You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameSalicylic acid
Accession NumberDB00936  (APRD01605)
Typesmall molecule
Groupsapproved
Description

A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-CarboxyphenolNot AvailableNot Available
2-Hydroxybenzoic acidNot AvailableNot Available
O-carboxyphenolNot AvailableNot Available
O-hydroxybenzoic acidNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Compound WNot Available
Dr. Scholl's Callus RemoversNot Available
Dr. Scholl's Corn RemoversNot Available
Dr. Scholl's Wart Remover KitNot Available
Duofil Wart RemoverNot Available
DuoplantNot Available
Ionil Plus shampooNot Available
KeralytNot Available
SalonilNot Available
StridexNot Available
Brand mixtures
Brand NameIngredients
MobilatMucopolysaccharide polysulfate + Salicylic acid
Categories
CAS number69-72-7
WeightAverage: 138.1207
Monoisotopic: 138.031694058
Chemical FormulaC7H6O3
InChI KeyYGSDEFSMJLZEOE-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
IUPAC Name
2-hydroxybenzoic acid
SMILES
OC(=O)C1=CC=CC=C1O
Mass Specshow(8.17 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentSalicylic Acids
Alternative parentsBenzoic Acids; Benzoyl Derivatives; Phenols and Derivatives; Enolates; Carboxylic Acids; Enols; Polyamines
Substituentsbenzoyl; phenol derivative; enol; polyamine; carboxylic acid; carboxylic acid derivative; enolate
Classification descriptionThis compound belongs to the salicylic acids. These are ortho-hydroxylated benzoic acids.
Pharmacology
IndicationKey additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts.
PharmacodynamicsSalicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock. Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined the two key ingredients help control diarrhea, nausea, heartburn, and even gas. It is also very mildly anti-biotic.
Mechanism of actionSalicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Salicylic Acid Action PathwayDrug actionSMP00709
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9756
Blood Brain Barrier + 0.6165
Caco-2 permeable + 0.8867
P-glycoprotein substrate Non-substrate 0.734
P-glycoprotein inhibitor I Non-inhibitor 0.9815
P-glycoprotein inhibitor II Non-inhibitor 0.9937
Renal organic cation transporter Non-inhibitor 0.9167
CYP450 2C9 substrate Non-substrate 0.7962
CYP450 2D6 substrate Non-substrate 0.9233
CYP450 3A4 substrate Non-substrate 0.766
CYP450 1A2 substrate Non-inhibitor 0.9517
CYP450 2C9 substrate Non-inhibitor 0.7984
CYP450 2D6 substrate Non-inhibitor 0.9659
CYP450 2C19 substrate Non-inhibitor 0.7644
CYP450 3A4 substrate Non-inhibitor 0.8675
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8525
Ames test Non AMES toxic 0.9829
Carcinogenicity Non-carcinogens 0.8627
Biodegradation Ready biodegradable 0.8086
Rat acute toxicity 2.2160 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9631
hERG inhibition (predictor II) Non-inhibitor 0.9734
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical
DiscTopical
GelTopical
GelTopical
LiquidIntravenous
LiquidOral
LiquidTopical
LotionTopical
OintmentTopical
PatchTopical
PlasterTopical
PowderTopical
PowderTopical
ShampooTopical
SolutionTopical
Solution / dropsOral
SprayTopical
StickTopical
TabletOral
Prices
Unit descriptionCostUnit
Keralyt scalp complete kit67.8USDkit
Keralyt 6% Gel 100 gm Tube51.99USDtube
Keralyt 6% Gel 40 gm Tube49.99USDtube
Compound W 17% Liquid 9.3ml Bottle11.99USDbottle
Keralyt 3% Gel 28.4 gm Tube11.35USDtube
Sastid soap4.32USDeach
Salicylic acid 6% gel1.14USDg
Salactic film solution0.74USDml
Compound w pads0.5USDeach
Keralyt 6% gel0.5USDg
Freezone corn-callus liquid0.42USDml
Keralyt 3% gel0.39USDg
Salicylic acid 6% shampoo0.21USDml
Ionil plus 2% shampoo0.05USDml
Ionil t plus shampoo0.05USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point158 °CPhysProp
boiling point211 °C at 2.00E+01 mm HgPhysProp
water solubility2240 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.26HANSCH,C ET AL. (1995)
logS-1.82ADME Research, USCD
Caco2 permeability-4.79ADME Research, USCD
pKa2.97SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
water solubility1.13e+01 g/lALOGPS
logP1.96ALOGPS
logP1.98ChemAxon
logS-1.1ALOGPS
pKa (strongest acidic)2.79ChemAxon
pKa (strongest basic)-6.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area57.53ChemAxon
rotatable bond count1ChemAxon
refractivity35.3ChemAxon
polarizability12.81ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Howard Jones, Robert W. Houser, “Process for preparing 4-(2,4-difluorophenyl)-salicyclic acid.” U.S. Patent US4225730, issued August, 1972.

US4225730
General Reference
  1. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed
  2. Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. Pubmed
External Links
ResourceLink
KEGG DrugD00097
KEGG CompoundC00805
PubChem Compound338
PubChem Substance46504942
ChemSpider331
BindingDB26193
ChEBI16914
ChEMBL
Therapeutic Targets DatabaseDAP000731
PharmGKBPA451299
IUPHAR4306
Guide to Pharmacology4306
HETSAL
Drug Product Database2241935
WikipediaSalicyclic_acid
ATC CodesD11AC30N02BA04
AHFS Codes
  • 24:16.00
  • 28:08.04.24
  • 84:28.00
  • 92:02.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Moon C, Ahn M, Jee Y, Heo S, Kim S, Kim H, Sim KB, Koh CS, Shin YG, Shin T: Sodium salicylate-induced amelioration of experimental autoimmune encephalomyelitis in Lewis rats is associated with the suppression of inducible nitric oxide synthase and cyclooxygenases. Neurosci Lett. 2004 Feb 12;356(2):123-6. Pubmed
  2. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed
  3. Sun R, Carlson NG, Hemmert AC, Kishore BK: P2Y2 receptor-mediated release of prostaglandin E2 by IMCD is altered in hydrated and dehydrated rats: relevance to AVP-independent regulation of IMCD function. Am J Physiol Renal Physiol. 2005 Sep;289(3):F585-92. Epub 2005 Apr 19. Pubmed
  4. Celik G, Pasaoglu G, Bavbek S, Abadoglu O, Dursun B, Mungan D, Misirligil Z: Tolerability of selective cyclooxygenase inhibitor, celecoxib, in patients with analgesic intolerance. J Asthma. 2005 Mar;42(2):127-31. Pubmed
  5. Liu X, Lee TL, Wong PT: Cyclooxygenase-1 inhibition shortens the duration of diazepam-induced loss of righting reflex in mice. Anesth Analg. 2006 Jan;102(1):135-40. Pubmed
  6. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed
  2. Fiebich BL, Chrubasik S: Effects of an ethanolic salix extract on the release of selected inflammatory mediators in vitro. Phytomedicine. 2004 Feb;11(2-3):135-8. Pubmed
  3. Chae HJ, Chae SW, Reed JC, Kim HR: Salicylate regulates COX-2 expression through ERK and subsequent NF-kappaB activation in osteoblasts. Immunopharmacol Immunotoxicol. 2004 Feb;26(1):75-91. Pubmed
  4. Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. Pubmed
  5. Elvira C, Gallardo A, Lacroix N, Schacht E, San Roman J: Incorporation of salicylic acid derivatives to hydrophilic copolymer systems with biomedical applications. J Mater Sci Mater Med. 2001 Jun;12(6):535-42. Pubmed
  6. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed

3. Aldo-keto reductase family 1 member C1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Aldo-keto reductase family 1 member C1 Q04828 Details

References:

  1. Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed
  2. Xiao HR, Sheng LQ, Shi CH, Xu XL, Xie YS, Liu QL: [Fluorescence study on the interaction of salicylic acid and bovine serum albumin] Guang Pu Xue Yu Guang Pu Fen Xi. 2004 Jan;24(1):78-81. Pubmed
  3. Yin T, Wei W, Yang L, Liu K, Gao X: Kinetics parameter estimation for the binding process of salicylic acid to human serum albumin (HSA) with capacitive sensing technique. J Biochem Biophys Methods. 2007 Jun 10;70(4):587-93. Epub 2007 Jan 27. Pubmed
  4. Yu T, Tao Z: [Fluorescence study on the interaction of salicylic acid and human serum albumin] Guang Pu Xue Yu Guang Pu Fen Xi. 1999 Jun;19(3):453-5. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. Pubmed
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed
  3. Race JE, Grassl SM, Williams WJ, Holtzman EJ: Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun. 1999 Feb 16;255(2):508-14. Pubmed
  4. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. Pubmed
  5. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. Pubmed

2. Solute carrier family 22 member 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 10 Q63ZE4 Details

References:

  1. Youngblood GL, Sweet DH: Identification and functional assessment of the novel murine organic anion transporter Oat5 (Slc22a19) expressed in kidney. Am J Physiol Renal Physiol. 2004 Aug;287(2):F236-44. Epub 2004 Apr 6. Pubmed

3. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. Pubmed
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed
  3. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. Pubmed

4. Solute carrier family 22 member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

References:

  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. Pubmed

5. Solute carrier organic anion transporter family member 2B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

References:

  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. Pubmed

6. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. Pubmed

7. Monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

References:

  1. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. Pubmed

8. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed
  2. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. Pubmed
  3. Morita N, Kusuhara H, Sekine T, Endou H, Sugiyama Y: Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1179-84. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 26, 2014 15:26