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Identification
Name Monobenzone
Accession Number DB00600 (APRD01121)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Benzoquin
Benzyl hydroquinone
Benzyl p-hydroxyphenyl ether
Hydrochinon monobenzylether [Czech]
Hydroquinone benzyl ether
Hydroquinone monobenzyl ether
Monobenzona [INN-Spanish]
Monobenzone [INN]
Monobenzonum [INN-Latin]
Monobenzyl ether hydroquinone
Monobenzyl Ether of Hydroquinone
Monobenzyl hydroquinone
p-Hydroxyphenyl benzyl ether
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Salts Not Available
Brand names
Name Company
Agerite
AgeRite Alba
Alba
Alba-Dome
Benoquin
Carmifal
Depigman
Dermochinona
Leucodinine
Monobenzon
Pigmex
Superlite
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Brand mixtures Not Available
Categories
  • Dermatologicals
CAS number 103-16-2
Weight Average: 200.2332
Monoisotopic: 200.083729628
Chemical Formula C13H12O2
InChI Key InChIKey=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
Plain Text
IUPAC Name
4-(benzyloxy)phenol
SMILES
OC1=CC=C(OCC2=CC=CC=C2)C=C1
Plain Text
Mass Spec show (7.31 KB)
Taxonomy
Kingdom Organic
Classes
  • Methoxyphenols
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Hydroquinones
  • Methoxyphenols
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
Pharmacology
Indication Used topically to treat the loss of skin color (vitiligo).
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. 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.
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
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
Packagers
Dosage forms
Form Route Strength
Cream Topical
Prices
Unit description Cost Unit
Hydroquinone mono benzyl ether 5.28 USD 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 122 °C PhysProp
water solubility 251 mg/L Not Available
logP 3.2 Not Available
Predicted Properties
Property Value Source
water solubility 3.92e-02 g/l 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 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 59.11 ChemAxon
polarizability 21.91 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D05072 Link_out
KEGG Compound C14244 Link_out
PubChem Compound 7638 Link_out
PubChem Substance 46507466 Link_out
ChemSpider 7356 Link_out
ChEBI 34380 Link_out
ChEMBL 34380 Link_out
Therapeutic Targets Database DAP000830 Link_out
PharmGKB PA164764582 Link_out
Drug Product Database 1966391 Link_out
Drugs.com http://www.drugs.com/mtm/monobenzone-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Monobenzone Link_out
ATC Codes
  • D11AX13
AHFS Codes
  • 84:50.04
PDB Entries Not Available
FDA label show (142 KB)
MSDS show (36 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Tyrosinase

Pharmacological action: unknown
Actions: inhibitor

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 to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone

Organism class: human
UniProt ID: P14679 Link_out
Gene: TYR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19