IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid
Other names
1953-02-2 YesY
29335-92-0 R YesY
3D model (Jmol) Interactive image
Interactive image
ChemSpider 5283 YesY
180938 R YesY
643292 S YesY
ECHA InfoCard 100.016.163
EC Number 217-778-4
KEGG D01430 YesY
MeSH Tiopronin
PubChem 5483
208825 R
736152 S
RTECS number MC0596500
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
R05CB12 (WHO) QG04BC90 (WHO)
  • US: C (Risk not ruled out)
Legal status
GHS pictograms
GHS signal word WARNING
R-phrases R22
S-phrases S36/37
Lethal dose or concentration (LD, LC):
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).
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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. It is somewhat similar to penicillamine in both chemistry and pharmacology.


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.[3]

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,[4][5] 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.[6]

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 pharmokinetics have been studied.[3]


In the U.S., the drug was marketed by Mission Pharmacal at $1.50 per pill, but the rights were bought by Retrophin, owned by Martin Shkreli, and the price increased to $30 per pill for a 100mg capsule.[8][9][10] A potential alternative in treatment and costs has arisen with the drug 'Bucillamine'.[11] There is now a low-cost alternative available from Imprimis Pharmaceuticals Inc., Tiopronin Delayed Release, at $7.68 for 100mg.[12]


  1. 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.
  2. 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.
  3. 1 2 Carlsson, M. S.; Denneberg, T.; Emanuelsson, B.-M.; K�gedal, B.; Lindgren, S. (August 1993). "Pharmacokinetics of oral tiopronin". European Journal of Clinical Pharmacology. 45 (1): 79–84. doi:10.1007/BF00315354. replacement character in |last4= at position 2 (help)
  4. Delecoeuillerie, G (30 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.
  5. Pasero, Giampiero; Pellegrini, Pietro; Ambanelli, Umberto; Ciompi, Maria Laura; Colamussi, Vincenzo; Ferraccioli, Gianfranco; Barbieri, Paola; Mazzoni, Maria Rosa; Menegale, Germano; Trippi, Donatella (August 1982). "Controlled multicenter trial of tiopronin and D-penicillamine for rheumatoid arthritis". Arthritis & Rheumatism. 25 (8): 923–929. doi:10.1002/art.1780250803.
  6. Jennifer A. Dahl; Bettye L. S. Maddux & James E. Hutchison (2007). "Toward Greener Nanosynthesis". Chemical Reviews. 107 (6): 2228–2269. doi:10.1021/cr050943k. PMID 17564480.
  7. Jaffe, Israeli A. (March 1986). "Adverse effects profile of sulfhydryl compounds in man". The American Journal of Medicine. 80 (3): 471–476. doi:10.1016/0002-9343(86)90722-9.
  8. "The huge price hike as sales strategy, taken to extremes by Retrophin". FiercePharma.
  9. "Why would Martin Shkreli hike an old drug price by 5000%? Only a 'moron' would ask". FierceBiotech.
  10. "'Pharma bro' Martin Shkreli gouged kids with kidney disease before ripping off AIDS patients". rawstory.com.
  11. Market Wired Bucillamine article
  12. "Tiopronin Delayed Release Capsules - $15.35/capsule - ImprimisRx". www.imprimisrx.com. Retrieved 2016-11-01.
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