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

General Information of Drug (ID: DR1893)
Drug Name
LAU-7b
Synonyms
FENRETINIDE; Fenretinida; Fenretinida [Spanish]; Fenretinide [USAN:INN]; Fenretinidum; Fenretinidum [Latin]; McN-R-1967; N-(4-Hydroxyphenyl)retinamide; Retinamide, N-(4-hydroxyphenyl)-; Retinoic acid p-hydroxyanilide; all-trans-4'-Hydroxyretinanilide; 15-[(4-hydroxyphenyl)amino]retinal; 4-(hydroxyphenyl)retinamide; 4-HPR; 4-Hydroxyphenyl retinamide; 4-hydroxy(phenyl)retinamide; 4-hydroxyphenylretinamide; 4HPR; 65646-68-6; CCRIS 3260; N-(4-Hydroxyphenyl)all-Trans Retinamide; Retinoic acid p-hydroxyphenylamide; UNII-187EJ7QEXL
Indication Macular degeneration [ICD11: 9B78] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 391.5 Topological Polar Surface Area 49.3
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5288209
ChEBI ID
CHEBI:42588
CAS Number
65646-68-6
TTD Drug ID
D08JAC
Formula
C26H33NO2
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
InChI
1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
InChIKey
AKJHMTWEGVYYSE-FXILSDISSA-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
4'-hydroxy 4-HPR DM003273
5288209
Unclear 1 [2]
4'-oxo 4-HPR DM003269
11258242
Unclear 1 [2]
4-HPR glucuronide DM003274 N. A. Unclear 1 [2]
4-MPR DM003276
6439546
Unclear 1 [3]
Dehydrogenated 4-HPR DM003275 N. A. Unclear 1 [3]
LAU-7b Metabolite L1 DM003270 N. A. Unclear 2 [3]
Hydroxy-4-oxo-4-HPR-O-glucuronide DM003271 N. A. Unclear 3 [3]
Hydroxy-4-oxo-4-HPR-O-sulfate DM003272 N. A. Unclear 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003704 LAU-7b 4'-oxo 4-HPR Unclear CYP2C8 ... [2]
MR003708 LAU-7b 4'-hydroxy 4-HPR Unclear CYP2C8 ... [2]
MR003709 LAU-7b 4-HPR glucuronide Unclear UGT1A3 ... [2]
MR003710 LAU-7b Dehydrogenated 4-HPR Unclear CYP3A4 [3]
MR003711 LAU-7b 4-MPR Unclear Unclear [3]
MR003705 4'-oxo 4-HPR LAU-7b Metabolite L1 Unclear Unclear [3]
MR003706 LAU-7b Metabolite L1 Hydroxy-4-oxo-4-HPR-O-glucuronide Unclear Unclear [3]
MR003707 LAU-7b Metabolite L1 Hydroxy-4-oxo-4-HPR-O-sulfate Unclear Unclear [3]
⏷ Show the Full List of 8 MR(s)
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]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT00003075) Fenretinide in Treating Patients With Cervical Neoplasia.
2 Characterization of the metabolism of fenretinide by human liver microsomes, cytochrome P450 enzymes and UDP-glucuronosyltransferases. Br J Pharmacol. 2011 Feb;162(4):989-99.
3 Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure

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