Tiopronin

Tiopronin
Identifiers
CAS number	1953-02-2 Y, 29335-92-0 R Y
PubChem	5483, 208825 R, 736152 S
ChemSpider	5283 Y, 180938 R Y, 643292 S Y
UNII	C5W04GO61S Y
EC number	217-778-4
KEGG	D01430 Y
MeSH	Tiopronin
ChEMBL	CHEMBL1314 Y
RTECS number	MC0596500
ATC code	R05CB12,QG04BC90
Beilstein Reference	1859822
Jmol-3D images	{{#if:CC(S)c(:[o]):[nH]Cc(:[o]):[oH]CC(S)C(=O)NCC(O)=O|Image 1 Image 2
SMILES CC(S)c(:[o]):[nH]Cc(:[o]):[oH] CC(S)C(=O)NCC(O)=O
InChI InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) Y Key: YTGJWQPHMWSCST-UHFFFAOYSA-N Y
Properties
Molecular formula	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
Legal status	℞-only(US)
Pregnancy category	C(US)
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
EU classification	Xn
R-phrases	R22
S-phrases	S36/37
LD50	1,300 mg kg−1 (oral, rat)
Related compounds
Related alkanoic acids	Acetylcysteine Glycylglycine Iminodiacetic acid Nitrilotriacetic acid N-Oxalylglycine Bucillamine Oxalyldiaminopropionic acid gamma-Glutamylcysteine
Related compounds	N-Acetylglycinamide
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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. 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, 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.^[1]

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

External links

• Thiola Main Site