Tiopronin

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Tiopronin
Skeletal formula of tiopronin
Names
IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid
Other names
2-mercaptopropionylglycine
Identifiers
ATC code R05CB12
QG04BC90
1859822
1953-02-2 YesY
29335-92-0 R YesY
ChEMBL ChEMBL1314 YesY
ChemSpider 5283 YesY
180938 R YesY
643292 S YesY
EC number 217-778-4
Jmol-3D images 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 °C (199 °F; 366 K)
log P −0.674
Acidity (pKa) 3.356
Basicity (pKb) 10.641
Pharmacology
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
EU classification Harmful Xn
R-phrases R22
S-phrases S36/37
1,300 mg kg−1 (oral, rat)
Related compounds
Related alkanoic acids
Related compounds
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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.

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.

It may also be used for Wilson's disease (an overload of copper in the body), and certain rare types of arthritis, 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.[3]

Side effects[edit]

Tiopronin may present a wide variety of side effects, but side effects are usually limited and subside over time with continued usage. Due to the rarity of the disease cystinuria, tiopronin has not been studied substantially.

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. ^ 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. 

External links[edit]