Identification

Name
Hydroquinone
Accession Number
DB09526
Type
Small Molecule
Groups
Approved, Investigational
Description

Hydroquinone is a topical lightening product found in OTC products, and is used to correct skin discoloration associated with disorders of hyperpigmentation including melasma, post-inflammatory hyperpigmention, sunspots, and freckles. It can be used alone, but is more frequently found in combination with other agents such as alpha-hydroxy acids, corticosteroids, retinoids, or sunscreen.

Hydroquinone has come under scrutiny due to several complications associated with its use, including dermal irritation, exogenous onchronosis, and carginogenicity. As a result of these concerns, hydroquinone has been banned in the EU and UK.

Structure
Thumb
Synonyms
  • 1,4-benzenediol
  • 1,4-dihydroxybenzene
  • 4-Hydroxyphenol
  • benzene-1,4-diol
  • p-Benzenediol
  • p-Hydroquinone
  • p-hydroxyphenol
  • quinol
External IDs
CHEBI:17594 / CHEMBL537 / NCI-C55834 / NSC-9247
Active Moieties
NameKindUNIICASInChI Key
Phenolunknown339NCG44TV108-95-2ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Active 4Cream4 %TopicalVivier Canada Incorporated2005-09-06Not applicableCanada
Clear Essence Advance Complex Fade GelGel2 %TopicalBluefield Associates, Inc.Not applicableNot applicableCanada
Clear Essence Skin Lightening GelGel2 %TopicalBluefield Associates, Inc.Not applicableNot applicableCanada
Clear Essence Skin Lightening MilkLotion2 %TopicalBluefield Associates, Inc.Not applicableNot applicableCanada
Clear-N-SmoothCream2 %TopicalHawknad Manufacturing Industries, Inc.Not applicableNot applicableCanada
Corrector 4Cream4 %TopicalVivier Canada Incorporated2005-09-06Not applicableCanada
Eldopaque Forte Crm 4%Cream4 %TopicalValeant Canada Lp Valeant Canada S.E.C.1993-12-31Not applicableCanada
Eldoquin ForteCream4 %TopicalValeant Canada Lp Valeant Canada S.E.C.1992-12-31Not applicableCanada
LustraCream4 %TopicalTaropharma, A Division Of Taro Pharmaceuticals Inc.2001-04-09Not applicableCanada
Seequin 4 IdsGel4 %TopicalVivier Canada Incorporated2003-01-13Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accelerated Dark Spot CorrectorCream2 g/100mLTopicalCosmetic Enterprises2017-06-12Not applicableUs
Activator LightLotion2 g/100mLTopicalVivier Pharma2013-09-01Not applicableUs
Active 4Cream4 g/100mLTopicalVivier Pharma2014-05-30Not applicableUs
Advanced Dual Complex Fade Maximum Strength PlusGel2 g/100gTopicalBiocosmetics Research Labs2009-02-25Not applicableUs
Advanced Skin Lightening CreamLotion2 g/100mLTopicalVivier Pharma2016-06-01Not applicableUs
Advanced Skin Lightening SerumGel2 %TopicalVivier Canada Incorporated2003-01-29Not applicableCanada
Advanced Skin Lightening SerumGel20 mg/1mLTopicalVivier Pharma2017-11-06Not applicableUs
Advanced Skin Lightening SerumLiquid2 g/100mLTopicalVivier Pharma2016-09-302018-12-01Us
African Formula BlackCream1 g/50gTopicalInternational Beauty Exchange2011-01-01Not applicableUs
African Formula CarrotCream1 g/50gTopicalInternational Beauty Exchange2011-03-11Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Advanced LightningHydroquinone (0.02 g/1g) + Octinoxate (0.02 g/1g)CreamTopicalCBI Laboratories, Inc2005-07-01Not applicableUs
African Formula Skin LighteningHydroquinone (5 mL/250mL) + Octinoxate (1.25 mL/250mL)LotionTopicalInternational Beauty Exchange2012-01-01Not applicableUs
African Formula Skin LighteningHydroquinone (1 g/50g) + Octinoxate (.25 g/50g)CreamTopicalInternational Beauty Exchange2011-01-01Not applicableUs
Ambi Fade Normal SkinHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalJohnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc.2012-05-302013-07-01Us
AMBI Fade Normal SkinHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalValeant Pharmaceuticals North America2014-02-04Not applicableUs
AMBI Fade Oily SkinHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalValeant Pharmaceuticals North America2013-11-01Not applicableUs
Ambi Fade Oily SkinHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalJohnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc.2012-04-112013-07-01Us
Ambi Skincare Normal Skin FadeHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalL'oreal2017-08-24Not applicableUs
AMBI Skincare Oily Skin FadeHydroquinone (20 mg/1g) + Octinoxate (20 mg/1g)CreamTopicalL'oreal2017-10-02Not applicableUs
Artra Skin Tone for Dry SkinHydroquinone (20 mg/1g) + Homosalate (75 mg/1g) + Oxybenzone (25 mg/1g)CreamTopicalJ. Strickland & Co.1990-12-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Aclaro HydroquinoneHydroquinone (40 mg/1g)EmulsionTopicalInnocutis2004-06-012016-05-23Us
Aclaro PD HydroquinoneHydroquinone (40 mg/1g)EmulsionTopicalInnocutis Holdings, LLC2011-04-012014-04-30Us
Alphaquin HPHydroquinone (40 mg/1g) + Octinoxate (75 mg/1g) + Oxybenzone (50 mg/1g)CreamTopicalStratus Pharmaceuticals1993-01-012017-02-01Us
BalancerHydroquinone (40 mg/1g)CreamTopicalAxia Medical Solutions, Llc1990-12-01Not applicableUs
CenoviaHydroquinone (2 g/2g) + Fluticasone propionate (0.025 g/0.025g) + Tretinoin (0.025 g/0.025g)KitAccumix Pharmaceuticals2014-12-152015-07-17Us
CONDITION AND ENHANCE BLENDER Skin Lightener and BlendingHydroquinone (40 mg/1g)CreamTopicalOMP, INC.1988-01-01Not applicableUs
CONDITION AND ENHANCE CLEAR Skin Bleaching and CorrectorHydroquinone (40 mg/1g)CreamTopicalOMP, INC.1988-01-01Not applicableUs
Condition and Enhance System Full-size Non-surgicalHydroquinone (40 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (75 mg/1mL) + Zinc oxide (90 mg/1mL)KitOMP, INC.2007-08-20Not applicableUs
Condition and Enhance System Full-size Non-surgicalHydroquinone (40 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (75 mg/1mL) + Zinc oxide (90 mg/1mL)KitOMP, INC.2007-08-20Not applicableUs
Condition and Enhance System Travel-size Non-surgicalHydroquinone (40 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (75 mg/1mL) + Zinc oxide (90 mg/1mL)KitOMP, INC.2007-08-20Not applicableUs
International/Other Brands
Eldoquin
Categories
UNII
XV74C1N1AE
CAS number
123-31-9
Weight
Average: 110.1106
Monoisotopic: 110.036779436
Chemical Formula
C6H6O2
InChI Key
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
InChI
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
IUPAC Name
benzene-1,4-diol
SMILES
OC1=CC=C(O)C=C1

Pharmacology

Indication

Hydroquinone is used as an OTC topical lightening agent for disorders of hyperpigmentation including melasma, post-inflammatory hyperpigmention, sunspots and freckles.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

Hydroquinone reduces melanin pigment production through inhibition of the tyrosinase enzyme, which is involved in the initial step of the melanin pigment biosynthesis pathway. Hydroquinone takes several months to take effect.

TargetActionsOrganism
ATyrosinase
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Matsumoto M, Todo H, Akiyama T, Hirata-Koizumi M, Sugibayashi K, Ikarashi Y, Ono A, Hirose A, Yokoyama K: Risk assessment of skin lightening cosmetics containing hydroquinone. Regul Toxicol Pharmacol. 2016 Aug 10. pii: S0273-2300(16)30226-4. doi: 10.1016/j.yrtph.2016.08.005. [PubMed:27521610]
  2. Chen Y, Chen J, Yun L, Xu L, Liu J, Xu Y, Yang H, Liang H, Tang H: Hydroquinone-induced malignant transformation of TK6 cells by facilitating SIRT1-mediated p53 degradation and up-regulating KRAS. Toxicol Lett. 2016 Aug 8. pii: S0378-4274(16)33093-4. doi: 10.1016/j.toxlet.2016.08.006. [PubMed:27515134]
  3. Gbetoh MH, Amyot M: Mercury, hydroquinone and clobetasol propionate in skin lightening products in West Africa and Canada. Environ Res. 2016 Jul 1;150:403-410. doi: 10.1016/j.envres.2016.06.030. [PubMed:27372064]
  4. Findlay GH, Morrison JG, Simson IW: Exogenous ochronosis and pigmented colloid milium from hydroquinone bleaching creams. Br J Dermatol. 1975 Dec;93(6):613-22. [PubMed:1220808]
External Links
Human Metabolome Database
HMDB0002434
KEGG Drug
D00073
KEGG Compound
C00530
PubChem Compound
785
PubChem Substance
310265227
ChemSpider
764
BindingDB
26190
ChEBI
17594
ChEMBL
CHEMBL537
PharmGKB
PA449924
HET
HQE
Drugs.com
Drugs.com Drug Page
Wikipedia
Hydroquinone
ATC Codes
D11AX11 — Hydroquinone
AHFS Codes
  • 84:50.04 — Depigmenting Agents
PDB Entries
3zod / 3zof / 4e3h / 4qop / 5fse / 5i3a / 5i3b
FDA label
Download (1.15 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
2CompletedTreatmentMelasma / Picoseconds Laser1
2CompletedTreatmentBenign facial lentigines1
3CompletedTreatmentFacial Melasma1
3CompletedTreatmentMelasma1
3Not Yet RecruitingTreatmentChloasma / Melanosis / Melasma1
4CompletedTreatmentHyperpigmentation / Melasma1
4CompletedTreatmentMelasma1
4TerminatedTreatmentMelasma1
4Unknown StatusTreatmentMelanosis1
4Unknown StatusTreatmentMelasma1
Not AvailableCompletedPreventionSolar Lentigines1
Not AvailableCompletedTreatmentMelasma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical4 %
GelTopical2 g/100g
GelTopical2 %
GelTopical20 mg/1mL
LotionTopical20 mg/1mL
GelTopical2 g/100mL
LotionTopical2 g/14.25g
CreamTopical4 g/100mL
CreamCutaneous10 mL/500mL
LotionCutaneous10 mL/500mL
CreamTopical40 mg/1g
Kit
LotionTopical
CreamTopical2 g/100mL
LotionTopical.02 mg/1g
LotionTopical2.0 g/100mL
EmulsionTopical2.0 g/100mL
LotionTopical40 mg/1g
CreamTopical2 %
CreamTopical4 g/100g
CreamTopical4 mg/1g
CreamTopical20 mg/1g
CreamTopical1.5 %
CreamCutaneous4 mL/200mL
LotionCutaneous4 mL/200mL
LotionTopical2 %
GelTopical40 mg/1g
CreamTopical100 mg/5mg
CreamTopical5 mg/100mg
CreamTopical1 g/50mL
CreamTopical2 g/50mL
LotionTopical2 g/100mL
CreamTopical40 mg/1mL
CreamTopical1.9 g/100g
EmulsionTopical0.02 g/1g
EmulsionTopical0.04 g/1g
CreamTopical20 mg/1mL
CreamTopical2 g/100g
ClothTopical2 g/100mL
CreamTopical0.04 g/1g
LiquidTopical30 mg/1mL
GelTopical
CreamTopical1.695 g/113g
CreamTopical1 g/50g
GelTopical10 g/100mL
GelTopical0.02 g/1g
EmulsionTopical40 mg/1g
LiquidTopical40 mg/1mL
LiquidTopical40 mg/1g
SolutionTopical40 mg/1mL
LotionTopical0.05 mg/2.5mL
LotionTopical1.95 1/100mL
CreamTopical
GelTopical.6 g/30g
LotionTopical2 mg/100mL
LotionTopical0.015 g/1g
LotionTopical0.04 g/1g
LotionTopical1.2 mL/60mL
CreamTopical2.0 g/100mL
KitTopical
CreamTopical2 mL/100mL
LiquidTopical20 mg/1mL
LiquidTopical2 g/100mL
LiquidTopical4 g/100mL
GelTopical4 %
GelTopical1 g/50g
CreamTopical0.02 g/1g
CreamTopical2 mg/100mL
LiquidTopical2 mL/100mL
LiquidTopical8 g/100g
LiquidTopical0.02 g/1g
LiquidTopical0.08 g/1g
LotionTopical0.02 g/1g
CreamTopical4 mg/100mg
GelTopical20 mg/1g
CreamTopical19 mg/1g
CreamTopical1 g/51g
LiquidTopical2.0 g/100mL
LiquidTopical2.0 mL/100mL
LiquidTopical40 g/2mL
EmulsionTopical40 mg/1mL
EmulsionTopical0.04 g/1mL
EmulsionTopical0.04 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8247395No2012-08-212022-10-22Us
US8653053No2014-02-182022-10-25Us
US7939516No2011-05-102025-05-04Us
US7915243No2011-03-292026-03-22Us

Properties

State
Not Available
Experimental Properties
PropertyValueSource
melting point (°C)170-171O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 891
boiling point (°C)285-287O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 891
water solubility6.72g/L at 20 deg CYalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 254
logP0.59Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 20
Predicted Properties
PropertyValueSource
Water Solubility95.5 mg/mLALOGPS
logP0.71ALOGPS
logP1.37ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m3·mol-1ChemAxon
Polarizability10.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0f79-2490000000-6b4fec222a3499d93790
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9800000000-c90fd4986fea9691ecbf
GC-MS Spectrum - EI-BGC-MSsplash10-03e9-9300000000-f8b11742557329691e8a
GC-MS Spectrum - GC-MSGC-MSsplash10-0f79-2490000000-6b4fec222a3499d93790
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f79-2690000000-7306adcc7121a11d67cc
Mass Spectrum (Electron Ionization)MSsplash10-03di-9500000000-1fa8477944a662535e76
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-9600000000-e670ba090cb27367db12
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-01p6-9000000000-5fc32c7688c1612df1e7
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-c5853ce8ef225ea5c353
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-03di-9800000000-c90fd4986fea9691ecbf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-8d8328e4f7cd2ebaa27d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-9290fcb93f170fc3143f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01si-9200000000-9f707b9d0c4ad0b73b30
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-d3aae38632ac4c40fd4f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-74f15490ba4f49cf8c18
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9800000000-1cb01248e88fce387578
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0a4i-0900000000-5635f0157cd37deb1121
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2900000000-05be113033a709130eed
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroquinones. These are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Benzenediols
Direct Parent
Hydroquinones
Alternative Parents
1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Hydroquinone / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
hydroquinones, benzenediol (CHEBI:17594) / an electron-transfer-related quinol, a benzenediol (HYDROQUINONE)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Patil S, Sistla S, Jadhav J: Interaction of small molecules with human tyrosinase: A surface plasmon resonance and molecular docking study. Int J Biol Macromol. 2016 Aug 9;92:1123-1129. doi: 10.1016/j.ijbiomac.2016.07.043. [PubMed:27519292]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [PubMed:8831264]

Drug created on November 30, 2015 12:10 / Updated on December 10, 2018 13:39