Identification
- Summary
Monobenzone is a hydroquinone derivative used to treat vitiligo.
- Generic Name
- Monobenzone
- DrugBank Accession Number
- DB00600
- Background
Monobenzone is the monobenzyl ether of hydroquinone used medically for depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. It exerts a depigmenting effect on skin of mammals by increasing the excretion of melanin from the melanocytes. It may also cause destruction of melanocytes and permanent depigmentation.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Monobenzone (DB00600)
- Weight
- Average: 200.2332
Monoisotopic: 200.083729628 - Chemical Formula
- C13H12O2
- Synonyms
- 4-(Benzyloxy)phenol
- 4-(Benzyloxyl)phenol
- 4-(Phenylmethoxy)phenol
- 4-Benzyloxy-phenol
- 4-Benzyloxyphenol
- Benzyl p-hydroxyphenyl ether
- Hydrochinon monobenzylether
- Hydroquinone benzyl ether
- Hydroquinone monobenzyl ether
- Monobenzona
- Monobenzone
- Monobenzonum
- Monobenzyl hydroquinone
- p-(Benzyloxy)phenol
- p-Hydroxyphenyl benzyl ether
Pharmacology
- Indication
Used topically to treat the loss of skin color (vitiligo).
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Monobenzone is the monobenzyl ether of hydroquinone. Monobenzone, applied topically to the skin, is used as a depigmenting agent inhibitting melanin produced by polymerization of oxidation products of tyrosine and dihydroxyphenyl compounds. Monobenzone works by permanently removing color from normal skin located around skin with vitiligo.
- Mechanism of action
Monobenzone is a depigmenting agent whose mechanism of action is not fully understood. It is proposed that it increases the excretion of melanin from the melanocytes. 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. Following skin depigmentation after topical application of monobenzone, the histological studies indicate similar results as that seen in vitiligo, where the epidermis is intact but with the absence of identifiable melanocytes.
Target Actions Organism UTyrosinase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAgalsidase alfa The therapeutic efficacy of Agalsidase alfa can be decreased when used in combination with Monobenzone. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Monobenzone (Vis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Benoquin Cream 200 mg/1g Topical Valeant Pharmaceuticals North America 2017-12-10 2017-12-11 US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Benoquin Crm 20% Cream 20 % Topical Valeant Canada Lp Valeant Canada S.E.C. 1993-12-31 2014-07-30 Canada 
Categories
- ATC Codes
- D11AX13 — Monobenzone
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- 4-alkoxyphenols
- Direct Parent
- 4-alkoxyphenols
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 4-alkoxyphenol / Alkyl aryl ether / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Phenol ether
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzyl ether (CHEBI:34380)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9L2KA76MG5
- CAS number
- 103-16-2
- InChI Key
- VYQNWZOUAUKGHI-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
- IUPAC Name
- 4-(benzyloxy)phenol
- SMILES
- OC1=CC=C(OCC2=CC=CC=C2)C=C1
References
- General References
- FDA Approved Products: Benoquin (monobenzone) cream [Link]
- External Links
- Human Metabolome Database
- HMDB0014738
- KEGG Drug
- D05072
- KEGG Compound
- C14244
- PubChem Compound
- 7638
- PubChem Substance
- 46507466
- ChemSpider
- 7356
- BindingDB
- 50410520
- 17145
- ChEBI
- 34380
- ChEMBL
- CHEMBL1388
- ZINC
- ZINC000000001748
- Therapeutic Targets Database
- DAP000830
- PharmGKB
- PA164764582
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Monobenzone
- FDA label
- Download (142 KB)
- MSDS
- Download (36 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Valeant pharmaceuticals international
- Packagers
- Legacy Pharmaceuticals Packaging LLC
- Professional Co.
- Valeant Ltd.
- Dosage Forms
Form Route Strength Cream Topical 200 mg/1g Cream Topical 20 % Powder 1 g/1g - Prices
Unit description Cost Unit Hydroquinone mono benzyl ether 5.28USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 122 °C PhysProp water solubility 251 mg/L Not Available logP 3.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0392 mg/mL ALOGPS logP 3.08 ALOGPS logP 3.24 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 9.91 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.46 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 59.11 m3·mol-1 Chemaxon Polarizability 21.91 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9919 Blood Brain Barrier + 0.9299 Caco-2 permeable + 0.8883 P-glycoprotein substrate Non-substrate 0.75 P-glycoprotein inhibitor I Non-inhibitor 0.8003 P-glycoprotein inhibitor II Non-inhibitor 0.6474 Renal organic cation transporter Non-inhibitor 0.7007 CYP450 2C9 substrate Non-substrate 0.7753 CYP450 2D6 substrate Non-substrate 0.8892 CYP450 3A4 substrate Non-substrate 0.6895 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9273 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.9368 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6568 Ames test Non AMES toxic 0.8925 Carcinogenicity Non-carcinogens 0.7536 Biodegradation Ready biodegradable 0.528 Rat acute toxicity 1.9160 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.828 hERG inhibition (predictor II) Non-inhibitor 0.8828
Spectra
- Mass Spec (NIST)
- Download (7.31 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Protein homodimerization activity
- Specific Function
- This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA ...
- Gene Name
- TYR
- Uniprot ID
- P14679
- Uniprot Name
- Tyrosinase
- Molecular Weight
- 60392.69 Da
References
- Chen YR, Y-Y R, Lin TY, Huang CP, Tang WC, Chen ST, Lin SB: 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. doi: 10.1021/jf802617a. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 06, 2022 13:40