Details of the Drug

General Information of Drug (ID: DM6AVR4)

Drug Name
Hydroquinone
Synonyms
hydroquinone; 1,4-benzenediol; Benzene-1,4-diol; 123-31-9; 1,4-Dihydroxybenzene; Quinol; p-Benzenediol; p-Hydroxyphenol; p-Hydroquinone; 4-Hydroxyphenol; Eldoquin; Benzoquinol; p-Dihydroxybenzene; hydroquinol; Eldopaque; Phiaquin; p-Dioxybenzene; Hydroquinole; Dihydroquinone; Tecquinol; Idrochinone; Benzohydroquinone; Tequinol; Hidroquinone; Arctuvin; Dihydroxybenzene; Solaquin forte; Derma-Blanch; Tenox HQ; Hydrochinone; Hydrochinon; Artra; Eldoquin Forte; Eldopaque Forte; Diak 5; Benzene, p-dihydroxy-; 1,4-Dihydroxy-benzol; Usaf ek-356; Accutin
Indication
Disease Entry ICD 11 Status REF
Melasma ED60.1 Approved [1]
ATC Code
D11AX11: Hydroquinone
D11AX: Other dermatologicals
D11A: OTHER DERMATOLOGICAL PREPARATIONS
D11: OTHER DERMATOLOGICAL PREPARATIONS
D: DERMATOLOGICALS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 110.11
Logarithm of the Partition Coefficient (xlogp) 0.6
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C6H6O2
IUPAC Name
benzene-1,4-diol
Canonical SMILES
C1=CC(=CC=C1O)O
InChI
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
InChIKey
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
785
ChEBI ID
CHEMBL537
CAS Number
123-31-9
UNII
XV74C1N1AE
DrugBank ID
DB09526
TTD ID
D03UOT
INTEDE ID
DR0835
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glycoprotein IIb/IIIa receptor (GPIIb/IIIa) TT38RM1 ITA2B_HUMAN ; ITB3_HUMAN Antagonist [2]
Tyrosinase (TYR) TTULVH8 TYRO_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Fumarate reductase flavoprotein (frdA) DEQUXZ5 FRDA_WOLSU Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein sigma (SFN) OTLJCZ1U 1433S_HUMAN Gene/Protein Processing [6]
17-beta-hydroxysteroid dehydrogenase type 2 (HSD17B2) OT3K7HY5 DHB2_HUMAN Gene/Protein Processing [7]
2'-5'-oligoadenylate synthase 1 (OAS1) OT8ZLOCY OAS1_HUMAN Gene/Protein Processing [7]
2'-5'-oligoadenylate synthase 2 (OAS2) OT64CCTM OAS2_HUMAN Gene/Protein Processing [7]
2'-5'-oligoadenylate synthase-like protein (OASL) OTZ05YRP OASL_HUMAN Gene/Protein Processing [8]
2-5A-dependent ribonuclease (RNASEL) OTP6UQUP RN5A_HUMAN Gene/Protein Processing [7]
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B) OTOA8WU2 PDE4B_HUMAN Gene/Protein Processing [7]
3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase FUT3 (FUT3) OTXQ6P8R FUT3_HUMAN Gene/Protein Processing [7]
6-phosphogluconolactonase (PGLS) OTO6C0IQ 6PGL_HUMAN Gene/Protein Processing [9]
Actin filament-associated protein 1 (AFAP1) OTR473H8 AFAP1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Melasma
ICD Disease Classification ED60.1
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Tyrosinase (TYR) DTT TYR 6.68E-04 2.54 1.15
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 2.19E-08 -5.72E-01 -1.61E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Accutin, a new disintegrin, inhibits angiogenesis in vitro and in vivo by acting as integrin alphavbeta3 antagonist and inducing apoptosis. Blood. 1998 Nov 1;92(9):3268-76.
3 Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis. J Agric Food Chem. 2009 Mar 25;57(6):2200-5.
4 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.
5 Wolinella succinogenes quinol:fumarate reductase and its comparison to E. coli succinate:quinone reductase. FEBS Lett. 2003 Nov 27;555(1):21-8.
6 Hydroquinone increases 5-hydroxymethylcytosine formation through ten eleven translocation 1 (TET1) 5-methylcytosine dioxygenase. J Biol Chem. 2013 Oct 4;288(40):28792-800. doi: 10.1074/jbc.M113.491365. Epub 2013 Aug 12.
7 Keratinocyte-derived IL-36gama plays a role in hydroquinone-induced chemical leukoderma through inhibition of melanogenesis in human epidermal melanocytes. Arch Toxicol. 2019 Aug;93(8):2307-2320.
8 Differently expressed long noncoding RNAs and mRNAs in TK6 cells exposed to low dose hydroquinone. Oncotarget. 2017 Oct 4;8(56):95554-95567. doi: 10.18632/oncotarget.21481. eCollection 2017 Nov 10.
9 [Differential proteomic expression in human liver cells stimulated by hydroquinone]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2006 Nov;24(11):658-61.