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Tiopronin

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Tiopronin
Skeletal formula of tiopronin
Names
IUPAC name acetic acid
Other names Thiopronine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1859822
ChEMBL
ChemSpider
ECHA InfoCard 100.016.163 Edit this at Wikidata
EC Number
  • 217-778-4
KEGG
MeSH Tiopronin
PubChem CID
RTECS number
  • MC0596500
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)Key: YTGJWQPHMWSCST-UHFFFAOYSA-N
SMILES
  • CC(S)C(=O)NCC(O)=O
Properties
Chemical formula C5H9NO2S
Molar mass 147.19 g·mol
Appearance White, opaque crystals
log P −0.674
Acidity (pKa) 3.356
Basicity (pKb) 10.641
Pharmacology
Legal status
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1.300 mg kg (oral, rat)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tiopronin (trade name Thiola) is a prescription thiol drug used to control the rate of cystine precipitation and excretion in the disease cystinuria. Due to the rarity of the disorder, tioronin falls under the classification of an orphan drug.

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.

It may also be used for Wilson's disease (an overload of copper in the body), and certain types of rare arthritis. It should be mentioned though, that 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.

Side effects

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

  1. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

Cough and cold preparations (R05)
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
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