(1s,4s)-4-cyano-4-{3-[(2H9)cyclopentyloxy]-4-methoxyphenyl}cyclohexane-1-carboxylic acid

• ChemBase ID: 164760
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: c1(ccc(cc1OC1CCCC1)[C@]1(CC[C@@H](CC1)C(=O)O)C#N)OC
• Canonical SMILES: N#C[C@@]1(CC[C@@H](CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
• InChI: InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)/t14-,20-
• InChIKey: CFBUZOUXXHZCFB-OYOVHJISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,4s)-4-cyano-4-{3-[(^2H₉)cyclopentyloxy]-4-methoxyphenyl}cyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1s,4s)-4-cyano-4-{3-[(^2H₉)cyclopentyloxy]-4-methoxyphenyl}cyclohexane-1-carboxylic acid
• Synonyms: cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic Acid; cis-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-4-cyanocyclohexane-1-carboxylic Acid; Ariflo; SB 207499; Cilomilast-d9

Database IDs

• PubChem SID: 162258895
• PubChem CID: 71314867

CALCULATED PROPERTIES

• Acid pKa: 2.327759
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.8856495
• LogD (pH = 7.4): 0.3828267
• Log P: 3.9000275
• Molar Refractivity: 93.0007 cm^3
• Polarizability: 36.371185 Å^3
• Polar Surface Area: 79.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C441432

Labelled Cilomilast. Selective phosphodiesterase 4 (PDE4) inhibitor. Antiasthmatic; used in treatment of chronic obstructive pulmonary disease.

REFERENCES

• Barnette, M.S., et al.: J. Pharmacol. Exp. Ther., 284, 420 (1998)
• Torphy, TJ., et al.: Pulm. Pharmacol. Ther., 12, 131 (1998)
• Zussman, B.D., et al.: Pharmacotherapy, 21, 653 (1998)
• Compton, C.H., et al.: Lancet, 358, 265 (1998)