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Details

Stereochemistry ACHIRAL
Molecular Formula C13H12O2
Molecular Weight 200.2332
Optical Activity NONE
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

Molecular Formula C13H12O2
Molecular Weight 200.2332
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19610592 |

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

Approved Use

The topical application of monobenzone in animals, increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans. Monobenzone may cause destruction of melanocytes and permanent depigmentation. This effect is erratic and may take one to four months to occur while existing melanin is lost with normal sloughing of the stratum corneum. Hyperpigmented skin appears to fade more rapidly than does normal skin, and exposure to sunlight reduces the depigmenting effect of the drug. The histology of the skin after depigmentation with topical monobenzone is the same as that seen in vitiligo; the epidermis is normal except for the absence of identifiable melanocytes.

Launch Date

-5.40950397E11
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Vitiligo: a manifestation of apoptosis?
2002
[Studies on constituents from the fermentation of Alternalia sp].
2005 Mar
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
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:04:46 UTC 2023
Edited
by admin
on Sat Dec 16 16:04:46 UTC 2023
Record UNII
9L2KA76MG5
Record Status Validated (UNII)
Record Version
  • Download
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 [MI]
Common Name English
Monobenzone [WHO-DD]
Common Name English
MONOBENZONE [VANDF]
Common Name English
PHENOL, 4-(PHENYLMETHOXY)-
Systematic Name English
HYDROQUINONE MONOBENZYL ETHER
Systematic Name English
NSC-2132
Code English
MONOBENZONE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 707519
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
WHO-ATC D11AX13
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
NDF-RT N0000175853
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
NCI_THESAURUS C552
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
NDF-RT N0000175851
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
NDF-RT N0000175850
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
WHO-VATC QD11AX13
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1388
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
INN
588
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PRIMARY
DRUG BANK
DB00600
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PRIMARY
RS_ITEM_NUM
1445506
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PRIMARY
MESH
C006429
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
NSC
2132
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
FDA UNII
9L2KA76MG5
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
EVMPD
SUB09049MIG
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PRIMARY
PUBCHEM
7638
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PRIMARY
MERCK INDEX
m7604
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PRIMARY Merck Index
HSDB
4019
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PRIMARY
SMS_ID
100000080360
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PRIMARY
CHEBI
34380
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
WIKIPEDIA
Monobenzone
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
NCI_THESAURUS
C992
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
CAS
103-16-2
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
IUPHAR
6830
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
DRUG CENTRAL
1834
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID2020717
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
RXCUI
17145
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
203-083-3
Created by admin on Sat Dec 16 16:04:46 UTC 2023 , Edited by admin on Sat Dec 16 16:04:46 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY