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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
4-(Benzyloxyl)phenolNot AvailableNot Available
4-(Phenylmethoxy)phenolNot AvailableNot Available
4-Benzyloxy-phenolNot AvailableNot Available
4-BenzyloxyphenolNot 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 ether OF hydroquinoneNot AvailableNot Available
Monobenzyl hydroquinoneNot AvailableNot Available
p-(Benzyloxy)phenolNot AvailableNot Available
p-Hydroxyphenyl benzyl etherNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BenoquinNot Available
MonobenzoneVis
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number103-16-2
WeightAverage: 200.2332
Monoisotopic: 200.083729628
Chemical FormulaC13H12O2
InChI KeyVYQNWZOUAUKGHI-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Phenol
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9919
Blood Brain Barrier+0.9299
Caco-2 permeable+0.8883
P-glycoprotein substrateNon-substrate0.75
P-glycoprotein inhibitor INon-inhibitor0.8003
P-glycoprotein inhibitor IINon-inhibitor0.6474
Renal organic cation transporterNon-inhibitor0.7007
CYP450 2C9 substrateNon-substrate0.7753
CYP450 2D6 substrateNon-substrate0.8892
CYP450 3A4 substrateNon-substrate0.6895
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9273
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateNon-inhibitor0.9368
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6568
Ames testNon AMES toxic0.8925
CarcinogenicityNon-carcinogens0.7536
BiodegradationReady biodegradable0.528
Rat acute toxicity1.9160 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.828
hERG inhibition (predictor II)Non-inhibitor0.8828
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Hydroquinone mono benzyl ether5.28USD g
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 Solubility0.0392 mg/mLALOGPS
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 Area29.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.11 m3·mol-1ChemAxon
Polarizability21.91 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.31 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesD11AX13
AHFS Codes
  • 84:50.04
PDB EntriesNot Available
FDA labelDownload (142 KB)
MSDSDownload (36 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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