Tiopronin
 | |
| Names | |
|---|---|
| IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid | |
| Other names
2-mercaptopropionylglycine | |
| Identifiers | |
| ATC code | R05 QG04BC90 |
| 1859822 | |
1953-02-2  29335-92-0 R | |
| ChEMBL | ChEMBL1314 |
| ChemSpider | 5283 180938 R 643292 S |
| EC number | 217-778-4 |
| |
| Jmol-3D images | Image Image |
| KEGG | D01430 |
| MeSH | Tiopronin |
| PubChem | 5483 208825 R 736152 S |
| RTECS number | MC0596500 |
| |
| UNII | C5W04GO61S |
| Properties | |
| Molecular formula |
C5H9NO3S |
| Molar mass | 163.19 g·mol−1 |
| Appearance | White, opaque crystals |
| Melting point | 93 °C (199 °F; 366 K) |
| log P | −0.674 |
| Acidity (pKa) | 3.356 |
| Basicity (pKb) | 10.641 |
| Pharmacology | |
| Legal status |
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| |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H302 | |
| EU classification |  Xn |
| R-phrases | R22 |
| S-phrases | S36/37 |
| LD50 (Median lethal dose) |
1,300 mg kg−1 (oral, rat) |
| Related compounds | |
| Related alkanoic acids |
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| Related compounds |
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| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
verify (what is: / ?) | |
| Infobox references | |
Tiopronin (trade name Thiola) is a prescription thiol drug used to control the rate of cystine precipitation and excretion in the disease cystinuria.[1][2] Due to the rarity of the disorder, tiopronin falls under the classification of an orphan drug.
Uses
Tiopronin is used primarily for cystinuria and is well known in the cystinuric community. Depending on the severity of a person's cystinuria, tiopronin may be taken for life, possibly starting in early childhood.
It may also be used for Wilson's disease (an overload of copper in the body), and certain rare types of arthritis, though tiopronin is not an anti-inflammatory.
Tiopronin is also sometimes used as a stabilizing agent for metal nanoparticles. The thiol group binds to the nanoparticles, preventing coagulation.[3]
Side effects
Tiopronin may present a wide variety of side effects, but side effects are usually limited and subside over time with continued usage. Due to the rarity of the disease cystinuria, tiopronin has not been studied substantially.
References
- ↑ Lindell, Å.; Denneberg, T.; Hellgren, E.; Jeppsson, J. -O.; Tiselius, H. -G. "Clinical course and cystine stone formation during tiopronin treatment". Urological Research 23 (2): 111–117. doi:10.1007/BF00307941.
- ↑ Coe, Fredric L.; Parks, Joan H.; Asplin, John R. (15 October 1992). "The Pathogenesis and Treatment of Kidney Stones". New England Journal of Medicine 327 (16): 1141–1152. doi:10.1056/NEJM199210153271607.
- ↑ Jennifer A. Dahl, Bettye L. S. Maddux, and James E. Hutchison (2007). "Toward Greener Nanosynthesis". Chemical Reviews 107 (6): 2228–2269. doi:10.1021/cr050943k. PMID 17564480.
External links
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