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
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
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 |
DescriptionSources: https://www.drugs.com/pro/benoquin.htmlCurator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19610592 |
Sources: https://www.drugs.com/pro/benoquin.html
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19610592 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BENOQUIN Approved UseThe 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 Date1952 |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Influence of depigmenting chemical agents on hair and skin color in yellow (pheomelanic) and black (eumelanic) mice. | 1990 Mar-Apr |
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Vitiligo: a manifestation of apoptosis? | 2002 |
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Superlite Plasma Collection System. | 2003 Feb |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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A novel site-directed affinity reagent for cross-linking human hemoglobin: bis[2-(4-phosphonooxyphenoxy)carbonylethyl]phosphinic acid. | 2004 Nov 18 |
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[Studies on constituents from the fermentation of Alternalia sp]. | 2005 Mar |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Guideline for the diagnosis and management of vitiligo. | 2008 Nov |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/benoquin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19657355
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
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Record UNII |
9L2KA76MG5
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Validated (UNII)
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FDA ORPHAN DRUG |
707519
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WHO-ATC |
D11AX13
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N0000175853
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NCI_THESAURUS |
C552
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NDF-RT |
N0000175851
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N0000175850
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QD11AX13
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CHEMBL1388
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588
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DB00600
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1445506
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C006429
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2132
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9L2KA76MG5
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SUB09049MIG
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7638
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m7604
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4019
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100000080360
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34380
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Monobenzone
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C992
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103-16-2
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17145
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203-083-3
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Related Record | Type | Details | ||
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