Tiopronin

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Tiopronin
Skeletal formula of tiopronin
Names
IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid
Other names
2-mercaptopropionylglycine
Acadione
Thiola
Identifiers
1953-02-2 YesY
29335-92-0 R YesY
1859822
ChEMBL ChEMBL1314 YesY
ChemSpider 5283 YesY
180938 R YesY
643292 S YesY
EC Number 217-778-4
Jmol interactive 3D Image
Image
KEGG D01430 YesY
MeSH Tiopronin
PubChem 5483
208825 R
736152 S
RTECS number MC0596500
UNII C5W04GO61S YesY
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
ATC code R05CB12
QG04BC90
Legal status
  • US: C (Risk not ruled out)
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302
Harmful Xn
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).
YesY verify (what is YesYN ?)
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.[8][9][10] A potential alternative in treatment and costs has arisen with the drug 'Bucillamine'. [11]

References[edit]

  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. ^ a b 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, and 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

External links[edit]