CIO

CILOMILAST

Created:	2004-10-18
Last modified:	2021-03-01

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2 entries where CIO is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	0
Bond Count	52
Aromatic Bond Count	6

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Chemical Component Summary
Name	CILOMILAST
Synonyms	CIS-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANECARBOXYLIC ACID
Systematic Name (OpenEye OEToolkits)	4-cyano-4-(3-cyclopentyloxy-4-methoxy-phenyl)cyclohexane-1-carboxylic acid
Formula	C₂₀ H₂₅ N O₄
Molecular Weight	343.417
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C3CCC(C#N)(c2cc(OC1CCCC1)c(OC)cc2)CC3
SMILES	CACTVS	3.341	COc1ccc(cc1OC2CCCC2)[C]3(CC[CH](CC3)C(O)=O)C#N
SMILES	OpenEye OEToolkits	1.5.0	COc1ccc(cc1OC2CCCC2)C3(CCC(CC3)C(=O)O)C#N
Canonical SMILES	CACTVS	3.341	COc1ccc(cc1OC2CCCC2)[C@]3(CC[C@@H](CC3)C(O)=O)C#N
Canonical SMILES	OpenEye OEToolkits	1.5.0	COc1ccc(cc1OC2CCCC2)C3(CCC(CC3)C(=O)O)C#N
InChI	InChI	1.03	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	InChI	1.03	CFBUZOUXXHZCFB-OYOVHJISSA-N

Drug Info: DrugBank

DrugBank ID	DB03849
Name	Cilomilast
Groups	investigational
Description	Cilomilast (Ariflo, SB-207,499) 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. Following four clinical trials, the drug proved to be effective in treating COPD, however it has never been marketed due to a poor side effect profile.
Synonyms	Ariflo Cilomilast cis-4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexanecarboxylic acid
Indication	Investigated for use/treatment in chronic obstructive pulmonary disease (COPD).
Categories	Acids, Carbocyclic Cyclohexanes Cycloparaffins Enzyme Inhibitors Phosphodiesterase 4 Inhibitors Phosphodiesterase Inhibitors
CAS number	153259-65-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
cAMP-specific 3',5'-cyclic phosphodiesterase 4D	MEAEGSSAPARAGSGEGSDSAGGATLKAPKHLWRHEQHHQYPLRQPQFRL...	unknown	inhibitor
cAMP-specific 3',5'-cyclic phosphodiesterase 4B	MKKSRSVMTVMADDNVKDYFECSLSKSYSSSSNTLGIDLWRGRRCCSGNL...	unknown	inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682