Tiopronin
Chemical compound
From Wikipedia, the free encyclopedia
Tiopronin, sold under the brand name Thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria.[3][4]
| |
| Names | |
|---|---|
| IUPAC name
N-(2-Sulfanylpropanoyl)glycine | |
| Systematic IUPAC name
(2-Sulfanylpropanamido)acetic acid | |
| Other names
2-mercaptopropionylglycine Acadione | |
| Identifiers | |
3D model (JSmol) |
|
| 1859822 | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.016.163 |
| EC Number |
|
| KEGG | |
| MeSH | Tiopronin |
PubChem CID |
|
| RTECS number |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C5H9NO3S | |
| Molar mass | 163.19 g·mol−1 |
| Appearance | White, opaque crystals |
| Melting point | 93 to 98 °C (199 to 208 °F; 366 to 371 K) |
| log P | −0.674 |
| Acidity (pKa) | 3.356 |
| Basicity (pKb) | 10.641 |
| Pharmacology | |
| G04BX16 (WHO) QG04BX16 (WHO) | |
| By mouth | |
| Legal status | |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H302 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
1,300 mg kg−1 (oral, rat) |
| Related compounds | |
Related alkanoic acids |
|
Related compounds |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
| Clinical data | |
|---|---|
| Trade names | Thiola |
| License data | |
| Identifiers | |
| DrugBank | |
| ChEBI | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.016.163 |
It is available as a generic medication.[5][6]
Medical uses
Side effects
Tiopronin may present a variety of side effects, which are broadly similar to those of D-penicillamine and other compounds containing active sulfhydryl groups.[7] Its pharmacokinetics have been studied.[8]
Pharmacology
Society and culture
In the U.S., the drug was marketed by Mission Pharmacal at $1.50 per pill, but in 2014 the rights were bought by Retrophin, owned by Martin Shkreli, and the price increased to $30 per pill for a 100 mg capsule.[9][10]
In 2016 Imprimis Pharmaceuticals introduced a lower cost version marketed as a compounded drug.[11]
Research
It may also be used for Wilson's disease (an overload of copper in the body), and has also been investigated for the treatment of arthritis,[12][13] though tiopronin is not an anti-inflammatory.[citation needed]
Tiopronin is also sometimes used as a stabilizing agent for metal nanoparticles. The thiol group binds to the nanoparticles, preventing coagulation.[14]
