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73963-72-1

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Basic Information
CAS No.: 73963-72-1
Name: Cilostazol
Molecular Structure:
Molecular Structure of 73963-72-1 (Cilostazol)
Formula: C20H27N5O2
Molecular Weight: 369.467
Synonyms: 6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-3,4-dihydro-1H-quinolin-2-one;Pletal;OPC 13013;Cilostazol (JAN/USAN);2(1H)-Quinolinone,6-[4-(1-cyclohexyl-1Htetrazol- 5-yl)butoxy]-3,4-dihydro-;Pletal (TN);Cilostazole;Cilostal;
EINECS: 689-122-9
Density: 1.34 g/cm3
Melting Point: 159-160 °C
Boiling Point: 664.7 °C at 760 mmHg
Flash Point: 355.8 °C
Solubility: DMSO: 18 mg/mL, soluble
Appearance: off-white solid
Hazard Symbols: IrritantXi
PSA: 81.93000
LogP: 3.60270
Synthetic route
877303-65-6

cilostazol bisulfate

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water Product distribution / selectivity;98.7%
877303-63-4

cilostazol oxalate

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water Product distribution / selectivity;97.9%
877303-64-5

cilostazol malate

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water Product distribution / selectivity;97.8%

C20H26BrN5O2

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In acetonitrile for 10h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Reflux;96%
54197-66-9

3,4-dihydro-6-hydroxy-2(1H)-quinolinone

73963-42-5

1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With potassium carbonate; sodium hydroxide; sodium sulfite In ethanol for 8h; Reflux;92.5%
With potassium carbonate; sodium hydroxide; sodium sulfite In water at 92℃; for 6h; Solvent; Reagent/catalyst; Temperature;91.5%
With potassium hydroxide In ethanol at 80℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;90%
54197-66-9

3,4-dihydro-6-hydroxy-2(1H)-quinolinone

73963-42-5

1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole

A

865792-18-3

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)-butoxy]-1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)-butyl]-3,4-dihydro-1H-quinolin-2-one

B

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

C

73963-62-9

OPC 13015

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 75 - 80℃;A n/a
B 89%
C n/a

C20H26ClN5O2

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 25℃; for 8h; Inert atmosphere;88%

C20H26IN5O2

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 25℃; for 8h; Inert atmosphere;85%
73963-42-5

1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
Stage #1: 3,4-dihydro-6-hydroxy-2(1H)-quinolinone With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 6.5h; Heating / reflux; Molecular sieve;
Stage #2: 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole In ethanol for 6.5h; Product distribution / selectivity; Heating / reflux;
40.2%
Multi-step reaction with 4 steps
1: sodium hydroxide / butan-1-ol / 8 h / Reflux
2: iron; ammonium chloride; acetic acid / methanol; water / 5 h / 45 °C / Reflux
3: triethylamine / dichloromethane / 3 h / 0 °C
4: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 10 h / Inert atmosphere; Reflux
View Scheme
104-94-9

4-methoxy-aniline

73963-72-1

6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 0.5 h
2: aluminum (III) chloride / N,N-dimethyl acetamide / 2 h / 150 °C
3: potassium hydroxide / ethanol / 12 h / 80 °C / Inert atmosphere; Sealed tube
View Scheme
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  • Casno:

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Specification

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: IrritantXi
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:

Production of Cilostazol

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.