U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H8O2
Molecular Weight 124.1375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEQUINOL

SMILES

COc1ccc(cc1)O

InChI

InChIKey=NWVVVBRKAWDGAB-UHFFFAOYSA-N
InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

HIDE SMILES / InChI
Mequinol (mequinol is 4-hydroxyanisole) is an active ingredient in topical drugs used for skin depigmentation. The mechanism of action of mequinol is unknown. Although mequinol is a substrate for the enzyme tyrosinase and acts as a competitive inhibitor of the formation of melanin precursors, the clinical significance of these findings is unknown.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOLAGE

Approved Use

Mequinol is a depigmenting agent. The mechanism of depigmenting effects of mequinol remain unclear; speculations include oxidation by tyrosinase to cytotoxic products in melanocytes, a direct/selective toxic effect on melanocytes, or inhibition of melanin formation

Launch Date

9.4478402E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.92 ng/mL
16 μL 1 times / day steady-state, topical
dose: 16 μL
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
MEQUINOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
33.43 ng × h/mL
16 μL 1 times / day steady-state, topical
dose: 16 μL
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
MEQUINOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5 h
16 μL 1 times / day steady-state, topical
dose: 16 μL
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
MEQUINOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 % 1 times / day steady, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: steady
Dose: 2 %, 1 times / day
Co-administed with::
tretinoin(0.0001)
Sources:
healthy, 55.8 years
n = 159
Health Status: healthy
Condition: solar lentigines
Age Group: 55.8 years
Sex: M+F
Population Size: 159
Sources:
Disc. AE: Dermal and epidermal conditions NEC, Skin and subcutaneous tissue disorders...
Other AEs: Hematuria...
AEs leading to
discontinuation/dose reduction:
Dermal and epidermal conditions NEC (3.5%)
Skin and subcutaneous tissue disorders (5.8%)
Other AEs:
Hematuria (3.5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hematuria 3.5%
2 % 1 times / day steady, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: steady
Dose: 2 %, 1 times / day
Co-administed with::
tretinoin(0.0001)
Sources:
healthy, 55.8 years
n = 159
Health Status: healthy
Condition: solar lentigines
Age Group: 55.8 years
Sex: M+F
Population Size: 159
Sources:
Dermal and epidermal conditions NEC 3.5%
Disc. AE
2 % 1 times / day steady, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: steady
Dose: 2 %, 1 times / day
Co-administed with::
tretinoin(0.0001)
Sources:
healthy, 55.8 years
n = 159
Health Status: healthy
Condition: solar lentigines
Age Group: 55.8 years
Sex: M+F
Population Size: 159
Sources:
Skin and subcutaneous tissue disorders 5.8%
Disc. AE
2 % 1 times / day steady, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: steady
Dose: 2 %, 1 times / day
Co-administed with::
tretinoin(0.0001)
Sources:
healthy, 55.8 years
n = 159
Health Status: healthy
Condition: solar lentigines
Age Group: 55.8 years
Sex: M+F
Population Size: 159
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole.
2002 Dec
Metabolic activation of 4-hydroxyanisole by isolated rat hepatocytes.
2002 Oct
Enhancement of the depigmenting effect of hydroquinone and 4-hydroxyanisole by all-trans-retinoic acid (tretinoin): the impairment of glutathione-dependent cytoprotection?
2003
Anise oil as para-methoxyamphetamine (PMA) precursor.
2003 Apr 23
Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).
2003 Jan 1
Metabolic activation of 3-hydroxyanisole by isolated rat hepatocytes.
2003 Jan 6
A combination of ultrasound and oxidative enzyme: sono-biodegradation of substituted phenols.
2003 Jul
Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study.
2003 Jul 9
Fate of isoxaben in a containerized plant rhizosphere system.
2003 Mar
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].
2004
New drugs 04, part 1.
2004 Feb
Effect of phenolic mediators and humic acid on cyprodinil transformation in presence of birnessite.
2004 Jun
Safety and efficacy of combined use of 4-hydroxyanisole (mequinol) 2%/tretinoin 0.01% solution and sunscreen in solar lentigines.
2004 Oct
Structural close-related aromatic compounds have different effects on laccase activity and on lcc gene expression in the ligninolytic fungus Trametes sp. I-62.
2004 Oct
Sorption-desorption of alachlor and linuron in a semiarid soil as influenced by organic matter properties after 16 years of periodic inputs.
2005 Jun 29
Evaluation of urinary methoxyphenols as biomarkers of woodsmoke exposure.
2006 Apr 1
Inhibition of MMP-2 secretion from brain tumor cells suggests chemopreventive properties of a furanocoumarin glycoside and of chalcones isolated from the twigs of Dorstenia turbinata.
2006 Dec
Infrared spectroscopic characteristics of octa-substituted bis(phthalocyaninato) rare earth complexes peripherally substituted with (4-methoxy)phenoxy derivatives.
2006 Mar 1
Peroxidase-mediated removal of a polychlorinated biphenyl using natural organic matter as the sole cosubstrate.
2007 Feb 1
An investigation of the reduction in aqueous acetonitrile of 4-methoxybenzenediazonium ion by the tetrakis(acetonitrile)Cu(I) cation catalysed by hydrogenphosphate dianion.
2007 Feb 21
Subcellular localization and cytoplasmic complex status of endogenous Keap1.
2007 Oct
Electrochemical oxidation characteristics of p-substituted phenols using a boron-doped diamond electrode.
2007 Sep 15
A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid.
2008 Jun 5
Metabolic bioactivation and toxicity of ethyl 4-hydroxybenzoate in human SK-MEL-28 melanoma cells.
2008 May
Topical treatment of melasma.
2009
The hunt for natural skin whitening agents.
2009 Dec 10
Production of o-diphenols by immobilized mushroom tyrosinase.
2009 Jan 15
Current and emerging therapy for the management of vitiligo.
2009 Mar 12
Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO,O'}tris-(thio-cyanato-κN)europium(III).
2009 Nov 21
(E)-2-[(4-Ethoxy-phen-yl)imino-meth-yl]-4-methoxy-phenol.
2009 Oct 10
Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration.
2009 Sep 15
6,6'-Dimeth-oxy-2,2'-[(E,E')-(4-chloro-m-phenyl-ene)bis-(nitrilo-methyl-idyne)]diphenol.
2009 Sep 30
Antioxidant activity of colored rice bran obtained at different milling yields.
2010
In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury.
2010 Apr
Pi-selective stationary phases: (II) Adsorption behaviour of substituted aromatic compounds on n-alkyl-phenyl stationary phases.
2010 Aug 13
Molecular characteristics of Kraft-AQ pulping lignin fractionated by sequential organic solvent extraction.
2010 Aug 16
Synthesis and characterization of amine bridged bis(phenolate) lanthanide aryloxides and their application in the polymerization of lactide.
2010 Aug 7
Pairwise substitution effects, inter- and intramolecular hydrogen bonds in methoxyphenols and dimethoxybenzenes. Thermochemistry, calorimetry, and first-principles calculations.
2010 Dec 16
The influence of fibrous elastomer structure and porosity on matrix organization.
2010 Dec 22
Measurement of phenols dearomatization via electrolysis: the UV-Vis solid phase extraction method.
2010 Feb
Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach.
2010 Feb 12
Marine natural meroterpenes: synthesis and antiproliferative activity.
2010 Feb 23
Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers.
2010 Feb 26
Surface photochemistry of pesticides containing 4-chlorophenoxyl chromophore.
2010 Jul 15
Hydrogen hyperfine splitting constants for phenoxyl radicals by DFT methods: regression analysis unravels hydrogen bonding effects.
2010 Jul 21
Application of ex situ dynamic nuclear polarization in studying small molecules.
2010 Jun 14
Depigmentation therapy in vitiligo universalis with cryotherapy and 4-hydroxyanisole.
2010 Mar
Strategic distribution of protective proteins within bran layers of wheat protects the nutrient-rich endosperm.
2010 Mar
Heterogeneous reaction of gaseous ozone with aqueous iodide in the presence of aqueous organic species.
2010 May 20
Structure and vibrational frequencies of 6,7-dimethoxy-1,4-dihydro-1,3-quinoxalinedione based on density functional theory calculations: The role of pi-electron conjugation and back-donation.
2010 Sep 15
Patents

Sample Use Guides

Apply Solagé to the solar lentigines using the applicator tip while avoiding application to the surrounding skin. Use twice daily, morning and evening at least 8 hours apart, or as directed by a physician. Patients should not shower or bathe the treatment areas for at least 6 hours after application of Solagé. Special caution should be taken when applying Solagé to avoid the eyes, mouth, paranasal creases, and mucous membranes.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Name Type Language
MEQUINOL
HSDB   INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
SOLAGE COMPONENT MEQUINOL
Common Name English
4-METHOXYPHENOL
Systematic Name English
MEQUINOL [ORANGE BOOK]
Common Name English
MEQUINOL COMPONENT OF SOLAGE
Common Name English
MEQUINOL [MART.]
Common Name English
P-HYDROXYANISOLE
INCI  
INCI  
Official Name English
NSC-4960
Code English
MEQUINOL [USAN]
Common Name English
MEQUINOL [WHO-DD]
Common Name English
PHENOL, 4-METHOXY-
Systematic Name English
BMS-181158
Code English
P-HYDROXYANISOLE [INCI]
Common Name English
MEQUINOL [HSDB]
Common Name English
MEQUINOL [INN]
Common Name English
MEQUINOL [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78284
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
NDF-RT N0000175851
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
WHO-ATC D11AX06
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
NDF-RT N0000175855
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
NDF-RT N0000175850
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
CFR 21 CFR 176.170
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
WHO-VATC QD11AX06
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
Code System Code Type Description
DRUG BANK
DB09516
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
CAS
150-76-5
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL544
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
HSDB
4258
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
RXCUI
15080
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY RxNorm
FDA UNII
6HT8U7K3AM
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
INN
1542
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
IUPHAR
6827
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-769-8
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
EVMPD
SUB08764MIG
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
EPA CompTox
150-76-5
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
NCI_THESAURUS
C47604
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
DRUG CENTRAL
4221
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
MESH
C009760
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
PUBCHEM
9015
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY
WIKIPEDIA
MEQUINOL
Created by admin on Sat Jun 26 07:02:00 UTC 2021 , Edited by admin on Sat Jun 26 07:02:00 UTC 2021
PRIMARY