Salicylic acid: Difference between revisions

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{{Chembox new
{{DrugProjectFormSinglePage
|   Name = Salicylic acid
|authorTag={{Ammu}}
|  ImageFile = Salicylic-acid-skeletal.svg
|genericName=Salicylic acid
|  ImageFile1 = Salicylic-acid-3D-vdW.png
|aOrAn=an
|  IUPACName = 2-Hydroxybenzoic acid
|drugClass=anti [[acne]] agent
| Section1 = {{Chembox Identifiers
|indicationType=treatment
|  CASNo = 69-72-7
|indication=[[acne]], for relief of [[itching]], irritation, [[redness]] and scaling assoicated with [[psoriasis]], [[eczema]] and [[seborrheic dermatitis]]
|  EINECS = 200-712-3
|adverseReactions=[[hypersensitivity]] reaction, salicylate toxicity
|  SMILES = OC(=O)c1ccccc1O
|blackBoxWarningTitle=<span style="color:#FF0000;">ConditionName: </span>
  }}
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>
| Section2 = {{Chembox Properties
|   Formula = C<sub>7</sub>H<sub>6</sub>O<sub>3</sub>
|   MolarMass = 138.123 g/mol
|  MeltingPt = 159 °C
|  BoilingPt = 211 °C (2666 Pa)
|   Density = 1.44 g/cm³ (at 20 °C)
  }}
| Section8 = {{Chembox Related
|  OtherCpds = [[Methyl salicylate]],<br/>[[Benzoic acid]],<br/>[[Phenol]], [[Aspirin]],<br/>[[4-Hydroxybenzoic acid]],<br/> [[Magnesium salicylate]],<br/>[[Bismuth subsalicylate|Bismuth subsalicylate (Pepto Bismol)]],<br/>[[Sulfosalicylic acid]]
  }}
}}
{{CMG}}


==Overview==
* Content
'''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==
<!--Adult Indications and Dosage-->
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:
<!--FDA-Labeled Indications and Dosage (Adult)-->
|fdaLIADAdult=* FOR THE TREATMENT OF ACNE
* HELPS KEEP SKIN CLEAR OF NEW ACNE BLEMISHES
* For relief of itching, irritation, redness and scaling assoicated with [[psoriasis]], [[eczema]] and [[seborrheic dermatitis]].
|offLabelAdultGuideSupport=* [[Acne vulgaris]]
:* Apply TOPICALLY in concentrations of 0.5% to 10%
:* Disorder of skin, Hyperkeratotic: gel, apply TOPICALLY to the affected area and occlude the area at night.
* Disorder of skin, Hyperkeratotic
:* shampoo, wet hair and apply TOPICALLY to the scalp, work into a lather and rinse; repeat the treatment as needed until the condition clears [5]
* Psoriasis
:* Apply TOPICALLY in concentrations of 3% to 6%
* Removal of wart
:* Apply TOPICALLY once or twice daily in concentrations of 5% to 40% for up to 12 weeks
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.


:[[Image:Kolbe-Schmitt.png|left|400px]]<br clear=left/>
<!--Pediatric Indications and Dosage-->


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.
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed=There is limited information regarding <i>FDA-labeled indications and dosage information</i> of {{PAGENAME}} in pediatric patients.
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.


==Analysis==
<!--Non–Guideline-Supported Use (Pediatric)-->
Salicylic acid is an [[enol]] of an &beta;-ketocarbonic acid and therefore forms purple complexes with iron(III) salts:
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
[[Image:Betaketocarbonicacid iron complex.png|600px]]


This tris(chelate) complex forms more readily in basic solution.
<!--Contraindications-->
|warnings=* For external use only.
* Avoid contact with eyes. If contact occurs, rinse thoroughly with water.
* Do not use without consulting a doctor if the condition appears over a large portion of hte body.
* If condition worsens, or does not improve after using as directed, consult physician.
* Do not use for prolonged periods without consulting a doctor.
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
|useInPregnancyFDA=* '''Pregnancy Category'''
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''


==History==
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.


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>
<!--Administration and Monitoring-->
|administration=* Topical
|monitoring=There is limited information regarding <i>Monitoring</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]].


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.
<!--IV Compatibility-->
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.


==Medicinal and cosmetic uses==
<!--Overdosage-->
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>
|overdose=There is limited information regarding <i>Chronic Overdose</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>
<!--Pharmacology-->


[[Image:Salicylic acid pads.jpg|thumb|right|[[Cotton]] pads soaked in salicylic acid can be used to chemically [[Exfoliation (cosmetology)|exfoliate]] skin]]
<!--Drug box 2-->
[[Aspirin]] (acetylsalicylic acid or ASA) can be prepared by the [[esterification]] of the phenolic hydroxyl group of salicylic acid.
|drugBox={{chembox2
| Watchedfields = changed
| verifiedrevid = 477314005
| Name = Salicylic acid
| ImageFileL1 = Salicylic-acid-skeletal.svg
| ImageSizeL1 = 100px
| ImageNameL1 = Skeletal formula of salicylic acid
| ImageFileR1 = Salicylic-acid-from-xtal-2006-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of salicylic acid
| ImageFile2 = Kwas salicylowy.jpg
| ImageSize2 = 200px
| ImageName2 = Salicylic acid
| IUPACName = 2-Hydroxybenzoic acid
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O414PZ4LPZ
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00097
| InChI = 1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
| InChIKey = YGSDEFSMJLZEOE-UHFFFAOYAQ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 424
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YGSDEFSMJLZEOE-UHFFFAOYSA-N
| CASNo = 69-72-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 338
| EINECS = 200-712-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 331
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00936
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16914
| SMILES = c1ccc(c(c1)C(=O)O)O
| ATCCode_prefix = A01
| ATCCode_suffix = AD05
| ATC_Supplemental = {{ATC|B01|AC06}} {{ATC|D01|AE12}} {{ATC|N02|BA01}} {{ATC|S01|BC08}}
| RTECS = VO0525000
}}
| Section2 = {{Chembox Properties
| C=7|H=6|O=3
| Appearance = colorless to white crystals
| Odor = odorless
| MeltingPtC = 158.6
| BoilingPtC = 200
| Boiling_notes = <br> decomposes<ref name=chemister /><br> {{convert|211|C|F K}}<br> at 20 mmHg<ref name=crc>{{RubberBible92nd|page=3.306}}</ref>
| pKa = 1 = 2.97 (25 °C)<ref>[http://www.drugbank.ca/drugs/DB00936 Salicyclic acid]. Drugbank.ca. Retrieved on 2012-06-03.</ref><br> 2 = 13.82 (20 °C)<ref name=chemister />
| Density = 1.443 g/cm<sup>3</sup> (20 °C)<ref name=crc/>
| Solubility = 1.24 g/L (0 °C)<br> 2.48 g/L (25 °C)<br> 4.14 g/L (40 °C)<br> 17.41 g/L (75 °C)<ref name=chemister>http://chemister.ru/Database/properties-en.php?dbid=1&id=1777</ref><br> 77.79 g/L (100 °C)<ref name=sioc>{{cite book|last = Seidell|first = Atherton|last2 = Linke|first2 = William F.|year = 1952|title = Solubilities of Inorganic and Organic Compounds|publisher = Van Nostrand|url = [http://books.google.com/books?id=k2e5AAAAIAAJ Google Books]|accessdate = 2014-05-29}}</ref>
| SolubleOther = soluble in [[ether]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[benzene]], [[propanol]], [[acetone]], [[ethanol]], [[oil of turpentine]], [[toluene]]
| Solubility1 = 0.46 g/100 g (11.7 °C)<br> 0.775 g/100 g (25 °C)<br> 0.991 g/100 g (30.5 °C)<br> 2.38 g/100 g (49.4 °C)<br> 4.4 g/100 g (64.2 °C)<ref name=chemister /><ref name=sioc />
| Solvent1 = benzene
| Solubility2 = 2.22 g/100 mL (25 °C)<ref name=sioc /><br> 2.31 g/100 mL (30.5 °C)<ref name=chemister />
| Solvent2 = chloroform
| Solubility3 = 40.67 g/100 g (−3 °C)<br> 62.48 g/100 g (21 °C)<ref name=chemister />
| Solvent3 = methanol
| Solubility4 = 2.43 g/100 g (23 °C)<ref name=chemister />
| Solvent4 = olive oil
| Solubility5 = 39.6 g/100 g (23 °C)<ref name=chemister />
| Solvent5 = acetone
| RefractIndex = 1.565 (20 °C)<ref name=crc/>
| LogP = 2.26
| VaporPressure = 10.93 mPa<ref name=pubchem>{{PubChemLink|338}}</ref>
| SublimationConditions = sublimes at 76 °C<ref name=pubchem />
| LambdaMax = 210 nm, 234 nm, 303 nm (4&nbsp;mg % in ethanol)<ref name=pubchem />
}}
| Section5 = {{Chembox Thermochemistry
| DeltaHf = -589.9 kJ/mol
| DeltaHc = 3.025 MJ/mol<ref name=NIST>http://webbook.nist.gov/cgi/cbook.cgi?ID=C69727&Type=HCOMBS</ref>
}}
| Section8 = {{Chembox Related
| OtherCpds = [[Methyl salicylate]],<br />[[Benzoic acid]],<br />[[Phenol]], [[Aspirin]],<br />[[4-Hydroxybenzoic acid]],<br /> [[Magnesium salicylate]],<br />[[Choline salicylate]],<br />[[Bismuth subsalicylate]],<br />[[Sulfosalicylic acid]]
}}
| Section6 = {{Chembox Hazards
| ExternalMSDS = [http://avogadro.chem.iastate.edu/MSDS/salicylic_acid.htm MSDS]
| GHSPictograms = {{GHS05}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=w398500|name=Salicylic acid|accessdate=2014-05-23}}</ref>
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|318}}<ref name="sigma" />
| PPhrases = {{P-phrases|280|305+351+338}}<ref name="sigma" />
| RPhrases = {{R22}}, {{R38}}, {{R41}}, {{R61}}
| SPhrases = {{S22}}, {{S26}}, {{S36}}, {{S37}}, {{S39}}
| EUClass = {{Hazchem Xn}}
| EUIndex = 200-712-3
| MainHazards =
| SkinHazard = Mild irritation
| EyeHazard = Severe irritation
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPtC = 157
| Flash_notes = <br> closed cup<ref name=pubchem />
| AutoignitionPtC = 540
| Autoignition_ref = <ref name=pubchem />
| ExploLimits =
| PEL =
| LD50 = 480 mg/kg (mice, oral)
}}
}}
|mechAction=* Salicylic acid has been shown to work through several different pathways. It produces its anti-inflammatory effects via suppressing the activity of cyclooxygenase (COX), an enzyme that is responsible for the production of pro-inflammatory mediators such as the prostaglandins.
* It does this not by direct inhibition of COX like most other non-steroidal anti-inflammatory drugs (NSAIDs) but instead by suppression of the expression of the enzyme (via a yet-unelucidated mechanism).<ref name=American chemical society>{{cite web | title = American chemical society | url =http://www.cas.org/news/insights/science-connections/aspirin}}</ref>
* Salicylic acid has also been shown to activate adenosine monophosphate-activated protein kinase (AMPK), and it is thought that this action may play a role in the anticancer effects of the compound and its prodrugs aspirin and salsalate. In addition, the antidiabetic effects of salicylic acid are likely mediated by AMPK activation primarily through allosteric conformational change that increases levels of phosphorylation.<ref name="pmidPMID 22517326">{{cite journal| author=Hawley SA, Fullerton MD, Ross FA, Schertzer JD, Chevtzoff C, Walker KJ et al.| title=The ancient drug salicylate directly activates AMP-activated protein kinase. | journal=Science | year= 2012 | volume= 336 | issue= 6083 | pages= 918-22 | pmid=PMID 22517326 | doi=10.1126/science.1215327 | pmc=PMC3399766 | url=http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=22517326  }} </ref>
* Salicylic acid also uncouples oxidative phosphorylation, which leads to increased ADP:ATP and AMP:ATP ratios in the cell. As a consequence, salicylic acid may alter AMPK activity and subsequently exert its anti-diabetic properties through altered energy status of the cell. Even in AMPK knock-out mice, however, there is an anti-diabetic effect, demonstrating that there is at least one additional, yet-unidentified action of the compound.
<ref name=Newscientist>{{cite web | title = Newscientist | url =http://www.newscientist.com/article/dn21718-clues-to-aspirins-anticancer-effects-revealed.html }}</ref>
|structure=<!--Pharmacodynamics-->
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.


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]].
<!--Pharmacokinetics-->
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.


==Safety==
<!--Nonclinical Toxicology-->
Salicylic acid has an [[ototoxic]] effect, and can induce transient hearing loss in [[zinc]]-deficient individuals.
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.


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.  
<!--Clinical Studies-->
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.


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]].  
<!--How Supplied-->
|howSupplied=<!--Patient Counseling Information-->
|fdaPatientInfo=* Wash affected areas well with soap and water. Pat dry. Apply cream to affected area one to four times per day, or as directed by physician.
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


Some people are [[Salicylate sensitivity|hypersensitive to salicylic acid and related compounds]].  
<!--Brand Names-->
|brandNames=* ALA-SEPTIC®<ref>{{Cite web | title =ALA-SEPTIC- salicylic acid cream  | url =http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=edb70750-bea8-4c0f-9453-f2c38d2f05d9  }}</ref>
|drugShortage=
}}
{{LabelImage
|fileName=Saly 1.jpg
}}
{{LabelImage
|fileName=Saly 2.png
}}
{{LabelImage
|fileName=Saly 3.png
}}
{{LabelImage
|fileName=Saly 4.png
}}
<!--Pill Image-->
 
 
 
<!--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>


==Footnotes==
<div class="references-small">
<references />
</div>


{{Acne Agents}}
{{Ancient anaesthesia-footer}}
{{Antifungals}}
{{NSAIDs}}
{{Plant_hormones}}


[[Category:Antiseptics]]
[[Category:Benzoic acids]]
[[Category:Dermatological preparations]]
[[Category:Hydroxy acids]]
[[Category:Keratolytics]]
[[Category:Phenols]]


[[bg:Салицилова киселина]]
<!--Category-->
[[da:Salicylsyre]]
[[de:Salicylsäure]]
[[es:Ácido salicílico]]
[[fr:Acide salicylique]]
[[ko:살리실산]]
[[it:Acido salicilico]]
[[he:חומצה סליצילית]]
[[lv:Salicilskābe]]
[[ml:സാലിസിലിക് അമ്ലം]]
[[nl:Salicylzuur]]
[[ja:サリチル酸]]
[[pl:Kwas salicylowy]]
[[pt:Ácido salicílico]]
[[ru:Салициловая кислота]]
[[simple:Salicylic acid]]
[[tr:Salisilik asit]]
[[zh:水楊酸]]


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Latest revision as of 20:28, 4 March 2015

Salicylic acid
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: Ammu Susheela, M.D. [2]

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Overview

Salicylic acid is an anti acne agent that is FDA approved for the treatment of acne, for relief of itching, irritation, redness and scaling assoicated with psoriasis, eczema and seborrheic dermatitis. Common adverse reactions include hypersensitivity reaction, salicylate toxicity.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

  • FOR THE TREATMENT OF ACNE
  • HELPS KEEP SKIN CLEAR OF NEW ACNE BLEMISHES
  • For relief of itching, irritation, redness and scaling assoicated with psoriasis, eczema and seborrheic dermatitis.

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

  • Apply TOPICALLY in concentrations of 0.5% to 10%
  • Disorder of skin, Hyperkeratotic: gel, apply TOPICALLY to the affected area and occlude the area at night.
  • Disorder of skin, Hyperkeratotic
  • shampoo, wet hair and apply TOPICALLY to the scalp, work into a lather and rinse; repeat the treatment as needed until the condition clears [5]
  • Psoriasis
  • Apply TOPICALLY in concentrations of 3% to 6%
  • Removal of wart
  • Apply TOPICALLY once or twice daily in concentrations of 5% to 40% for up to 12 weeks

Non–Guideline-Supported Use

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)

There is limited information regarding FDA-labeled indications and dosage information of Salicylic acid in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Salicylic acid in pediatric patients.

Non–Guideline-Supported Use

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

Contraindications

There is limited information regarding Salicylic acid Contraindications in the drug label.

Warnings

  • For external use only.
  • Avoid contact with eyes. If contact occurs, rinse thoroughly with water.
  • Do not use without consulting a doctor if the condition appears over a large portion of hte body.
  • If condition worsens, or does not improve after using as directed, consult physician.
  • Do not use for prolonged periods without consulting a doctor.

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Salicylic acid in the drug label.

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Salicylic acid in the drug label.

Drug Interactions

There is limited information regarding Salicylic acid Drug Interactions in the drug label.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Salicylic acid in women who are pregnant.

Labor and Delivery

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

Nursing Mothers

There is no FDA guidance on the use of Salicylic acid with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Salicylic acid with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Salicylic acid with respect to geriatric patients.

Gender

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

Race

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

Renal Impairment

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

Hepatic Impairment

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

Females of Reproductive Potential and Males

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

Immunocompromised Patients

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

Administration and Monitoring

Administration

  • Topical

Monitoring

There is limited information regarding Monitoring of Salicylic acid in the drug label.

IV Compatibility

There is limited information regarding IV Compatibility of Salicylic acid in the drug label.

Overdosage

There is limited information regarding Chronic Overdose of Salicylic acid in the drug label.

Pharmacology

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Template:Chembox header2 | Salicylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
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KEGG
UNII
Properties
C7H6O3
Molar mass 138.12 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

  • Salicylic acid has been shown to work through several different pathways. It produces its anti-inflammatory effects via suppressing the activity of cyclooxygenase (COX), an enzyme that is responsible for the production of pro-inflammatory mediators such as the prostaglandins.
  • It does this not by direct inhibition of COX like most other non-steroidal anti-inflammatory drugs (NSAIDs) but instead by suppression of the expression of the enzyme (via a yet-unelucidated mechanism).
  • Salicylic acid has also been shown to activate adenosine monophosphate-activated protein kinase (AMPK), and it is thought that this action may play a role in the anticancer effects of the compound and its prodrugs aspirin and salsalate. In addition, the antidiabetic effects of salicylic acid are likely mediated by AMPK activation primarily through allosteric conformational change that increases levels of phosphorylation.[7]
  • Salicylic acid also uncouples oxidative phosphorylation, which leads to increased ADP:ATP and AMP:ATP ratios in the cell. As a consequence, salicylic acid may alter AMPK activity and subsequently exert its anti-diabetic properties through altered energy status of the cell. Even in AMPK knock-out mice, however, there is an anti-diabetic effect, demonstrating that there is at least one additional, yet-unidentified action of the compound.

[8]

Structure

There is limited information regarding Salicylic acid Structure in the drug label.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Salicylic acid in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Salicylic acid in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Salicylic acid in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Salicylic acid in the drug label.

How Supplied

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

Storage

There is limited information regarding Salicylic acid Storage in the drug label.

Images

Drug Images

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Package and Label Display Panel

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Patient Counseling Information

  • Wash affected areas well with soap and water. Pat dry. Apply cream to affected area one to four times per day, or as directed by physician.

Precautions with Alcohol

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

Brand Names

  • ALA-SEPTIC®[9]

Look-Alike Drug Names

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

Drug Shortage Status

Price

References

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

  1. ↑ 1.0 1.1 1.2 Template:RubberBible92nd
  2. ↑ 2.0 2.1 2.2 2.3 2.4 Template:PubChemLink
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 http://chemister.ru/Database/properties-en.php?dbid=1&id=1777
  4. ↑ 4.0 4.1 4.2 Seidell, Atherton; Linke, William F. (1952). [Google Books Solubilities of Inorganic and Organic Compounds] Check |url= value (help). Van Nostrand. Retrieved 2014-05-29.
  5. ↑ Salicyclic acid. Drugbank.ca. Retrieved on 2012-06-03.
  6. ↑ 6.0 6.1 6.2 Template:Sigma-Aldrich
  7. ↑ Hawley SA, Fullerton MD, Ross FA, Schertzer JD, Chevtzoff C, Walker KJ; et al. (2012). "The ancient drug salicylate directly activates AMP-activated protein kinase". Science. 336 (6083): 918–22. doi:10.1126/science.1215327. PMC 3399766. PMID 22517326 PMID 22517326 Check |pmid= value (help).
  8. ↑ "Newscientist".
  9. ↑ "ALA-SEPTIC- salicylic acid cream".

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