Tiopronin
Thiola · Thiopronin · N-(2-MERCAPTOPROPIONYL)GLYCINE · 2-(2-Mercaptopropanamido)acetic acid · Capen · 2-MPG · Vincol · SF-572
Identifikatoren & physikalische Daten
| CAS No. | 1953-02-2 |
|---|---|
| Summenformel | C5H9NO3S |
| Durchschnittliche Molmasse | 163,2 g/mol |
| Monoisotopische Masse | 163,03031415 g/mol |
| SMILES | CC(S)C(=O)NCC(=O)O |
| InChIKey | YTGJWQPHMWSCST-UHFFFAOYSA-N |
| PubChem CID | 5483 |
| ChEMBL | CHEMBL1314 |
| ChEBI | CHEBI:32229 |
| EC No. | 217-778-4 |
| DTXSID | DTXSID4023678 |
| Lokaler Name | Tiopronin |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 67,4 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 148 |
| Arzneimittel | Pharmaceuticals |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Schmelzpunkt | 93-98 °C |
| Siedepunkt | 418.3±30.0 °C(Predicted) |
| Dichte | 1.249 (estimate) |
| Brechungsindex | 1.5216 (estimate) |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly) |
| pKa (Säurekonstante) | 3.36±0.10(Predicted) |
| Aggregatzustand | solid |
| Farbe | White |
| Merck | 14,9453 |
| BRN | 1859822 |
| Hauptanwendungen | cell analysispeptide synthesis |
| InChI | InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) |
| InChIKey | YTGJWQPHMWSCST-UHFFFAOYSA-N |
| SMILES | C(O)(=O)CNC(=O)C(S)C |
| CAS Datenbank | 1953-02-2(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)TioproninAmbiguous-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2930.90.4950 |
| RTECS-Nr. | MC0596500 |
| R-Sätze (R) | 22 |
| Toxizität | LD50 i.v. in mice: 2.1 g/kg (Fujimura) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
Tiopronin is a sulfiydryl derivative of N-propylglycine useful in the treatment of cystine urolithiasis in children. It is also reportedly effective in the management of rheumatoid polyarthritis, possibly due to its inhibitory effect on the free oxygen radicals produced by inflammatory macrophages and granulocytes.
Verwenden
N-(2-Mercaptopropionyl)glycine or Tiopronin has been used:in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acidsto study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotectionas a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation