N-cyclohexyl-N-methyl-4-[(2-oxo-1,2-dihydroquinolin-6-yl)oxy]butanamide

• ChemBase ID: 105642
• Molecular Formular: C20H26N2O3
• Molecular Mass: 342.43204
• Monoisotopic Mass: 342.1943427
• SMILES: CN(C1CCCCC1)C(=O)CCCOc1cc2c([nH]c(=O)cc2)cc1
• Canonical SMILES: O=C(N(C1CCCCC1)C)CCCOc1ccc2c(c1)ccc(=O)[nH]2
• InChI: InChI=1S/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)
• InChIKey: UIAYVIIHMORPSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-cyclohexyl-N-methyl-4-[(2-oxo-1,2-dihydroquinolin-6-yl)oxy]butanamide
• IUPAC Traditional name: N-cyclohexyl-N-methyl-4-[(2-oxo-1H-quinolin-6-yl)oxy]butanamide
• Synonyms: 6-[3-(N-Cyclohexyl-N-methylcarbamoyl)propoxy]quinolin-2[1H]-one; OPC 3689; Cilostamide; N-Cyclohexyl-N-methyl-4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyramide; CILOSTAMIDE

Database IDs

• CAS Number: 68550-75-4
• MDL Number: MFCD00673958
• PubChem SID: 24278337; 162093847
• PubChem CID: 2753

CALCULATED PROPERTIES

• Acid pKa: 14.516282
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8828053
• LogD (pH = 7.4): 2.8828082
• Log P: 2.8828084
• Molar Refractivity: 99.9112 cm^3
• Polarizability: 37.563183 Å^3
• Polar Surface Area: 58.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... PDE3A(5139), PDE3B(5140), PDE5A(8654), PDE7A(5150)rat ... Pde2a(81743), Pde4a(25638)

DETAILS

MP Biomedicals - 02193635

Inhibitor of cGMP-inhibited phosphodiesterase.

Sigma Aldrich - C7971

Biochem/physiol Actions
Selective inhibitor of PDE3 (cGMP-inhibited phosphodiesterase); IC50 = 70 ± 9 nM. This inhibitory effect increases intracellular cAMP and inhibits platelet aggregation.1