There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
<!--Non–Guideline-Supported Use (Adult)-->
|offLabelAdultNoGuideSupport======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
<!--Pediatric Indications and Dosage-->
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>FDA-Labeled Use</i> of {{PAGENAME}} in pediatric patients.
<!--Off-Label Use and Dosage (Pediatric)-->
<!--Guideline-Supported Use (Pediatric)-->
|offLabelPedGuideSupport======Condition1=====
* Developed by:
* Class of Recommendation:
* Strength of Evidence:
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport======Condition1=====
* Dosing Information
:* Dosage
=====Condition2=====
There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
<!--Contraindications-->
|contraindications=* Condition1
<!--Warnings-->
|warnings=* Description
====Precautions====
* Description
<!--Adverse Reactions-->
<!--Clinical Trials Experience-->
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
=====Body as a Whole=====
=====Cardiovascular=====
=====Digestive=====
=====Endocrine=====
=====Hematologic and Lymphatic=====
=====Metabolic and Nutritional=====
=====Musculoskeletal=====
=====Neurologic=====
=====Respiratory=====
=====Skin and Hypersensitivy Reactions=====
=====Special Senses=====
=====Urogenital=====
=====Miscellaneous=====
<!--Postmarketing Experience-->
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
=====Body as a Whole=====
=====Cardiovascular=====
=====Digestive=====
=====Endocrine=====
=====Hematologic and Lymphatic=====
=====Metabolic and Nutritional=====
=====Musculoskeletal=====
=====Neurologic=====
=====Respiratory=====
=====Skin and Hypersensitivy Reactions=====
=====Special Senses=====
=====Urogenital=====
=====Miscellaneous=====
<!--Drug Interactions-->
|drugInteractions=* Drug
:* Description
<!--Use in Specific Populations-->
|useInPregnancyFDA=* '''Pregnancy Category'''
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''
There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of {{PAGENAME}} in women who are pregnant.
|useInLaborDelivery=There is no FDA guidance on use of {{PAGENAME}} during labor and delivery.
|useInNursing=There is no FDA guidance on the use of {{PAGENAME}} with respect to nursing mothers.
|useInPed=There is no FDA guidance on the use of {{PAGENAME}} with respect to pediatric patients.
|useInGeri=There is no FDA guidance on the use of {{PAGENAME}} with respect to geriatric patients.
|useInGender=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with renal impairment.
|useInHepaticImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with hepatic impairment.
|useInReproPotential=There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.
<!--Administration and Monitoring-->
|administration=* Oral
* Intravenous
|monitoring=There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
* Description
<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.
<!--Overdosage-->
|overdose====Acute Overdose===
====Signs and Symptoms====
* Description
====Management====
* Description
===Chronic Overdose===
There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
<!--Pharmacology-->
<!--Drug box 2-->
|drugBox=<!--Mechanism of Action-->
|mechAction=*
==Overview==
<!--Structure-->
'''Resorcinol''' (or '''resorcin''') is a [[chemical compound]] from the dihydroxy [[phenol]]s. it is the 1,3-[[isomer]] of [[benzenediol]]. It is also known with a variety of other names, including: m-dihydroxybenzene, 1,3-benzenediol, 1,3-dihydroxybenzene, 3-hydroxyphenol, m-hydroquinone, m-benzenediol, and 3-hydroxycyclohexadien-1-one.
|structure=*
==Nomenclature==
: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]
Resorcinol 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}}
==Production==
<!--Pharmacodynamics-->
It is obtained on fusing many [[resin]]s ([[galbanum]], [[asafoetida]], etc.) with [[potassium hydroxide]], or by the [[distillation]] of [[Brazilwood]] extract. It may be prepared [[organic synthesis|synthetically]] by fusing [[3-Iodophenol|3-iodophenol]], [[phenol-3-sulfonic acid]] or [[benzene-1,3-disulfonic acid]] with [[potassium carbonate]]; by the action of [[nitrous acid]] on [[3-Aminophenol|3-aminophenol]]; or by the action of 10% [[hydrochloric acid]] on [[1,3-diaminobenzene]] (J. Meyer, Ber., 1897, 30, p. 2569). Many ''ortho''- and ''para''-compounds of the [[aromatic]] series (for example, the bromophenols, benzene-''para''-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide. also is a two ball screw ball.
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.
==Properties==
<!--Pharmacokinetics-->
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.
Resorcinol crystallizes from [[benzene]] as colorless needles which are readily soluble in water, alcohol and ether, but insoluble in [[chloroform]] and [[carbon disulfide]]. It reduces [[Fehling's solution]], and [[Tollens' reagent|ammoniacal silver solutions]]. It does not form a precipitate with [[lead acetate]] solution, as the isomeric [[pyrocatechol]] does. [[Iron(III) chloride]] colors its aqueous solution a dark violet, and [[bromine]] water precipitates tribromoresorcin. [[Sodium amalgam]] reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated [[barium hydroxide]] solution gives γ-acetylbutyric acid (D. Vorlgnder); when fused with potassium hydroxide, resorcinol yields [[phloroglucin]], pyrocatechol and [[diresorcin]]. It [[condensation reaction|condenses]] with [[acid]]s or [[acid chloride]]s, in the presence of dehydrating agents, to oxyketones, e.g. with [[zinc chloride]] and glacial [[acetic acid]] at 145 °C it yields resacetophenone (HO)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>~CO.CH<sub>3</sub>(M. Nencki and N. Sieber, Jour. prak. Chem., 1881, 23, p. 147). With the [[anhydride]]s of dibasic acids it yields [[fluorescein]]s. When heated with [[calcium chloride]]—[[ammonia]] to 200 °C it yields meta-dioxydiphenylamine (A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811). With [[sodium nitrite]] it forms a water-soluble blue dye, which is turned red by acids, and is used as an [[indicator]], under the name of lacmoid (M. C. Traub and C. Hock, Ber., 1884, 17, p. 2615). It condenses readily with [[aldehyde]]s, yielding with [[formaldehyde]], on the addition of catalytic [[hydrochloric acid]], methylene diresorcin [(HO)C<sub>6</sub>H<sub>3</sub>(O)]<sub>2</sub>•CH<sub>2</sub>, whilst with [[chloral hydrate]], in the presence of [[Potassium hydrogensulfate|potassium bisulfate]], it yields the [[lactone]] of tetra-oxydiphenyl methane carboxylic acid (J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084). In alcoholic solution it condenses with [[sodium acetoacetate]] to form 13-methylumbelliferone, C~OH<sub>8</sub>O<sub>3</sub> (A. Michael, Jour. prak. Chem., 1888, 37, 470).
<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.
With concentrated [[nitric acid]], in the presence of cold concentrated [[sulfuric acid]], it yields trinitro-resorcin ([[styphnic acid]]), which forms yellow crystals, exploding violently on rapid heating.
<!--Clinical Studies-->
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.
==Applications==
<!--How Supplied-->
===Medical===
|howSupplied=*
Used externally it is an [[antiseptic]] and [[disinfectant]], and is used 5 to 10% in ointments in the treatment of chronic skin diseases such as [[psoriasis]] and [[eczema]] of a sub-acute character. It is present in over-the-counter topical acne treatments at 2% concentration, and in prescription treatments at higher concentrations. Weak, watery solutions of resorcinol (10 or 15 [[grain (unit)|grains]] to the ounce, or 25 to 35 g/kg) are useful in allaying the itching in erythematous eczema. A 2% solution used as a spray has been used with marked effect in [[hay fever]] and in [[whooping cough]]. In the latter disease 0.6 mL of the 2% solution has been given internally. It can be included as an anti-dandruff agent in shampoo or in sunscreen cosmetics. It has also been employed in the treatment of gastric ulcer in doses of 125 to 250 mg in pills, and is said to be analgesic and haemostatic in its action. In large doses it is a poison causing giddiness, deafness, salivation, sweating and convulsions. It is also worked up in certain medicated soaps. Monoacetylresorcinol, C<sub>6</sub>H<sub>4</sub>(OH)(O-COCH<sub>3</sub>), is used under the name of '''euresol'''.
|packLabel=<!--Patient Counseling Information-->
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.
===Chemical===
<!--Precautions with Alcohol-->
Resorcinol is also used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of diazo dyes and plasticizers and as a [[UV]] absorber in resins.
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
An emerging use of resorcinol is as a template molecule in [[supramolecular chemistry]]. The -OH groups on resorcinol form [[hydrogen bond]]s to target molecules holding them in the proper orientation for a reaction. Many such reactions are able to be carried out in the [[Phase (matter)|solid state]] thereby reducing or eliminating the use of solvents that may be harmful to the environment. (see [[Green chemistry]])
<!--Brand Names-->
|brandNames=* ®<ref>{{Cite web | title = | url = }}</ref>
Resorcinol is an analytical reagent for the qualitative determinaion of ketoses ([[Seliwanoff's test]]).
<!--Look-Alike Drug Names-->
|lookAlike=* A® — B®<ref name="www.ismp.org">{{Cite web | last = | first = | title = http://www.ismp.org | url = http://www.ismp.org | publisher = | date = }}</ref>
Resorcinol is the starting material for [[resorcinarene]] molecules.
<!--Drug Shortage Status-->
|drugShortage=
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<!--Pill Image-->
==Related compounds==
Resazurin, C<sub>12</sub>H<sub>7</sub>NO<sub>4</sub>, obtained by the action of nitrous acid on resorcinol (P. Weselsky and R. Benedikt, Monats., 1880, f, p. 889), forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated sulphuric acid and warmed to 210 °C, the solution on pouring into water yields a precipitate of resorufin, C<sub>12</sub>H<sub>7</sub>NO<sub>3</sub>, an oxyphenoxazone, which is insoluble in water, but is readily soluble in hot concentrated hydrochloric acid, and in solutions of caustic alkalis. The alkaline solutions are of a rose-red color and show a cinnabar-red fluorescence. A tetrabromresorufin is used as a dye-stuff under the name of Fluorescent Resorcin Blue.
Thioresorcinol is obtained by the action of zinc and hydrochloric acid on the chloride of benzene meta-disulphonic acid. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid (HO)<sub>2</sub>C<sub>6</sub>H<sub>2</sub>(HSO3)<sub>2</sub>, is a deliquescent mass obtained by the action of sulphuric acid on resorcin (H. Fischer, Monats., 1881, 2, p. 321). It is easily soluble in water and decomposes when heated to 100 °C.
==Reference==
<!--Label Display Image-->
#{{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}}
==References==
<references/>
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1033.htm International Chemical Safety Card 1033]
*[http://www.cdc.gov/niosh/npg/npgd0543.html NIOSH Pocket Guide to Chemical Hazards]
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Black Box Warning
ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
Content
Overview
Resorcinol is a {{{drugClass}}} that is FDA approved for the {{{indicationType}}} of {{{indication}}}. There is a Black Box Warning for this drug as shown here. Common adverse reactions include .
Adult Indications and Dosage
FDA-Labeled Indications and Dosage (Adult)
Condition1
Dosing Information
Dosage
Condition2
Dosing Information
Dosage
Condition3
Dosing Information
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Condition4
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Off-Label Use and Dosage (Adult)
Guideline-Supported Use
Condition1
Developed by:
Class of Recommendation:
Strength of Evidence:
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Guideline-Supported Use of Resorcinol in adult patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Resorcinol in adult patients.
Pediatric Indications and Dosage
FDA-Labeled Indications and Dosage (Pediatric)
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding FDA-Labeled Use of Resorcinol in pediatric patients.
Off-Label Use and Dosage (Pediatric)
Guideline-Supported Use
Condition1
Developed by:
Class of Recommendation:
Strength of Evidence:
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Guideline-Supported Use of Resorcinol in pediatric patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Resorcinol in pediatric patients.
Contraindications
Condition1
Warnings
ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
Content
Description
Precautions
Description
Adverse Reactions
Clinical Trials Experience
There is limited information regarding Clinical Trial Experience of Resorcinol in the drug label.
Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous
Postmarketing Experience
There is limited information regarding Postmarketing Experience of Resorcinol in the drug label.
