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Details

Stereochemistry ACHIRAL
Molecular Formula C13H12O2
Molecular Weight 200.2332
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOBENZONE

SMILES

OC1=CC=C(OCC2=CC=CC=C2)C=C1

InChI

InChIKey=VYQNWZOUAUKGHI-UHFFFAOYSA-N
InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2

HIDE SMILES / InChI

Description

Monobenzone is a topical drug used for medical depigmentation. The mechanism of action of monobenzone is not fully understood. Monobenzone is oxidized by tyrosinase from melanocytes to a toxic quinones which induce non-apoptotic melanocyte cell death.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BENOQUIN
Primary
PubMed

PubMed

TitleDatePubMed
Influence of depigmenting chemical agents on hair and skin color in yellow (pheomelanic) and black (eumelanic) mice.
1990 Mar-Apr
[Studies on constituents from the fermentation of Alternalia sp].
2005 Mar
Retinoic acid synergistically enhances the melanocytotoxic and depigmenting effects of monobenzylether of hydroquinone in black guinea pig skin.
2006 Jul
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
New and experimental treatments of vitiligo and other hypomelanoses.
2007 Jul
Guideline for the diagnosis and management of vitiligo.
2008 Nov
A reactive ortho-quinone generated by tyrosinase-catalyzed oxidation of the skin depigmenting agent monobenzone: self-coupling and thiol-conjugation reactions and possible implications for melanocyte toxicity.
2009 Aug
Monobenzyl ether of hydroquinone and 4-tertiary butyl phenol activate markedly different physiological responses in melanocytes: relevance to skin depigmentation.
2010 Jan
Effective melanoma immunotherapy in mice by the skin-depigmenting agent monobenzone and the adjuvants imiquimod and CpG.
2010 May 13
Metagenomic analysis of the turkey gut RNA virus community.
2010 Nov 12
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.
2012 Nov 19
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Sample Use Guides

In Vivo Use Guide
A thin layer of Benoquin Cream 20% should be applied and rubbed into the pigmented area two or three times daily, or as directed by physician. Prolonged exposure to sunlight should be avoided during treatment with Benoquin Cream 20%, or a sunscreen should be used.
Route of Administration: Topical
In Vitro Use Guide
Cell viability was measured by MTT assays according to manufacturer’s instructions. In brief, 20,000 cells per well were plated in triplicate wells of a 96-well plate to attach overnight. Cells were either treated with vehicle alone or with 250 or 500 mM of Monobenzone (MBEH) for 24 hours. MBEH (Sigma) was dissolved in 20% dimethyl sulfoxide and mixed with 70% ethanol for a stock concentration of 250mM. The use of a vehicle control refers to the use of 20% dimethyl sulfoxide in 70% ethanol. MTT reagent (tetrazole) was added to the cells and incubated in a 371C humidified chamber for 4 hours. Tetrazole is converted to formazan in the mitochondria of living cells. The formazan crystals formed were dissolved in solubilization buffer and the absorbance was read in a spectrophotometer at a wavelength of 562nm (BMG Labtech, Durham, NC). Cell viability was calculated as a percentage of absorbance of the samples relative to untreated control. Treatment with MBEH caused dose-dependend cell death.
Name Type Language
MONOBENZONE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
BENOQUIN
Brand Name English
MONOBENZONE [MART.]
Common Name English
MONOBENZONE [ORANGE BOOK]
Common Name English
P-(BENZYLOXY)PHENOL
Common Name English
MONOBENZONE [HSDB]
Common Name English
MONOBENZONE [INN]
Common Name English
MONOBENZONE [USP-RS]
Common Name English
MONOBENZONE [USP]
Common Name English
MONOBENZONE [WHO-DD]
Common Name English
MONOBENZONE [MI]
Common Name English
MONOBENZONE [VANDF]
Common Name English
PHENOL, 4-(PHENYLMETHOXY)-
Systematic Name English
HYDROQUINONE MONOBENZYL ETHER
Systematic Name English
NSC-2132
Code English
Classification Tree Code System Code
WHO-ATC D11AX13
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
NDF-RT N0000175853
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
NCI_THESAURUS C552
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
NDF-RT N0000175851
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
NDF-RT N0000175850
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
WHO-VATC QD11AX13
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1388
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
INN
588
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
DRUG BANK
DB00600
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
MESH
C006429
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
EVMPD
SUB09049MIG
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
PUBCHEM
7638
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
MERCK INDEX
M7604
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY Merck Index
HSDB
103-16-2
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
WIKIPEDIA
Monobenzone
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
NCI_THESAURUS
C992
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
CAS
103-16-2
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
IUPHAR
6830
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
EPA CompTox
103-16-2
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY
RXCUI
17145
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
203-083-3
Created by admin on Tue Oct 22 05:23:51 UTC 2019 , Edited by admin on Tue Oct 22 05:23:51 UTC 2019
PRIMARY