Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3043)
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 Bronchitis [ICD11: CA20] Discontinued in Phase 3 [1]
Chronic obstructive pulmonary disease [ICD11: ICD11: CA22] Discontinued in Phase 3 [2]
Emphysema [ICD11: ICD11: CA21] Discontinued in Phase 3 [3]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 343.4 Topological Polar Surface Area 79.6
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
151170
ChEBI ID
CHEBI:94683
CAS Number
153259-65-5
TTD Drug ID
D02EMR
Formula
C20H25NO4
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Cilomilast Metabolite M32 DM017882 N. A. Unclear - Unclear 1 [5]
Cilomilast Metabolite M33 DM016211
59094642
Unclear - Unclear 1 [5]
Cilomilast Metabolite M34 DM017883 N. A. Unclear - Unclear 1 [5]
Cilomilast Metabolite M6 DM015951
17779515
Oxidation - Decyclopentylation 1 [5]
Cilomilast Metabolite M9 DM017876 N. A. Oxidation - 3-hydroxylation 1 [5] , [4]
Cilomilast Metabolite M1 DM017879 N. A. Unclear - Unclear 2 [5]
Cilomilast Metabolite M24 DM017880 N. A. Unclear - Unclear 2 [5]
Cilomilast Metabolite M35 DM017881 N. A. Unclear - Unclear 2 [5]
Cilomilast Metabolite M39 DM017878 N. A. Unclear - Unclear 2 [5]
Cilomilast Metabolite M5 DM017877 N. A. Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009433 Cilomilast Cilomilast Metabolite M9 Oxidation - 3-hydroxylation CYP2C8 [5], [4]
MR009435 Cilomilast Cilomilast Metabolite M6 Oxidation - Decyclopentylation Unclear [5]
MR009440 Cilomilast Cilomilast Metabolite M32 Unclear - Unclear Unclear [5]
MR009441 Cilomilast Cilomilast Metabolite M33 Unclear - Unclear Unclear [5]
MR009442 Cilomilast Cilomilast Metabolite M34 Unclear - Unclear Unclear [5]
MR009436 Cilomilast Metabolite M6 Cilomilast Metabolite M39 Unclear - Unclear Unclear [5]
MR009437 Cilomilast Metabolite M6 Cilomilast Metabolite M1 Unclear - Unclear Unclear [5]
MR009438 Cilomilast Metabolite M6 Cilomilast Metabolite M24 Unclear - Unclear Unclear [5]
MR009439 Cilomilast Metabolite M6 Cilomilast Metabolite M35 Unclear - Unclear Unclear [5]
MR009434 Cilomilast Metabolite M9 Cilomilast Metabolite M5 Unclear - Unclear Unclear [5]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
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 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).
3 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).
4 Cilomilast: a second generation phosphodiesterase 4 inhibitor for asthma and chronic obstructive pulmonary disease
5 Clinical pharmacology of Cilomilast

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.