DrugBank: Salicylate-sodium (DB01398)

targets (2)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Not Available

Brand 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

Not Available

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

J T Baker

Dosage forms

Not Available

Prices

Unit description	Cost	Unit
Sodium salicylate crystals	0.09 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

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
logS	-0.52	ALOGPS
pKa (strongest acidic)	2.79	ChemAxon
pKa (strongest basic)	-6.3	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	60.36	ChemAxon
rotatable bond count	1	ChemAxon
refractivity	46.13	ChemAxon
polarizability	12.38	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00566
PharmGKB	PA451428
Wikipedia	http://en.wikipedia.org/wiki/Sodium_salicylate

ATC Codes

D01AE12
S01BC08
N02BA04

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction
Betamethasone	The corticosteroid, betamethasone, may decrease the effect of the salicylate, salicylate-sodium.
Fludrocortisone	The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, salicylate-sodium.
Gliclazide	The salicylate, salicylate-sodium, increases the effect of the sulfonylurea, gliclazide.
Glyburide	The salicylate, salicylate-sodium, increases the effect of the sulfonylurea, glibenclamide.
Hydrocortisone	The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, salicylate-sodium.
Methazolamide	The salicylate, salicylate-sodium, at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Methotrexate	The salicylate, salicylate-sodium, increases the effect and toxicity of methotrexate.
Prednisolone	The corticosteroid, prednisolone, may decrease the effect of the salicylate, salicylate-sodium.
Prednisone	The corticosteroid, prednisone, may decrease the effect of the salicylate, salicylate-sodium.
Probenecid	The salicylate, salicylate-sodium, decreases the uricosuric effect of probenecid.
Sulindac	Risk of additive toxicity (e.g. bleed risk). Salicylate-sodium may decrease the serum concentration of sulindac. Consider alternate therapy or monitor for changes in the therapeutic effects of sulindac and adverse effects of both agents if the interacting agent is initiated, discontinued or dose changed.
Triamcinolone	The corticosteroid, triamcinolone, may decrease the effect of the salicylate, salicylate-sodium.
Warfarin	The antiplatelet effects of sodium salicylate may increase the bleed risk associated with warfarin.

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 Gene: PTGS2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. Pubmed 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 Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed 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 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 Gene: PTGS1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed 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 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 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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:

Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. Pubmed
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
Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed
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
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:

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
Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. Pubmed
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
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
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
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
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 February 08, 2013 16:20