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{{Chembox new
{{DrugProjectFormSinglePage
|authorTag={{KS}}
|genericName=hydroquinone
|aOrAn=a
|drugClass=dermatological agent
|indicationType=treatment
|indication=discoloration of skin, [[hyperpigmentation]] of skin
|adverseReactions=burning sensation, [[contact dermatitis]], [[erythema|localized erythema]]
|blackBoxWarningTitle=Warning Title
|blackBoxWarningBody=<i><span style="color:#FF0000;">Condition Name:</span></i> (Content)
|fdaLIADAdult===Indications==
* Skin Lightening
* To gradually lighten [[hyperpigmentation]] of the skin such as age spots, [[liver spots]], [[freckles]] or [[hyperpigmentation]] that can occur as a result of pregnancy or the use of oral contraceptives.
 
==Dosing==
* Use fingertips to apply a thin layer to affected areas. Use both morning and night or as directed by a physician. Gradual lightening of the discolored area can be expected in most cases.
|offLabelAdultGuideSupport===Indications and Dosage==
* Discoloration of skin: emulsion, apply topically twice daily to affected area(s) or as directed by physician for no longer than 2 months.
 
* Hyperpigmentation of skin: cream and gel, with or without sunscreens, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; rub in well.
 
* Hyperpigmentation of skin: cream with sunblock, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; do not rub in.
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of Hydroquinone in adult patients.
|offLabelPedGuideSupport===Indications and Dosage==
* Safety and efficacy not established in children less than 12 years of age; not recommended for use except under physician supervision.
 
* Discoloration of skin: 12 years and older; emulsion, apply topically twice daily to affected area(s) or as directed by physician for no longer than 2 months.
 
* Hyperpigmentation of skin: 12 years and older; cream and gel, with or without sunscreens, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; rub in well.
 
* Hyperpigmentation of skin: 12 years and older; cream with sunblock, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; do not rub in.
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of Hydroquinone in pediatric patients.
|contraindications=* Hypersensitivity to hydroquinone or any component of hydroquinone products.
* Pregnancy, safety not established.
* Children 12 years of age and under; safety not established.
|warnings=There is limited information regarding <i>Warnings</i> of Hydroquinone in  patients.
|postmarketing=Dermatologic: Burning sensation, [[contact dermatitis]], localized [[erythema]]
|drugInteractions=There is limited information regarding <i>Drug Interactions</i> of Hydroquinone in  patients.
|othersTitle=Others
|administration='''Topical'''
* Avoid exposure of treated areas to sunlight.
* Avoid contact with eyes.
|monitoring=* Repigmentation
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of Hydroquinone in  patients.
|overdose=There is limited information regarding <i>Overdose</i> of Hydroquinone in  patients.
|drugBox={{chembox2
| Watchedfields = changed
| verifiedrevid = 443862076
|  Name = Hydroquinone
|  ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Hydrochinon2.png
|  ImageSize =
|  ImageName = Hydroquinone
|  ImageName = Hydroquinone
|  ImageFile1 = Hydroquinone-3d.png
|  ImageFile1 = Trans-hydroquinone-from-xtal-3D-balls.png
<!-- | ImageSize1 = 150px  -->
|   ImageSize1 =
|  IUPACName = Hydroquinone
|  ImageFile2 = Hydroquinone crystal.jpg
|  OtherNames = Quinol<br />Benzene-1,4-diol
|  IUPACName = Benzene-1,4-diol
|  OtherNames = Idrochinone<br />Quinol/1-4 dihydroxy benzene/1-4 hydroxy benzene
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
|  SMILES = Oc1ccc(O)cc1
|  ChEBI_Ref = {{ebicite|correct|EBI}}
|   CASNo = 123-31-9
| ChEBI = 17594
|   RTECS = MX3500000
| SMILES = c1cc(ccc1O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 764
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 537
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = XV74C1N1AE
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00073
| InChI = 1/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
| InChIKey = QIGBRXMKCJKVMJ-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QIGBRXMKCJKVMJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 123-31-9
| RTECS = MX3500000
| ATCCode_prefix = D11
| ATCCode_suffix = AX11
   }}
   }}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
|  Formula = C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub>
|  C=6
|  MolarMass = 110.1 g/mol
|  H=6
|  O=2
|  Appearance = white solid
|  Appearance = white solid
|  Density = 1.3 g/cm<sup>3</sup>, solid
|  Density = 1.3 g cm<sup>−3</sup>, solid
|  Solubility = 5.9 g/100 ml (15 °C)
|  Solubility = 5.9 g/100 mL (15 °C)
|  MeltingPt = 172 °C
|  MeltingPtC = 172
|  BoilingPt = 287 °C
|  BoilingPtC = 287
|  pKa =  
|  pKa =  
   }}
   }}
| Section3 = {{Chembox Structure
| Section3 = {{Chembox Structure
|  Dipole = zero
|  Dipole = 1.4 D
   }}
   }}
| Section7 = {{Chembox Hazards
| Section7 = {{Chembox Hazards
|  ExternalMSDS =
|  ExternalMSDS =
|  EUClass = Harmful ('''Xn''')<br />[[Carcinogen|Carc. Cat. 3]]<br />[[Mutagen|Muta. Cat. 3]]<br />Dangerous for<br />the environment ('''N''')
|  EUClass = Harmful ('''Xn''')<br />[[Carcinogen|Carc. Cat. 3]]<br />[[Mutagen|Muta. Cat. 3]]<br />Dangerous for<br />the environment ('''N''')
|  RPhrases = {{R22}}, {{R40}},
|  NFPA-H = 2
|  SPhrases = {{S2}}, {{S26}}, {{S36/37/39}}, {{S61}}
|  NFPA-F = 1
|  FlashPt = 165 °C
|  NFPA-R =
|  NFPA_Ref=<ref>http://assets.openstudy.com/updates/attachments/4f0d5cb6e4b084a815fccd72-chmvijay-1326448458607-dipolemoment.pdf</ref>
|  RPhrases = {{R22}} {{R40}} {{R41}} {{R43}} {{R50}} {{R68}}
|  SPhrases = {{S2}} {{S26}} {{S36/37/39}} {{S61}}
|  FlashPtC = 165
   }}
   }}
| Section8 = {{Chembox Related
| Section8 = {{Chembox Related
Line 36: Line 112:
   }}
   }}
}}
}}
{{SI}}
|mechAction=* Hydroquinone  acts by inhibiting the breakdown of tyrosine to 3-(3,4-dihydroxyphenyl) alanine (dopa) and thus suppresseing metabolic processes of melanocytes,  to produce depigmentation of the skin which is reversible
{{EH}}
|storage=* Store at room temperature (15-30°C / 59-86°F).
 
* Close cap securely after each use.
==Overview==
|alcohol=Alcohol-Hydroquinone interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
'''Hydroquinone''', also '''benzene-1,4-diol''' or '''quinol''', is an [[aromatic]] [[organic compound]] which is a type of [[Phenols|phenol]], having the [[chemical formula]] C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub>. Its [[chemical structure]], shown in the table at right, has two [[hydroxyl group]]s [[covalent bond|bonded]] to a [[benzene ring]] in a ''para'' position. It is a white granular [[solid]] at room [[temperature]] and [[pressure]].
|brandNames=ACTIVE 4
 
|nlmPatientInfo=(Link to patient information page)
==Nomenclature==
|drugShortage=Drug Shortage
Hydroquinone is the name recommended by the [[International Union of Pure and Applied Chemistry]] (IUPAC) in its ''1993 Recommendations for the Nomenclature of Organic Chemistry''.{{ref|BlueBook}}
}}
 
{{LabelImage
==Properties==
|fileName=Hydroquinone ingredients and appearance.png
Hydroquinone can undergo mild [[oxidation]] to convert to the compound ''parabenzoquinone'', C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>, often called ''p''-quinone or simply [[quinone]].  [[Redox|Reduction]] of quinone reverses this reaction back to hydroquinone. Some biochemical compounds in nature have this sort of hydroquinone or quinone section in their structures, such as [[Coenzyme Q]], and can undergo similar [[redox]] interconversions.
}}
 
{{LabelImage
The hydroxyl groups of hydroquinone are quite weakly [[acidic]]. Hydroquinone can lose an H<sup>+</sup> from one of the hydroxyls to form a monophenolate ion or lose an H<sup>+</sup> from both to form a diphenolate ion.
|fileName=Active 4.jpg
 
}}
==Uses==
Hydroquinone has a variety of uses principally associated with its action as a [[reducing agent]] which is [[soluble]] in water.  It is a major component in most photographic developers where, with the compound [[Metol]], it reduces silver [[halides]] to elemental [[silver]].
 
In human medicine, hydroquinone is used as a topical application in [[skin whitening]] to reduce the color of skin as it does not have the same predisposition to cause [[dermatitis]] as Metol does. This use is banned in some countries (e.g. France) because of fears of a [[cancer]] risk.
 
The di[[sodium]] diphenolate [[salt]] of hydroquinone is used as an alternating co[[monomer]] unit in the production of the [[polymer]] [[PEEK]].
 
As a polymerization inhibitor, hydroquinone prevents polymerization of acrylic acid, methyl methacrylate, etc.
 
It is also used as a raw material of herbicides, rubber antioxidants and dye stuffs.
 
==Natural occurrences==
Hydroquinones are one of the two primary reagents in the defensive glands of bombardier beetles, along with [[hydrogen peroxide]] (and perhaps other chemicals, depending on the species), which collect in a reservoir. The reservoir opens through a muscle-controlled valve onto a thick-walled reaction chamber. This chamber is lined with cells that secrete [[catalase]]s and [[peroxidase]]s. When the contents of the reservoir are forced into the reaction chamber, the catalases and peroxidases rapidly break down the hydrogen peroxide and [[catalysis|catalyze]] the [[oxidation]] of the hydroquinones into [[quinone|p-quinones]]. These reactions release free oxygen and generate enough heat to bring the mixture to the boiling point and vaporize about a fifth of it, producing a hot spray from the beetle's [[abdomen]].
 
==See also==
*[[Pyrocatechol]]
*[[Resorcinol]]
 
==References==
#{{note|BlueBook}} {{cite book | author=Panico, R.; & Powell, W. H. (Eds.) | title=A Guide to IUPAC Nomenclature of Organic Compounds 1993 | location=Oxford | publisher=Blackwell Science | year=1994 | id=ISBN 0-632-03488-2}}
 
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc01/icsc0166.htm International Chemical Safety Card 0166]
*[http://www.cdc.gov/niosh/npg/npgd0338.html NIOSH Pocket Guide to Chemical Hazards]
*[http://www-cie.iarc.fr/htdocs/monographs/vol71/024-hydroquinone.html IARC Monograph: "Hydroquinone"]
*{{ecb}}
*[http://www.acdlabs.com/iupac/nomenclature/ IUPAC Nomenclature of Organic Chemistry] (online version of the "''Blue Book''")
 
{{Other dermatological preparations}}
{{SIB}}
[[Category:Benzenediols]]
[[Category:Photographic chemicals]]
[[Category:IARC Group 3 carcinogens]]
 
{{jb1}}


{{WH}}
[[Category:Hydroquinones]]
{{WikiDoc Sources}}
[[Category:Drug]]

Latest revision as of 16:28, 20 August 2015

Hydroquinone
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Kiran Singh, M.D. [2]

Disclaimer

WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.

Overview

Hydroquinone is a dermatological agent that is FDA approved for the treatment of discoloration of skin, hyperpigmentation of skin. Common adverse reactions include burning sensation, contact dermatitis, localized erythema.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Indications

Dosing

  • Use fingertips to apply a thin layer to affected areas. Use both morning and night or as directed by a physician. Gradual lightening of the discolored area can be expected in most cases.

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Indications and Dosage

  • Discoloration of skin: emulsion, apply topically twice daily to affected area(s) or as directed by physician for no longer than 2 months.
  • Hyperpigmentation of skin: cream and gel, with or without sunscreens, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; rub in well.
  • Hyperpigmentation of skin: cream with sunblock, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; do not rub in.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Hydroquinone in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

There is limited information regarding Hydroquinone FDA-Labeled Indications and Dosage (Pediatric) in the drug label.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Indications and Dosage

  • Safety and efficacy not established in children less than 12 years of age; not recommended for use except under physician supervision.
  • Discoloration of skin: 12 years and older; emulsion, apply topically twice daily to affected area(s) or as directed by physician for no longer than 2 months.
  • Hyperpigmentation of skin: 12 years and older; cream and gel, with or without sunscreens, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; rub in well.
  • Hyperpigmentation of skin: 12 years and older; cream with sunblock, apply topically twice daily to the affected area(s) or as directed by physician for no longer than 2 months; do not rub in.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Hydroquinone in pediatric patients.

Contraindications

  • Hypersensitivity to hydroquinone or any component of hydroquinone products.
  • Pregnancy, safety not established.
  • Children 12 years of age and under; safety not established.

Warnings

There is limited information regarding Warnings of Hydroquinone in patients.

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Hydroquinone Clinical Trials Experience in the drug label.

Postmarketing Experience

Dermatologic: Burning sensation, contact dermatitis, localized erythema

Drug Interactions

There is limited information regarding Drug Interactions of Hydroquinone in patients.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA): There is no FDA guidance on usage of Hydroquinone in women who are pregnant.
Pregnancy Category (AUS): There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Hydroquinone in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Hydroquinone during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Hydroquinone in women who are nursing.

Pediatric Use

There is no FDA guidance on the use of Hydroquinone in pediatric settings.

Geriatic Use

There is no FDA guidance on the use of Hydroquinone in geriatric settings.

Gender

There is no FDA guidance on the use of Hydroquinone with respect to specific gender populations.

Race

There is no FDA guidance on the use of Hydroquinone with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Hydroquinone in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Hydroquinone in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Hydroquinone in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Hydroquinone in patients who are immunocompromised.

Others

Administration and Monitoring

Administration

Topical

  • Avoid exposure of treated areas to sunlight.
  • Avoid contact with eyes.

Monitoring

  • Repigmentation

IV Compatibility

There is limited information regarding IV Compatibility of Hydroquinone in patients.

Overdosage

There is limited information regarding Overdose of Hydroquinone in patients.

Pharmacology

Template:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox entryTemplate:Chembox E numberTemplate:Chembox RTECSTemplate:Chembox AppearanceTemplate:Chembox DensityTemplate:Chembox MeltingPtTemplate:Chembox BoilingPtTemplate:Chembox SolubilityInWaterTemplate:Chembox StructureTemplate:Chembox EUClassTemplate:Chembox RPhrasesTemplate:Chembox SPhrasesTemplate:Chembox NFPATemplate:Chembox FlashPtTemplate:Chembox Supplement
Template:Chembox header2 | Hydroquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
Properties
C6H6O2
Molar mass 110.11 g·mol−1
Hazards
Related compounds
Template:Chembox header2 | Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Mechanism of Action

  • Hydroquinone acts by inhibiting the breakdown of tyrosine to 3-(3,4-dihydroxyphenyl) alanine (dopa) and thus suppresseing metabolic processes of melanocytes, to produce depigmentation of the skin which is reversible

Structure

There is limited information regarding Hydroquinone Structure in the drug label.

Pharmacodynamics

There is limited information regarding Hydroquinone Pharmacodynamics in the drug label.

Pharmacokinetics

There is limited information regarding Hydroquinone Pharmacokinetics in the drug label.

Nonclinical Toxicology

There is limited information regarding Hydroquinone Nonclinical Toxicology in the drug label.

Clinical Studies

There is limited information regarding Hydroquinone Clinical Studies in the drug label.

How Supplied

There is limited information regarding Hydroquinone How Supplied in the drug label.

Storage

  • Store at room temperature (15-30°C / 59-86°F).
  • Close cap securely after each use.

Images

Drug Images

{{#ask: Page Name::Hydroquinone |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Hydroquinone |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Hydroquinone Patient Counseling Information in the drug label.

Precautions with Alcohol

Alcohol-Hydroquinone interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

ACTIVE 4

Look-Alike Drug Names

There is limited information regarding Hydroquinone Look-Alike Drug Names in the drug label.

Drug Shortage Status

Drug Shortage

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ http://assets.openstudy.com/updates/attachments/4f0d5cb6e4b084a815fccd72-chmvijay-1326448458607-dipolemoment.pdf

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 |Label Name=Hydroquinone ingredients and appearance.png

}}

{{#subobject: 

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 |Label Name=Active 4.jpg

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