2-(2-hydroxybenzoyloxy)benzoic acid

• ChemBase ID: 1210
• Molecular Formular: C14H10O5
• Molecular Mass: 258.2262
• Monoisotopic Mass: 258.05282342
• SMILES: O(c1c(cccc1)C(=O)O)C(=O)c1c(O)cccc1
• Canonical SMILES: Oc1ccccc1C(=O)Oc1ccccc1C(=O)O
• InChI: InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)
• InChIKey: WVYADZUPLLSGPU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-hydroxybenzoyloxy)benzoic acid
• IUPAC Traditional name: salina; 2-(2-hydroxybenzoyloxy)benzoic acid
• Brand Name: Disalcid
• Synonyms: Sasapyrine; 2-(2-Hydroxybenzoyl)oxybenzoic acid; 2-Hydroxybenzoic acid 2-carboxyphenyl ester; disalicylic acid; salicyloxysalicylic acid; Salsalate; Sasapyrine; Salsalatum [inn-latin]; salicylsalicylic acid; Salsalate; Salicylic Acid Salicylate; Diacesal; Diplosal; Disalcid; Disalgesic; Disalyl; Mono-Gesic; NSC 49171; Nobacid; Salflex; Salical; Salicyl Salicylate; Salicyloylsalicylic Acid; Salina; Salsalate; Salysal; Sasapirin; Sasapyrinum; o-Salicylsalicylic Acid; Salicylsalicylic acid; 2-((2-Hydroxybenzoyl)oxy)benzoic acid; 水杨基水杨酸

Database IDs

• CAS Number: 552-94-3
• EC Number: 209-027-4
• MDL Number: MFCD00020252
• PubChem SID: 160964671; 46506882
• PubChem CID: 5161

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4033105
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5542619
• LogD (pH = 7.4): 0.23430523
• Log P: 3.6386988
• Molar Refractivity: 67.098 cm^3
• Polarizability: 25.454422 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -3.02
• Solubility (Water): 2.46e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: white to tan powder
• Melting Point: 132-138°C

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: DH2080000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50; 36/37/38
• Safety Statements: 26-37; 61
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P273
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (HPLC); 95+%; 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C14H10O5

DETAILS

DrugBank - DB01399

• Drug Groups: approved
• Description: Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo. Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body. The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.
• Indication: For relief of the signs and symptoms of rheumatoid arthritis, osteoarthritis and related rheumatic disorders.
• Pharmacology: Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo.
• Toxicity: Death has followed ingestion of 10 to 30 g of salicylates in adults, but much larger amounts have been ingested without fatal outcome.
• Affected Organisms: Humans and other mammals
• Biotransformation: Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body.
• Absorption: Salsalate is insoluble in acid gastric fluids (< 0.1 mg/ml at pH 1.0), but readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged. The amount of salicylic acid available from salsalate is about 15% less than from aspirin, when the two drugs are administered on a salicylic acid molar equivalent basis (3.6 g salsalate/5 g aspirin). Food slows the absorption of all salicylates including salsalate.
• Half Life: The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.
• Protein Binding: Salicylate: 90-95% bound at plasma salicylate concentrations <100 mcg/mL; 70-85% bound at concentrations of 100-400 mcg/mL; 25-60% bound at concentrations >400 mcg/mL.
• External Links: RxList; PDRhealth; Drugs.com

Sigma Aldrich - SML0070

Biochem/physiol Actions
Salsalate is a nonsteroidal anti-inflammatory drug (NSAID), a nonacetylated salicylate with no more problems of gastrointestinal bleeding than placebo. It inhibits synthesis and release of prostaglandins through the inactivation of cyclooxygenase-1 (COX-1) and COX-2. Salsalate is currently being investigated as a treatment for Type 2 diabetes with possible use to prevent the disease in people at risk. It reduces blood glucose concentrations in patients with type 2 diabetes, as well as in insulin-resistant patients without diabetes.

Toronto Research Chemicals - S095700

Nonacetylated aspirin analog. Analgesic, anti-inflammatory.

REFERENCES

• Harrison, L.L., et al.: J. Pharm. Sci., 69, 1268 (1980)
• Dromgoole, S.M., et al.: J. Pharm. Sci., 73, 1657 (1980)