Compound: Cilomilast
SMILES: O=C(O)C1CCC(C#N)(c2cc(OC3CCCC3)c(OC)cc2)CC1
InChIKey: CFBUZOUXXHZCFB-UHFFFAOYSA-N
Synonyms: Cilomilast, 153259-65-5, Ariflo, SB-207499, 153259-69-9, trans-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid, SB207499, SB 207499, CIS-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANECARBOXYLIC ACID, Cilomilast-d9, 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid, 164414-71-5, 8ATB1C1R6X, CHEMBL27220, cis-4-Cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexanecarboxylic acid, CHEMBL511115, DTXSID6046686, NCGC00167520-01, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid, (1s,4s)-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid, Cilomilast [USAN:INN], CIO, 1794779-92-2, 4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexane-1-carboxylic acid, Ariflo (TN), UNII-8ATB1C1R6X, Cilomilast (JAN/USAN/INN), 1xlx, 1xom, cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid, cis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid, CILOMILAST [MI], CILOMILAST [INN], CILOMILAST [JAN], CILOMILAST [USAN], CILOMILAST [VANDF], CILOMILAST [MART.], CILOMILAST [WHO-DD], SCHEMBL26372, SCHEMBL27515, SCHEMBL27516, CHEMBL32854, Cilomilast (SB-207499), GTPL7407, orb1300763, DTXCID4026686, SCHEMBL13777301, BDBM14773, CHEBI:94683, DTXSID40861410, GLXC-06848, GLXC-25763, HMS3654F10, HMS3884K17, Cilomilast, SB 207499, Ariflo, CS-B1491, EX-A1554, UWC77992, Tox21_112517, BDBM50346088, BDBM50407414, MFCD28044030, PDSP1_001287, PDSP2_001271, s1455, 4-cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)cyclohexane-1-carboxylic acid, AKOS015967197, AKOS030526103, AKOS040759016, AT10133, CCG-267954, CS-0470, DB03849, SB19573, Cyclohexanecarboxylic acid, 4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-, cis-, NCGC00167520-03, NCGC00167520-06, NCGC00390705-01, NCGC00485415-01, CS-15164, DA-51903, HY-10790, MS-25260, CAS-153259-65-5, NS00073272, SW219280-1, C13118, D01704, SBI-0654063.0001, F788153, Q5120034, BRD-K38473998-001-02-0, BRD-K62982419-001-01-2, 6-(3,4-Dimethoxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one, 4-Cyano-3-cyclopentyloxy-4-(4-methoxy-phenyl)-cyclohexanecarboxylic acid, 4-Cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexanecarboxylic acid, 4-Cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)-cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentoxy)-4-methoxy-phenyl]cyclohexanecarboxylic acid, (1r,4r)-4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexane-1-carboxylic acid, (1r,4r)-4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexanecarboxylic acid, 4-Cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)-cyclohexanecarboxylic acid (Ariflo), 4-Cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)-cyclohexanecarboxylic acid methyl ester, 4-Cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)-cyclohexanecarboxylic acid(Ariflo), rel-(1s,4s)-4-Cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexane-1-carboxylic acid, rel-cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid, trans-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylicacid
Theoretical properties:
molecular_formula: C20H25NO4
molecular_weight: 343.4 g/mol
exact_mass: 343.17835828 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 5
heavy_atom_count: 25
topological_polar_surface_area: 79.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid is a member of methoxybenzenes.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Cilomilast (INN, development code SB-207,499, proposed trade name Ariflo) is a drug which was developed for the treatment of respiratory disorders such as asthma and chronic obstructive pulmonary disease (COPD). It is orally active and acts as a selective phosphodiesterase-4 inhibitor.
Phosphodiesterase (PDE) inhibitors, such as theophylline, have been used to treat COPD for centuries; however, the clinical benefits of these agents have never been shown to outweigh the risks of their numerous adverse effects. Four clinical trials were identified evaluating the efficacy of cilomilast, the usual randomized, double-blind, and placebo-controlled protocols were used. It showed reasonable efficacy for treating COPD, but side effects were problematic and it is unclear whether cilomilast will be marketed, or merely used in the development of newer drugs.
Cilomilast is a second-generation PDE4 inhibitor with anti-inflammatory effects that target bronchoconstriction, mucus hypersecretion, and airway remodeling associated with COPD.