|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|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)|
|G04BX16 (WHO) QG04BX16 (WHO)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|1,300 mg kg−1 (oral, rat)|
Related alkanoic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
what is ?)(
|CompTox Dashboard (EPA)|
Tiopronin, sold under the brand name Thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria. Due to the rarity of the disorder, tiopronin falls under the classification of an orphan drug. It is somewhat similar to penicillamine in both chemistry and pharmacology.
A generic version of tiopronin is available in the United States as of April 2021.
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. The drug works by reacting with urinary cysteine to form a more soluble, disulfide linked, tiopronin-cysteine complex.
Tiopronin may present a variety of side effects, which are broadly similar to those of D-penicillamine and other compounds containing active sulfhydryl groups. Its pharmacokinetics have been studied.
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.
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, though tiopronin is not an anti-inflammatory.
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- "Tiopronin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 18 June 2021.
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- Delecoeuillerie G (April 1989). "[Tolerability and therapeutic maintenance of tiopronin, new basic treatment of rheumatoid arthritis. Apropos of long-term follow-up of 268 cases]". Revue du Rhumatisme et des Maladies Osteo-Articulaires. 56 (5 Pt 2): 38–42. PMID 2740804.
- Pasero G, Pellegrini P, Ambanelli U, Ciompi ML, Colamussi V, Ferraccioli G, et al. (August 1982). "Controlled multicenter trial of tiopronin and d-penicillamine for rheumatoid arthritis". Arthritis and Rheumatism. 25 (8): 923–9. doi:10.1002/art.1780250803. PMID 7115451.
- Dahl JA, Maddux BL, Hutchison JE (June 2007). "Toward greener nanosynthesis". Chemical Reviews. 107 (6): 2228–69. CiteSeerX 10.1.1.454.2724. doi:10.1021/cr050943k. PMID 17564480.
- "Tiopronin". Drug Information Portal. U.S. National Library of Medicine.