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

General Information of Drug (ID: DR0835)
Drug Name
Hydroquinone
Synonyms
Hidroquinone; Hydrochinon; Hydrochinone; Hydroquinole; Idrochinone; Phiaquin; Quinol; Solaquin forte; Tecquinol; Tenox HQ; Tequinol; Usaf ek-356; hydroquinol; hydroquinone; p-Benzenediol; p-Dihydroxybenzene; p-Dioxybenzene; Arctuvin; Benzene, p-dihydroxy-; Benzene-1,4-diol; Benzohydroquinone; Benzoquinol; Derma-Blanch; Diak 5; Dihydroquinone; Dihydroxybenzene; Eldopaque; Eldopaque Forte; Eldoquin; Eldoquin Forte; p-Hydroquinone; p-Hydroxyphenol; 1,4-Dihydroxy-benzol; 1,4-Dihydroxybenzene; 1,4-benzenediol; 123-31-9; 4-Hydroxyphenol; Artra
Indication Melasma [ICD11: ED60] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 110.11 Topological Polar Surface Area 40.5
Heavy Atom Count 8 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
785
PubChem SID
2806 ; 3812 ; 74764 ; 588856 ; 596756 ; 3133423 ; 3727025 ; 5137602 ; 7847141 ; 8139895 ; 8144595 ; 8150790 ; 10505937 ; 11111286 ; 11342040 ; 11362223 ; 11364651 ; 11367213 ; 11369775 ; 11371611 ; 11374385 ; 11377937 ; 11485619 ; 11487625 ; 11489488 ; 11490472 ; 11492448 ; 11495571 ; 14709376 ; 14842848 ; 17389853 ; 17405139 ; 24278475 ; 24439146 ; 24895484 ; 24895587 ; 24895884 ; 26612686 ; 26679214 ; 26747267 ; 26747268 ; 36588004 ; 41135091 ; 46484887 ; 46500618 ; 47885526 ; 48110568 ; 48259371 ; 48413875 ; 48417398
ChEBI ID
ChEBI:17594
CAS Number
123-31-9
TTD Drug ID
D03UOT
Formula
C6H6O2
Canonical SMILES
C1=CC(=CC=C1O)O
InChI
1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
InChIKey
QIGBRXMKCJKVMJ-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
2,3,5-tris(glutathion-S-yl)Hydroquinone DM002549
101644674
Unclear 1 [4]
p-Benzoquinone DM002548
4650
Oxidation - Oxidation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001157 Hydroquinone p-Benzoquinone Oxidation - Oxidation Mpo [5]
MR001158 Hydroquinone 2,3,5-tris(glutathion-S-yl)Hydroquinone Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Fumarate reductase flavoprotein (frdA) DME1059 Wolinella succinogenes
FRDA_WOLSU
1.3.5.4
[3]
References
1 ClinicalTrials.gov (NCT01661556) Clinical Trial of Hydroquinone Versus Miconazol in Melasma.
2 Metabolism of (S)-5,6-difluoro-4-cyclopropylethynyl-4-trifluoromethyl-3, 4-dihydro-2(1H)-quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics. Drug Metab Dispos. 2003 Jan;31(1):122-32.
3 Wolinella succinogenes quinol:fumarate reductase and its comparison to E. coli succinate:quinone reductase. FEBS Lett. 2003 Nov 27;555(1):21-8.
4 Carcinogenicity of a nephrotoxic metabolite of the "nongenotoxic" carcinogen hydroquinone Chem Res Toxicol. 2001 Jan;14(1):25-33. doi: 10.1021/tx000161g.
5 Hydroquinone, a bioreactive metabolite of benzene, inhibits apoptosis in myeloblasts Stem Cells. 1996 Nov;14(6):730-42. doi: 10.1002/stem.140730.

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