tiopronin tiopronin tiopronin, sold under the brand name thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria. tiopronin names iupac name n-(2-sulfanylpropanoyl)glycine systematic iupac name (2-sulfanylpropanamido)acetic acid other names 2-mercaptopropionylglycineacadione identifiers cas number 1953-02-2 y29335-92-0 r y 3d model (jsmol) interactive image beilstein reference 1859822 chembl chembl1314 y chemspider 5283 y180938 r y643292 s y echa infocard 100.016.163 ec number 217-778-4 kegg d01430 y mesh tiopronin pubchem cid 5483208825 r736152 s rtecs number mc0596500 unii c5w04go61s yx294k8k2pf r y comptox dashboard (epa) dtxsid4023678 inchi inchi=1s/c5h9no3s/c1-3(10)5(9)6-2-4(7)8/h3,10h,2h2,1h3,(h,6,9)(h,7,8) ykey: ytgjwqphmwscst-uhfffaoysa-n y smiles cc(s)c(=o)ncc(o)=o properties chemical 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 atc code g04bx16 (who) qg04bx16 (who) routes ofadministration by mouth legal status us: ℞-only hazards ghs labelling: pictograms signal word warning hazard statements h302 lethal dose or concentration (ld, lc): ld50 (median dose) 1,300 mg kg−1 (oral, rat) related compounds related alkanoic acids acetylcysteineglycylglycineiminodiacetic acidnitrilotriacetic acidn-oxalylglycinebucillamineoxalyldiaminopropionic acidgamma-glutamylcysteine related compounds n-acetylglycinamide except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references tioproninclinical datatrade namesthiolalicense data us dailymed: tiopronin identifiersdrugbankdb06823chebichebi:32229comptox dashboard (epa)dtxsid4023678 echa infocard100.016.163 a generic version of tiopronin is available in the united states as of april 2021. a generic version of the delayed-release version is also available. medical uses tiopronin is indicated, in combination with high fluid intake, alkali, and diet modification, for the prevention of cystine stone formation in people 20 kilograms (44 lb) and greater with severe homozygous cystinuria, who are not responsive to these measures alone. 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. its pharmacokinetics have been studied. pharmacology mechanism of action tiopronin works by reacting with urinary cysteine to form a more soluble, disulfide linked, tiopronin-cysteine complex. society and culture in the u.s., the drug was marketed by mission pharmacal at $1.50 per pill, but in 2014 the rights were bought by retrophin, owned by martin shkreli, and the price increased to $30 per pill for a 100 mg capsule. in 2016 imprimis pharmaceuticals introduced a lower cost version marketed as a compounded drug. research 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, 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.