Tiopronin
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| Names | |
|---|---|
| IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid
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| Other names
2-mercaptopropionylglycine
Acadione Thiola |
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| Identifiers | |
1953-02-2  29335-92-0 R |
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| 3D model (Jmol) | Interactive image Interactive image |
| 1859822 | |
| ChEMBL | ChEMBL1314 |
| ChemSpider | 5283 180938 R 643292 S |
| ECHA InfoCard | 100.016.163 |
| EC Number | 217-778-4 |
| KEGG | D01430 |
| MeSH | Tiopronin |
| PubChem | 5483 208825 R 736152 S |
| RTECS number | MC0596500 |
| UNII | C5W04GO61S |
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| 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) | |
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| Legal status |
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| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H302 | |
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EU classification (DSD)
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 Xn |
| R-phrases | R22 |
| S-phrases | S36/37 |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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1,300 mg kg−1 (oral, rat) |
| Related compounds | |
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Related alkanoic acids
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is  ?) |
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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.
Uses[edit]
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[edit]
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]
Costs[edit]
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]
References[edit]
- ^ Lindell, Å.; Denneberg, T.; Hellgren, E.; Jeppsson, J. -O.; Tiselius, H. -G. (1995). "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.
- ^ a b Carlsson, M. S.; Denneberg, T.; Emanuelsson, B.-M.; Kågedal, B.; Lindgren, S. (August 1993). "Pharmacokinetics of oral tiopronin". European Journal of Clinical Pharmacology. 45 (1): 79–84. doi:10.1007/BF00315354. PMID 8405034.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "The huge price hike as sales strategy, taken to extremes by Retrophin". FiercePharma.
- ^ "Why would Martin Shkreli hike an old drug price by 5000%? Only a 'moron' would ask". FierceBiotech.
- ^ "'Pharma bro' Martin Shkreli gouged kids with kidney disease before ripping off AIDS patients". rawstory.com.
- ^ Market Wired Bucillamine article
- ^ "Tiopronin Delayed Release Capsules - $15.35/capsule - ImprimisRx". www.imprimisrx.com. Retrieved 2016-11-01.
