68550-75-4

Usage

Uses

Used in Pharmaceutical Industry:
Cilostamide is used as a serotonin receptor ligand for its potential role in modulating serotonin signaling pathways, which can have implications in the treatment of various neurological and psychiatric disorders.
Used in Research and Development:
Cilostamide is used as a specific phosphodiesterase 3 (PDE3) inhibitor in research and development for studying the role of PDE3 in various physiological processes and its potential therapeutic applications.
Used in Obesity and Metabolic Research:
Cilostamide is used in obesity and metabolic research for its ability to reverse the effect of leptin on food intake and body weight, providing insights into the development of potential treatments for obesity and related metabolic disorders.

Biological Activity

Selective inhibitor of type III phosphodiesterase (PDE3). Displays moderate selectivity for PDE3A isozyme vs. PDE3B (IC 50 values are 0.027 and 0.050 μ M for PDE3A and PDE3B respectively). Inhibits ADP-induced platelet aggregation (IC 50 = 16.8 μ M); anti-thrombotic. Also available as part of the Phosphodiesterase Inhibitor Tocriset? .

Biochem/physiol Actions

Selective inhibitor of PDE3 (cGMP-inhibited phosphodiesterase); IC50 = 70 ± 9 nM. This inhibitory effect increases intracellular cAMP and inhibits platelet aggregation.

References

1) Hidaka et al. (1979), Selective inhibitor of platelet cyclic adenosine monophosphate phosphodiesterase, cilostamide, inhibits platelet aggregation; J. Pharmacol. Exp. Ther., 211 26 2) Christensen and Torphy et al. (1994), Isozyme-Selective Phosphodiesterase Inhibitors as Antiasthmatic Agents; Annu. Rep. Med. Chem., 29 185 3) Ahmad et al. (2000), Cyclic nucleotide phosphodiesterase 3B is a downstream target of protein kinase B and may be involved in regulation of effects of protein kinase B on thymidine incorporation in FDCP2 cells; J. Immunol., 164 4678 4) Zhao et al. (2002), A phosphatidylinositol 3-kinase phosphodiesterase 3B-cyclic AMP pathway in hypothalamic action of leptin on feeding; Nat. Neuroscience, 5 727

InChI:InChI=1/C20H26N2O3/c1-22(16-6-3-2-4-7-16)20(24)8-5-13-25-17-10-11-18-15(14-17)9-12-19(23)21-18/h9-12,14,16H,2-8,13H2,1H3,(H,21,23)

Upstream product

• 42454-06-8 2-nitro-5-hydroxybenzaldehyde 
• 19315-93-6 6-hydroxy-1H-quinolin-2-one 
• 58900-36-0 ethyl 4-(1,2-dihydro-2-oxoquinolin-6-yloxy)butanoate 
• 104-94-9 4-methoxy-aniline 
• 100-60-7 N-methylcyclohexylamine 
• 58899-33-5 4-(2-oxo-1,2-dihydro-quinolin-6-yloxy)-butyric acid 
• 87364-41-8 methyl 4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyrate 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 94193-38-1 N-Cyclohexyl-N-methyl-4-(3-formyl-4-nitrophenyl)-oxybutyramide 
• 94193-37-0 4-(3-Formyl-4-nitro-phenoxy)-butyryl chloride 
• 94193-36-9 4-(3-formyl-4-nitrophenyl)oxybutanoic acid 
• 105763-50-6 N-cyclohexyl-N-methyl-4-<3-(2-carboxyvinyl)-4-nitrophenoxy>butyramide 
• 94193-35-8 ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate 
• 105763-72-2 (E)-3-{2-Amino-5-[3-(cyclohexyl-methyl-carbamoyl)-propoxy]-phenyl}-acrylic acid 

Downstream Products

• 69601-00-9 N-cyclohexyl-N-methyl-4-(1,2-dihydro-1-methyl-2-oxo-6-quinolyloxy)butyramide 
• 69600-96-0 4-(1-Benzyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-N-cyclohexyl-N-methyl-butyramide 
• 151640-63-0 6-[3-(N-cyclohexyl-N-methylaminothiocarbonyl)propoxy]carbostyril 

Relevant academic research and scientific papers

New procedure for the total synthesis of cilostamide

An efficient route to synthesise a wide range of N,N-R,R-4-(2-oxo-1,2- dihydroquinolin-6-yloxy)butanamide, specially Cilostamide (R = methyl and R = cyclohexyl), one of the most selective inhibitors of phosphodiesterase3 (PDE3) enzyme, from 5-methoxy-2-ni

Inhibitors of cyclic AMP phosphodiesterase. 1. Analogues of cilostamide and anagrelide

Evaluation of a series of lactam heterocyclic analogues of cilostamide as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide afforded the hybrid structure RS-82856, shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.

Substituted carbostyrils as inhibitors of cyclic AMP phosphodiesterase

A series of 6-substituted carbostyrils has been synthesized and tested as inhibitors of two vascular smooth muscle phosphodiesterases, one of them selective for cyclic AMP and the other calmodulin dependent and selective for cyclic GMP. The inhibitory act

Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. III. N-cyclohexyl-N-(2-hydroxyethyl)-4-(1,2-dihydro-2-oxo-6-quinolyloxy) butyramide and related compounds

A series of N,N-disubstituted-ω-(1,2-dihydro-2-oxoquinolyloxy)alkanecarboxamides was synthesized and tested for inhibitory activity towards collagen- and ADP-induced aggregation of rabbit blood platelet in vitro. These compounds were prepared by the react

NOVEL CARBOSTYRIL DERIVATIVES

Novel carbostyril derivatives having platelet aggregation inhibitory action, antiinflamatory action, antiulcer action, vasodilatory action and phosphodiesterase inhibitory action and are useful for preventing or curing thrombus, arteriosclerosis, hypertension, asthma and other like diseases, and also useful as an antiinflamatory or anti-ulcer agent, represented by the formula wherein R1 is hydrogen, C1-4 alkyl, C2-4 alkenyl, phenyl-C1-4 alkyl-; R2 is hydrogen, a halogen atom, hydroxy, phenyl-C1-4 alkoxy; R3 is hydrogen, hydroxy, C1-4 alkyl; R4 is C3-8 cycloalkyl, substituted or unsubstituted phenyl, C3-8 cycloalkyl-C1-4 alkyl, 2-(3,4-dimethoxyphenyl)-ethyl, R5 is hydrogen, C1-8 alkyl, C2-4 alkenyl, phenyl, C3-8 cycloalkyl, phenyl-C1-4 alkyl, C3-8 cycloalkyl-C1-4 alkyl, m is an integer of 1 - 3, l and n which may be same or different, and are respectively 0 or an integer of 1 - 7 and the sum of l and n is not exceeding 7, the carbon-carbon bond at 3- and 4-positions in the carbostyril skelton is either single or double bond