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Identification
NameMonobenzone
Accession NumberDB00600  (APRD01121)
Typesmall molecule
Groupsapproved
Description

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.

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
4-(Benzyloxy)phenolNot AvailableNot Available
Benzyl p-hydroxyphenyl etherNot AvailableNot Available
Hydrochinon monobenzyletherCzechNot Available
Hydroquinone benzyl etherNot AvailableNot Available
Hydroquinone monobenzyl etherNot AvailableNot Available
MonobenzonaSpanishINN
MonobenzoneFrenchINN
MonobenzonumLatinINN
Monobenzyl hydroquinoneNot AvailableNot Available
p-(Benzyloxy)phenolNot AvailableNot Available
p-Hydroxyphenyl benzyl etherNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
BenoquinNot Available
MonobenzoneVis
Brand mixturesNot Available
CategoriesNot Available
CAS number103-16-2
WeightAverage: 200.2332
Monoisotopic: 200.083729628
Chemical FormulaC13H12O2
InChI KeyInChIKey=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
Mass Specshow(7.31 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzylethers
Direct parentBenzylethers
Alternative parentsPhenol Ethers; Alkyl Aryl Ethers; Phenols and Derivatives; Enols; Polyamines
Substituentsphenol ether; phenol derivative; alkyl aryl ether; ether; enol; polyamine
Classification descriptionThis compound belongs to the benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Pharmacology
IndicationUsed topically to treat the loss of skin color (vitiligo).
PharmacodynamicsMonobenzone 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 actionMonobenzone is a depigmenting agent whose mechanism of action is not fully understood. 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9273
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
Packagers
Dosage forms
FormRouteStrength
CreamTopical
Prices
Unit descriptionCostUnit
Hydroquinone mono benzyl ether5.28USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point122 °CPhysProp
water solubility251 mg/LNot Available
logP3.2Not Available
Predicted Properties
PropertyValueSource
water solubility3.92e-02 g/lALOGPS
logP3.08ALOGPS
logP3.24ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)9.91ChemAxon
pKa (strongest basic)-4.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area29.46ChemAxon
rotatable bond count3ChemAxon
refractivity59.11ChemAxon
polarizability21.91ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05072
KEGG CompoundC14244
PubChem Compound7638
PubChem Substance46507466
ChemSpider7356
ChEBI34380
ChEMBLCHEMBL1388
Therapeutic Targets DatabaseDAP000830
PharmGKBPA164764582
Drug Product Database1966391
Drugs.comhttp://www.drugs.com/mtm/monobenzone-topical.html
WikipediaMonobenzone
ATC CodesD11AX13
AHFS Codes
  • 84:50.04
PDB EntriesNot Available
FDA labelshow(142 KB)
MSDSshow(36 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Tyrosinase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Tyrosinase P14679 Details

References:

  1. 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. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on January 20, 2014 22:07