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
==Overview==
===Chronic Overdose===
'''Salicylic acid''' (from the Latin word for the willow tree, ''[[Salix]]'', from whose bark it can be obtained) is a [[beta hydroxy acid]] (BHA) with the [[chemical formula|formula]] C<sub>6</sub>H<sub>4</sub>(OH)CO<sub>2</sub>H, where the OH group is adjacent to the [[carboxylic acid|carboxyl group]]. This colorless crystalline organic [[acid]] is widely used in [[organic synthesis]] and functions as a [[plant hormone]]. It is derived from the metabolism of [[salicin]]. It is probably best known as a compound that is chemically similar but not identical to the active component of [[aspirin]].
==Production==
There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
Salicylic acid is [[biosynthesis|biosynthesize]]d from the amino acid [[phenylalanine]].
[[Sodium salicylate]] is commercially prepared by treating sodium [[phenol|phenoxide]] with a high pressure of [[carbon dioxide]] at high temperature via the [[Kolbe-Schmitt reaction]]. Acidification of the product solution gives salicylic acid:
It can be prepared by the [[hydrolysis]] of [[Aspirin]] (acetylsalicylic acid)<ref>{{cite web | title=Hydrolysis of ASA to SA | url=http://www.crscientific.com/article-aspirin.html | accessdate=July 31 | accessyear=2007 }}</ref> or [[methyl salicylate]] (Oil of Wintergreen) with a strong acid or base.
<!--Structure-->
|structure=*
==Analysis==
: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]
Salicylic acid is an [[enol]] of an β-ketocarbonic acid and therefore forms purple complexes with iron(III) salts:
[[Image:Betaketocarbonicacid iron complex.png|600px]]
This tris(chelate) complex forms more readily in basic solution.
<!--Pharmacodynamics-->
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.
==History==
<!--Pharmacokinetics-->
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.
The Greek physician [[Hippocrates]] wrote in the 5th century BC about a bitter powder extracted from [[willow]] bark that could ease aches and pains and reduce fevers. This remedy was also mentioned in texts from ancient Sumer, Lebanon, and Assyria. The Cherokee and other Native Americans used an infusion of the bark for fever and other medicinal purposes for centuries.<ref>Paul B. Hemel and Mary U. Chiltoskey, ''Cherokee Plants and Their Uses -- A 400 Year History,'' Sylva, NC: Herald Publishing Co. (1975); cited in Dan Moerman, A Database of Foods, Drugs, Dyes and Fibers of Native American Peoples, Derived from Plants.[http://herb.umd.umich.edu/] A search of this database for "salix AND medicine" finds 63 entries.</ref> The medicinal part of the plant is the inner bark and was used as a pain reliever for a variety of ailments. The [[Reverend Edward (Edmund) Stone]], a vicar from Chipping Norton, Oxfordshire, England, noted in 1763 that the bark of the willow was effective in reducing a fever.<ref name="RoyalSoc1763EdmundStone">{{cite journal | author=Stone, E | title=An Account of the Success of the Bark of the Willow in the Cure of Agues | journal=Philosophical Transactions | year=1763 | pages=195–200 | volume=53 | url=http://www.journals.royalsoc.ac.uk/openurl.asp?genre=article&issn=0260-7085&volume=53&spage=195}}</ref>
<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.
The active extract of the bark, called ''[[salicin]]'', after the [[Latin]] name for the white willow (''Salix alba''), was isolated in crystalline form in 1828 by Henri Leroux, a French pharmacist, and Raffaele Piria, an Italian chemist. Piria was able to convert the substance into a sugar and a second component, which on oxidation becomes [[salicylic acid]].
<!--Clinical Studies-->
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.
Salicylic acid was also isolated from the herb [[meadowsweet]] (''Filipendula ulmaria'', formerly classified as ''Spiraea ulmaria'') by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as [[gastric]] irritation, bleeding, [[diarrhea]], and even death when consumed in high doses.
<!--How Supplied-->
|howSupplied=*
==Medicinal and cosmetic uses==
<!--Patient Counseling Information-->
Also known as 2-hydroxybenzoic acid, one of several beta hydroxy acids (compare to [[Alpha hydroxy acid|AHA]]), salicylic acid is a key ingredient in many skin-care products for the treatment of [[Acne vulgaris|acne]], [[psoriasis]], [[callus]]es, [[callus|corns]], [[keratosis pilaris]], and [[wart]]s. It works by causing the cells of the [[Epidermis (skin)|epidermis]] to slough off more readily, preventing [[sebaceous gland|pores]] from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several [[shampoo]]s used to treat [[dandruff]]. Salicylic acid is also used as an active ingredient in gels which remove [[verrucas]] (plantar warts). Use of concentrated solutions of salicylic acid may cause [[hyperpigmentation]] on unpretreated skin for those with darker skin types ([[Fitzpatrick scale|Fitzpatrick]] phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock.<ref>{{cite journal|title=The Safety and Efficacy of Salicylic Acid Chemical Peels in Darker Racial-ethnic Groups| author= Grimes P.E.|journal= Dermatologic Surgery| volume= 25|year= 1999| pages =18–22}}</ref><ref>{{cite journal|title= Chemical peeling in ethnic/dark skin| author= Roberts W. E. |journal=Dermatologic Therapy |volume= 17|issue= 2| pages= 196|year= 2004|doi= 10.1111/j.1396-0296.2004.04020.x}}</ref>
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.
The medicinal properties of salicylate, mainly for [[fever]] relief, have been known since ancient times, and it was used as an anti-inflammatory drug.<ref>{{cite journal|title=Brief History of Antipyretic Therapy|author=Philip A. Mackowiak|journal=Clinical Infectious Diseases,| volume= 31|year=2000 |pages= 154–156|doi= 10.1086/317510}}</ref>
<!--Precautions with Alcohol-->
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
[[Image:Salicylic acid pads.jpg|thumb|right|[[Cotton]] pads soaked in salicylic acid can be used to chemically [[Exfoliation (cosmetology)|exfoliate]] skin]]
<!--Brand Names-->
[[Aspirin]] (acetylsalicylic acid or ASA) can be prepared by the [[esterification]] of the phenolic hydroxyl group of salicylic acid.
|brandNames=* ®<ref>{{Cite web | title = | url = }}</ref>
Subsalicylate in combination with [[bismuth]] form the popular stomach relief aid known commonly as [[Bismuth subsalicylate|Pepto-Bismol]]. When combined, the two key ingredients help control [[diarrhea]], nausea, heartburn, and gas. It is also a very mild [[antibiotic]].
<!--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>
==Safety==
<!--Drug Shortage Status-->
Salicylic acid has an [[ototoxic]] effect, and can induce transient hearing loss in [[zinc]]-deficient individuals.
|drugShortage=
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|fileName={{PAGENAME}}11.png
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{{LabelImage
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<!--Pill Image-->
This finding is based on clinical studies with rats. An injection of salicylic acid induced hearing loss in zinc-deficient rats, while a simultaneous injection of zinc reversed the hearing loss. An injection of [[magnesium]] in the zinc-deficient rats did not reverse the salicylic acid-induced hearing loss.
Salicylic acid is toxic in large amounts. Pregnant women are advised not to use products containing salicylic acid due to the danger of [[Reye's syndrome]].
Some people are [[Salicylate sensitivity|hypersensitive to salicylic acid and related compounds]].
<!--Label Display Image-->
The United States [[Food and Drug Administration]] recommends the use of sun protection when using skincare products containing salicylic acid (or any other BHA) on sun-exposed skin areas. <ref>{{cite web |url=http://www.cfsan.fda.gov/~dms/cos-bha.html|title=Beta Hydroxy Acids in Cosmetics |accessdate=2007-11-23 |format= |work=}}</ref>
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Black Box Warning
ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
Content
Overview
Salicylic acid 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
Dosage
Condition4
Dosing Information
Dosage
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 Salicylic acid in adult patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Salicylic acid 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 Salicylic acid 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 Salicylic acid in pediatric patients.
Non–Guideline-Supported Use
Condition1
Dosing Information
Dosage
Condition2
There is limited information regarding Off-Label Non–Guideline-Supported Use of Salicylic acid 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 Salicylic acid 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 Salicylic acid in the drug label.
