
Biological Half-Life · 2건

11-13 hours.

Cilostazol and its active metabolites have apparent elimination half-lives of about 11-13 hours.

Metabolism/Metabolites · 6건

Hepatic. Cilostazol is extensively metabolized by hepatic cytochrome P-450 enzymes, mainly 3A4, and, to a lesser extent, 2C19, with metabolites largely excreted in urine. Two metabolites are active, with one metabolite appearing to account for at least 50% of the pharmacologic (PDE III inhibition) activity after administration of cilostazol.

Following oral administration of 100 mg radiolabeled cilostazol, 56% of the total analytes in plasma was cilostazol, 15% was 3,4-dehydro-cilostazol (4-7 times as active as cilostazol), and 4% was 4'-trans-hydroxy-cilostazol (20% as active as cilostazol).

Cilostazol is eliminated predominantly by metabolism and subsequent urinary excretion of metabolites. Based on in vitro studies, the primary isoenzymes involved in cilostazol's metabolism are CYP3A4 and, to a lesser extent, CYP2C19. The enzyme responsible for metabolism of 3,4-dehydro-cilostazol, the most active of the metabolites, is unknown.

Cilostazol is extensively metabolized by hepatic cytochrome P-450 enzymes, mainly 3A4, and, to a lesser extent, 2C19, with metabolites largely excreted in urine. Two metabolites are active, with one metabolite appearing to account for at least 50% of the pharmacologic (PDE III inhibition) activity after administration of Pletal.

The pharmacokinetics of cilostazol was investigated after oral and intravenous administration in both male and female rats. After oral administration, area under serum concentration-time curve (AUC) was about 35-fold higher in female rats than in male rats, and absolute bioavailability was about 5.8-fold higher in female rats than in male rats. Total body clearance (CL(total)) for female rats was around one-sixth of that for male rats. In vivo hepatic clearance (CL(h)) calculated based on isolated liver perfusion studies was even higher than or around 90% of the in vivo CL(total) of cilostazol for female and male rats, respectively, indicating that cilostazol is mainly eliminated by the liver in both male and female rats. In vitro metabolism studies utilizing hepatic microsomes and recombinant cytochrome (CYP) isoforms clearly indicated that major metabolites of cilostazol were generated extensively with hepatic microsomes of male rats and that male-predominant CYP3A2 and male-specific CYP2C11 were mainly responsible for the hepatic metabolism of cilostazol. Therefore, the great sex differences in the pharmacokinetics of cilostazol were mainly attributed to the large difference in hepatic metabolism. Our experimental results also suggested that the substantial metabolism of cilostazol in the small intestine and its possible saturation would be responsible for dose-dependent bioavailability in both male and female rats.

The primary route of elimination was via the urine (74%), with the remainder excreted in feces (20%). No measurable amount of unchanged cilostazol was excreted in the urine, and less than 2% of the dose was excreted as 3,4-dehydro-cilostazol. About 30% of the dose was excreted in urine as 4'-trans-hydroxy-cilostazol. The remainder was excreted as other metabolites, none of which exceeded 5%. There was no evidence of induction of /microsomal enzymes/.

FDA Pharmacological Classification · 6건

N7Z035406B

CILOSTAZOL

Established Pharmacologic Class [EPC] - Phosphodiesterase 3 Inhibitor

Mechanisms of Action [MoA] - Phosphodiesterase 3 Inhibitors

Cilostazol is a Phosphodiesterase 3 Inhibitor. The mechanism of action of cilostazol is as a Phosphodiesterase 3 Inhibitor.

CILOSTAZOL

MeSH Pharmacological Classification · 6건

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Drugs used to cause dilation of the blood vessels.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Compounds that specifically inhibit PHOSPHODIESTERASE 3.

Absorption, Distribution and Excretion · 6건

Cilostazol is absorbed after oral administration. A high fat meal increases absorption, with an approximately 90% increase in Cmax and a 25% increase in AUC. Absolute bioavailability is not known.

Cilostazol is extensively metabolized by hepatic cytochrome P-450 enzymes, mainly 3A4, and, to a lesser extent, 2C19, with metabolites largely excreted in urine. Cilostazol is eliminated predominately by metabolism and subsequent urinary excretion of metabolites. The primary route of elimination was via the urine (74%), with the remainder excreted in feces (20%). No measurable amount of unchanged cilostazol was excreted in the urine, and less than 2% of the dose was excreted as 3,4-dehydro-cilostazol. About 30% of the dose was excreted in urine as 4'-trans-hydroxy-cilostazol.

/MILK/ Transfer of cilostazol into milk has been reported in rats.

Following oral administration of a single 100-mg dose of cilostazol with a high-fat meal, peak plasma cilostazol concentrations and area under the plasma concentration-time curve (AUC) increased by approximately 90 and 25%, respectively.

Pletal is absorbed after oral administration. A high fat meal increases absorption, with an approximately 90% increase in Cmax and a 25% increase in AUC. Absolute bioavailability is not known.

The primary route of elimination was via the urine (74%), with the remainder excreted in feces (20%). No measurable amount of unchanged cilostazol was excreted in the urine, and less than 2% of the dose was excreted as 3,4-dehydro-cilostazol. About 30% of the dose was excreted in urine as 4'-trans-hydroxy-cilostazol. The remainder was excreted as other metabolites, none of which exceeded 5%. There was no evidence of induction of /microsomal enzymes/.

Cellular LocationsMembrane
Metabolite PathwaysCilostazol Action Pathway

용도 및 제조

Uses · 2건

MEDICATION

Use (kg; approx.) in Germany (2009): >1000

Methods of ManufacturingPreparation: Belgium patent 878548; T. Nishi, K. Nakagawa, United States of America patent 4277479 (1979, 1981 both to Otsuka).
Formulations/PreparationsTable: Cilostazol Preparations [Table#8325]
응용 분야 · 3건

개요Cilostazol is a platelet aggregation inhibitor with cerebral vasodilating activity, indicated for use in stroke and myocardial infarction. In patients with cerebral thrombosis, transient ischemia and cerebral arteriosclerosis, cilostazol significantly inhibits ADP-, collagenand epinephrine-induced platelet aggregation. Side effects include headache and tachycardia.

용도A potent phosphodiesterase III A (PDE3A) inhibitor (IC50=0.2uM) and inhibitor of adenosine uptake. Has antimitogeni, antithrombotic, vasodilatory and cardiotonic properties in vivo. Also affects lipid levels in vivo

일반 설명Cilostazol is a potent cyclic nucleotide phosphodiesterase inhibitor. It is mainly used as antiplatelet agent.

상·하류 제품 정보

상류 원료

Pentanamide황산 나트륨1H-테트라졸3,4-DIHYDROQUINOLIN-2(1H)-ONE물인 펜타염화물2(1H)-Quinolinone, 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-, sulfate (1:1)6-Hydroxy-2(1H)-3,4-dihydroquinolinone2(1H)-Quinolinone, 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-, ethanedioate (1:1)2(1H)-Quinolinone, 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-, (2Z)-2-butenedioate (1:1)

하류 제품

Cilostazol Related Compound C (50 mg) (1-(4-(5-Cyclohexyl-1H-tetrazol-1-yl)butyl)-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one)

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추가 설명

정의ChEBI: A lactam that is 3,4-dihydroquinolin-2(1H)-one in which the hydrogen at position 6 is substiuted by a 4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy group.

For more Human Toxicity Excerpts (Complete) data for Cilostazol (8 total), please visit the HSDB record page.