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 |
|---|---|---|---|
Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19610592 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
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| Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012-11-19 |
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| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
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| Metagenomic analysis of the turkey gut RNA virus community. | 2010-11-12 |
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| Effective melanoma immunotherapy in mice by the skin-depigmenting agent monobenzone and the adjuvants imiquimod and CpG. | 2010-05-13 |
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| Monobenzyl ether of hydroquinone and 4-tertiary butyl phenol activate markedly different physiological responses in melanocytes: relevance to skin depigmentation. | 2010-01 |
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| 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. | 2009-08 |
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| Guideline for the diagnosis and management of vitiligo. | 2008-11 |
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| New and experimental treatments of vitiligo and other hypomelanoses. | 2007-07 |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
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| Retinoic acid synergistically enhances the melanocytotoxic and depigmenting effects of monobenzylether of hydroquinone in black guinea pig skin. | 2006-07 |
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| [Studies on constituents from the fermentation of Alternalia sp]. | 2005-03 |
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| A novel site-directed affinity reagent for cross-linking human hemoglobin: bis[2-(4-phosphonooxyphenoxy)carbonylethyl]phosphinic acid. | 2004-11-18 |
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| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003-10 |
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| Superlite Plasma Collection System. | 2003-02 |
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| Vitiligo: a manifestation of apoptosis? | 2002 |
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| Influence of depigmenting chemical agents on hair and skin color in yellow (pheomelanic) and black (eumelanic) mice. | 1990-03-01 |
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
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C552
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CHEMBL1388
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