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targets (2)
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Identification
Name Salicylate-sodium
Accession Number DB01398
Type small molecule
Groups approved
Description

Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure.

It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID) and induces apoptosis in cancer cells. It is also potential replacement for aspirin for people sensitive to it.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names Not Available
Brand name mixtures Not Available
Categories
  • Nonsteroidal Anti-inflammatory Agents (NSAIAs)
  • Salicylates
CAS number Not Available
Weight Average: 160.1026
Monoisotopic: 160.013638701
Chemical Formula C7H5NaO3
InChI Key InChIKey=ABBQHOQBGMUPJH-UHFFFAOYSA-M
InChI
InChI=1S/C7H6O3.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1
Plain Text
IUPAC Name
sodium 2-hydroxybenzoate
SMILES
[Na+].OC1=CC=CC=C1C([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID)
Pharmacodynamics Non-steroidal anti-inflammatory drugs such as Salicylate-sodium work by inhibiting the enzyme cyclooxygenase (COX), which converts arachidonic acid to prostaglandin H2 (PGH2). PGH2, in turn, is converted by other enzymes to several other prostaglandins (which are mediators of pain, inflammation, and fever)
Mechanism of action Salicylate-sodium is considered a non-selective COX inhibitor—that is, it inhibits two isoforms of cyclooxygenase, COX-1 and COX-2. The analgesic, antipyretic, and anti-inflammatory activity of NSAIDs appears to be achieved mainly through inhibition of COX-2, whereas inhibition of COX-1 would be responsible for unwanted effects on platelet aggregation and the gastrointestinal tract. However, the role of the individual COX isoforms in the analgesic, anti-inflammatory, and gastric damage effects of NSAIDs is uncertain and different compounds cause different degrees of analgesia and gastric damage. Salicylate-sodium 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Sodium salicylate crystals 0.09 USD g
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 4.81e+01 g/l ALOGPS
logP 1.36 ALOGPS
logP 1.98 ChemAxon Molconvert
logS -0.52 ALOGPS
pKa 13.23 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 60.36 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 46.13 ChemAxon Molconvert
polarizability 12.38 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00566 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Sodium_salicylate Link_out
ATC Codes
  • D01AE12
  • S01BC08
  • N02BA04
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. Pubmed
  2. Zheng L, Howell SJ, Hatala DA, Huang K, Kern TS: Salicylate-based anti-inflammatory drugs inhibit the early lesion of diabetic retinopathy. Diabetes. 2007 Feb;56(2):337-45. Pubmed
  3. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed
  4. 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
  5. 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

2. Prostaglandin G/H synthase 1

Pharmacological action: yes
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on July 08, 2007 11:05 / Updated on January 09, 2011 08:48

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.