Details of the Drug

General Information of Drug (ID: DMHSM7I)

Drug Name

Cilomilast

Synonyms

Ariflo; CIO; SB 207499; SB207499; Ariflo (TN); Cilomilast [USAN:INN]; SB-207499; Ariflo, SB-207499,Cilomilast; Cilomilast (JAN/USAN/INN); CIS-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANECARBOXYLIC ACID; Cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid; Cis-4-Cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclohexanecarboxylic acid; Cis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid; 4-cyano-4-(3-cyclopentoxy-4-methoxy-phenyl)-cyclohexane-1-carboxylic acid; 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Bronchitis	CA20	Discontinued in Phase 3	[1]
Chronic obstructive pulmonary disease	CA22	Discontinued in Phase 3	[1]
Emphysema	CA21	Discontinued in Phase 3	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

343.4

Logarithm of the Partition Coefficient (xlogp)

3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H25NO4
IUPAC Name: 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid
Canonical SMILES: COC1=C(C=C(C=C1)C2(CCC(CC2)C(=O)O)C#N)OC3CCCC3
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)
InChIKey: CFBUZOUXXHZCFB-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 151170
ChEBI ID: CHEBI:94683
CAS Number: 153259-65-5
UNII: 8ATB1C1R6X
DrugBank ID: DB03849
TTD ID: D02EMR

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Phosphodiesterase 4 (PDE4)	TTV5CGO	NOUNIPROTAC	Inhibitor	[2]
Phosphodiesterase 4A (PDE4A)	TTZ97H5	PDE4A_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B)	OTOA8WU2	PDE4B_HUMAN	Gene/Protein Processing	[4]
3',5'-cyclic-AMP phosphodiesterase 4C (PDE4C)	OTI8VMHZ	PDE4C_HUMAN	Gene/Protein Processing	[4]
3',5'-cyclic-AMP phosphodiesterase 4D (PDE4D)	OT1RWFV0	PDE4D_HUMAN	Gene/Protein Processing	[4]
Interferon gamma (IFNG)	OTXG9JM7	IFNG_HUMAN	Protein Interaction/Cellular Processes	[4]
Interleukin-4 (IL4)	OTOXBWAU	IL4_HUMAN	Protein Interaction/Cellular Processes	[4]
Interleukin-5 (IL5)	OTAFPSCO	IL5_HUMAN	Protein Interaction/Cellular Processes	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7407).
2	Emerging drugs for the treatment of chronic obstructive pulmonary disease. Expert Opin Emerg Drugs. 2006 May;11(2):275-91.
3	Emerging drugs for asthma. Expert Opin Emerg Drugs. 2008 Dec;13(4):643-53.
4	Pharmacological profile of a novel phosphodiesterase 4 inhibitor, 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridin-6-yl)-benzoic acid (NVP-ABE171), a 1,7-naphthyridine derivative, with anti-inflammatory activities. J Pharmacol Exp Ther. 2002 Apr;301(1):241-8. doi: 10.1124/jpet.301.1.241.