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

General Information of Drug (ID: DR3329)
Drug Name
Ibrolipim
Synonyms Ibrolipim < Prop INN; NO-1886; OPF-009; 4-[N-(4-Bromo-2-cyanophenyl)carbamoyl]benzylphosphonic acid diethyl ester
Indication Hypertriglyceridaemia [ICD11: 5C80] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 451.2 Topological Polar Surface Area 88.4
Heavy Atom Count 27 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
131601
CAS Number
133208-93-2
TTD Drug ID
D0SA3J
Formula
C19H20BrN2O4P
Canonical SMILES
CCOP(=O)(CC1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)Br)C#N)OCC
InChI
InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
InChIKey
KPRTURMJVWXURQ-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
Ibrolipim metabolite M-1 DM015280
429740
Unclear - Unclear 1 [3]
Ibrolipim metabolite M-2 DM015169
131601
Unclear - Unclear 1 [3] , [2]
Ibrolipim metabolite M-3 DM015847
13745801
Unclear - Unclear 1 [3]
Ibrolipim metabolite M-4 DM015698
10512749
Oxidation - Hydroxylation 2 [3]
Ibrolipim metabolite M-5 DM015707
10685091
Conjugation - Sulfation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008497 Ibrolipim Ibrolipim metabolite M-1 Unclear - Unclear Unclear [3]
MR008500 Ibrolipim Ibrolipim metabolite M-3 Unclear - Unclear Unclear [3]
MR008501 Ibrolipim Ibrolipim metabolite M-2 Unclear - Unclear CYP3A4 ... [3], [2]
MR008498 Ibrolipim metabolite M-1 Ibrolipim metabolite M-4 Oxidation - Hydroxylation Unclear [3]
MR008499 Ibrolipim metabolite M-4 Ibrolipim metabolite M-5 Conjugation - Sulfation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 NO-1886 (ibrolipim), a lipoprotein lipase activator, increases the expression of uncoupling protein 3 in skeletal muscle and suppresses fat accumulation in high-fat diet-induced obesity in rats. Metabolism. 2005 Dec;54(12):1587-92.
2 Phosphonate O-deethylation of [4-(4-bromo-2-cyano-phenylcarbamoyl) benzyl]-phosphonic acid diethyl ester, a lipoprotein lipase-promoting agent, catalyzed by cytochrome P450 2C8 and 3A4 in human liver microsomes
3 Pharmacokinetics and metabolism of NO-1886, a lipoprotein lipase-promoting agent, in cynomolgus monkey

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