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
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 ether OF hydroquinone
  • Monobenzyl hydroquinone
  • p-(Benzyloxy)phenol
  • p-Hydroxyphenyl benzyl ether
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BenoquinCream200 mg/1gTopicalValeant Pharmaceuticals North America2017-12-102017-12-11Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benoquin Crm 20%Cream20 %TopicalValeant Canada Lp Valeant Canada S.E.C.1993-12-312014-07-30Canada
International/Other Brands
Benoquin / Monobenzone (Vis)
Categories
UNII
9L2KA76MG5
CAS number
103-16-2
Weight
Average: 200.2332
Monoisotopic: 200.083729628
Chemical Formula
C13H12O2
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

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.

TargetActionsOrganism
UTyrosinase
inhibitor
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014738
KEGG Drug
D05072
KEGG Compound
C14244
PubChem Compound
7638
PubChem Substance
46507466
ChemSpider
7356
BindingDB
50410520
ChEBI
34380
ChEMBL
CHEMBL1388
Therapeutic Targets Database
DAP000830
PharmGKB
PA164764582
Drugs.com
Drugs.com Drug Page
Wikipedia
Monobenzone
ATC Codes
D11AX13 — Monobenzone
FDA label
Download (142 KB)
MSDS
Download (36 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Valeant pharmaceuticals international
Packagers
  • Legacy Pharmaceuticals Packaging LLC
  • Professional Co.
  • Valeant Ltd.
Dosage forms
FormRouteStrength
CreamTopical200 mg/1g
CreamTopical20 %
Prices
Unit descriptionCostUnit
Hydroquinone mono benzyl ether5.28USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9273
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.31 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
4-alkoxyphenol / Phenoxy compound / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Monocyclic benzene moiety / Ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzyl ether (CHEBI:34380)

Targets

Kind
Protein
Organism
Human
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
  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. doi: 10.1021/jf802617a. [PubMed:19159217]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:47