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

General Information of Drug (ID: DR0208)
Drug Name
Bexarotene
Synonyms
Bexaroten; Bexarotene; LG 100069; LG 1069; LG-100069; LG100069; LGD 1069; LGD-1069; LGD1069; Targret; Targretin; Targretyn; Targrexin; bexarotenum; 153559-49-0; 166175-31-1; 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid; 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid; A61RXM4375; CHEBI:50859; CHEMBL1023; HSDB 7453; MFCD00932428; UNII-A61RXM4375; p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
Indication Anaplastic large cell lymphoma [ICD11: 2A90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 348.5 Topological Polar Surface Area 37.3
Heavy Atom Count 26 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
82146
PubChem SID
7978490 ; 10219206 ; 11528625 ; 14876119 ; 17397261 ; 43137306 ; 46509119 ; 50125754 ; 50156197 ; 53790324 ; 56310969 ; 56313259 ; 56313930 ; 56352964 ; 57288573 ; 57333349 ; 74382986 ; 85246146 ; 87550948 ; 92308910 ; 93167039 ; 103274364 ; 103941130 ; 104379861 ; 118314715 ; 124893632 ; 124893633 ; 125341807 ; 126591248 ; 126646347 ; 126667092 ; 127324027 ; 127324028 ; 127324029 ; 127324030 ; 127324031 ; 127324032 ; 127324033 ; 128675752 ; 131300153 ; 131407703 ; 134220606 ; 134337590 ; 135037531 ; 135650520 ; 135692419 ; 136340346 ; 136946490 ; 137002663 ; 142405765
ChEBI ID
ChEBI:50859
CAS Number
153559-49-0
TTD Drug ID
D0N0RU
Formula
C24H28O2
Canonical SMILES
CC1=CC2=C(C=C1C(=C)C3=CC=C(C=C3)C(=O)O)C(CCC2(C)C)(C)C
InChI
1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
InChIKey
NAVMQTYZDKMPEU-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
7-hydroxy-bexarotene DM001414
71748830
Unclear 1 [3]
6-hydroxy-bexarotene DM001415
10067357
Unclear 2 [3]
7-oxo-bexarotene. DM001416
101142043
Unclear 3 [3]
6-oxo-bexarotene. DM001417
101142042
Unclear 4 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003189 Bexarotene 7-hydroxy-bexarotene Unclear Unclear [3]
MR003186 7-hydroxy-bexarotene 6-hydroxy-bexarotene Unclear Unclear [3]
MR003187 6-hydroxy-bexarotene 7-oxo-bexarotene. Unclear Unclear [3]
MR003188 7-oxo-bexarotene. 6-oxo-bexarotene. Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Bexarotene was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Bexarotene metabolism in rat, dog, and human, synthesis of oxidative metabolites, and in vitro activity at retinoid receptors Drug Metab Dispos. 2001 Jul;29(7):990-8.

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