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]
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) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
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
DrugBank ID
DB03849
TTD ID
D02EMR
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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.