Cilostazol

1. Introduction of Cilostazol
Cilostazol is one kind of white crystalline powder or off-white solid. The IUPAC Name of it is 6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-3,4-dihydro-1H-quinolin-2-one. The Solubility of it is DMSO: 18 mg/mL, soluble. Besides, it belongs to Intermediates & Fine Chemicals;Isotope Labeled Compounds;Pharmaceuticals.

Its Classification Code is Anti-Asthmatic Agents; Antithrombotic; Autonomic Agents; Bronchodilator Agents; Cardiovascular Agents; Central Nervous System Agents; Drug / Therapeutic Agent; Enzyme Inhibitors; Fibrin Modulating Agents; Fibrinolytic Agents; Hematologic Agents; Human Data; Inhibitor [platelet]; Neuroprotective Agents; Peripheral Nervous System Agents; Phosphodiesterase 3 Inhibitors; Phosphodiesterase Inhibitors; Platelet Aggregation Inhibitors; Protective Agents; Reproductive Effect; Respiratory System Agents; Vasodilator; Vasodilator Agents.

2. Properties of Cilostazol
Physical properties about Cilostazol are:
(1)Empirical Formula: C₂₀H₂₇N₅O₂; (2)H bond acceptors: 7; (3)H bond donors: 1; (4)Freely Rotating Bonds: 7; (5)Polar Surface Area: 73.14 Å²; (6)Index of Refraction: 1.675; (7)Molar Refractivity: 102.93 cm³; (8)Molar Volume: 273.7 cm³; (9)Surface Tension: 54.9 dyne/cm; (10)Density: 1.34 g/cm³; (11)Flash Point: 355.8 °C; (12)Enthalpy of Vaporization: 97.74 kJ/mol; (13)Boiling Point: 664.7 °C at 760 mmHg; (14)Vapour Pressure: 1.56E-17 mmHg at 25°C; (15)Melting point: 159-160°C.

3. Structure Descriptors of Cilostazol
(1)InChI: InChI=1/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)
(2)Smiles: n1(c(nnn1)CCCCOc1cc2c(NC(=O)CC2)cc1)C1CCCCC1
(3)InChIKey: InChIKey=RRGUKTPIGVIEKM-UHFFFAOYSA-N

4. Toxicity of Cilostazol

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 2gm/kg (2000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
man	TDLo	oral	1248ug/kg (1.248mg/kg)	BEHAVIORAL: HEADACHE	Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 1173, 1985.
mouse	LD50	intramuscular	> 1gm/kg (1000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
mouse	LD50	intraperitoneal	> 2gm/kg (2000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
mouse	LD50	oral	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
rat	LD50	intramuscular	> 1gm/kg (1000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
rat	LD50	intraperitoneal	> 2gm/kg (2000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. -, Pg. 504, 1990.

5. Safety information of Cilostazol
Possible side effects of cilostazole use include headache (the most common), diarrhea, abnormal stools, increased heart rate, and palpitations. Although drugs similar to cilostazol have increased the risk of death in patients with congestive heart failure, studies of significant size have not addressed people without the disease.
Hazard Codes: Xi
WGK Germany: 2
RTECS: VC8277500

6. Production of Cilostazol
Cilostazole is manufactured by Otsuka Pharmaceutical Co. under the trade name Pletal. 5-chloro-N-cyclohexyl amyl amide of benzene solution can used to manufacture Cilostazole. But it will take place under the condition of Phosphorus pentachloride, benzene, ammonia and potassium hydroxide solution. All is showed as follows:



7. Uses of Cilostazol
Cilostazol (CAS NO.73963-72-1) is a medication used in the alleviation of the symptom of intermittent claudication in individuals with peripheral vascular disease. Cilostazol is a potent phosphodiesterase III A (PDE3A) inhibitor (IC50=0.2uM) and inhibitor of adenosine uptake. In addition, it has antimitogeni, antithrombotic, vasodilatory and cardiotonic properties in vivo. It can also affects lipid levels in vivo. Besides, it can also used in the clinical use. Cilostazol is a phosphodiesterase inhibitor with therapeutic focus on cAMP. It inhibits platelet aggregation and is a direct arterial vasodilator. Its main effects are dilation of the arteries supplying blood to the legs and decreasing platelet coagulation.