Salsalat
SALSALATE · 2-[(2-Hydroxybenzoyl)oxy]benzoic acid · Arcylate · Aspirin IMpurity E · Salina · diagen · Salysal · Disalyl
Identifikatoren & physikalische Daten
| CAS No. | 552-94-3 |
|---|---|
| Summenformel | C14H10O5 |
| Durchschnittliche Molmasse | 258,23 g/mol |
| Monoisotopische Masse | 258,05282342 g/mol |
| SMILES | O=C(Oc1ccccc1C(=O)O)c1ccccc1O |
| InChIKey | WVYADZUPLLSGPU-UHFFFAOYSA-N |
| PubChem CID | 5161 |
| ChEMBL | CHEMBL154111 |
| ChEBI | CHEBI:9014 |
| EC No. | 209-027-4 |
| DTXSID | DTXSID1023572 |
| Lokaler Name | Salsalat |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 341 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Löslichkeit | 2.46e-01 g/LDMSO: ≥15mg/mLHYDROLYSIS |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, Nonsteroidal |
| Schmelzpunkt | 147 °C139-151 °C |
| Physical Description | Solid |
| Collision Cross Section | 151.3 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]153.86 Ų [M+H]+ [CCS Type: TW |
| Siedepunkt | 361.48°C (rough estimate) |
| Dichte | 1.3326 (rough estimate) |
| Brechungsindex | 1.4825 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pKa 3.5 (Uncertain)9.8 (Uncertain) |
| Farbe | white to tan |
| Merck | 14,8339 |
| 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 |
| SMILES | OC(=O)c1ccccc1OC(=O)c2ccccc2O |
| CAS Datenbank | 552-94-3 |
| NIST chemische Informationen | 2-Carboxyphenyl salicylate(552-94-3) |
| EPA chemische Informationen | Benzoic acid, 2-hydroxy-, 2-carboxyphenyl ester (552-94-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (87.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (87.2%) |
| Hepatotoxicity | Prospective studies show that a proportion of patients taking salsalate experience at least transient serum aminotransferase elevations particularly when it is given in higher doses. These abnormalities may resolve even with drug continuation or after dose reduction. Marked aminotransferase elevations (>10 fold elevated) occur rarely except with use of higher doses (4 g daily or more) in a manner similar to aspirin. Clinically apparent liver injury with jaundice from salsalate has not been reported and must be very rare. Salsalate is probably capable of inducing Reye syndrome in a susceptible child or adolescent and, like aspirin, should be avoided in those age groups. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)SalsalatevLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9 / PGIII |
| Zollcode | 29182300 |
| RTECS-Nr. | DH2080000 |
| R-Sätze (R) | 36/37/38-50-22 |
| Gefahrensymbole | Xi,N,Xn |
Anwendungen & Verwendung
Beschreibung
Salsalate, or salicylsalicylic acid, (pKa 3.5 [COOH], 9.8 [AR-OH]) is a dimer of salicylic acid. It is insoluble in gastric juice but is soluble in the small intestine, where it is partially hydrolyzed to two molecules of salicylic acid and absorbed. On a molar basis, it produces 15% less salicylic acid than aspirin. It does not cause GI blood loss and can be given to aspirin-sensitive patients. Salsalate is available as capsules and tablets.
Verwenden
Nonacetylated (e.g., sodium salicylate) and acetylated (aspirin) forms of salicylate are widely used to target inflammation in the treatment of insulin resistance, type 2 diabetes, or rheumatic pain. Sasapyrine is a dimeric prodrug comprising two esterified salicylate moieties. It is advantageous over sodium salicylate because it is insoluble at the acid pH of the stomach and passes suspended but undissolved into the small intestine, sparing the gastric mucosa direct contact.