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 3D model Interactive image
Interactive image
KEGG D01430 YesY
MeSH Tiopronin
PubChem 5483
208825 R
736152 S
RTECS number MC0596500
UNII C5W04GO61S YesY
  • InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) YesY
    Key: YTGJWQPHMWSCST-UHFFFAOYSA-N YesY
  • CC(S)c(:[o]):[nH]Cc(:[o]):[oH]
  • CC(S)C(=O)NCC(O)=O
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 (WHO)
Legal status
  • US: C (Risk not ruled out)
Vapor pressure {{{value}}}
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

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]

Costs

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

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External links

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  11. ↑ Market Wired Bucillamine article
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