| 词条 | Tiopronin |
| 释义 |
| Watchedfields = changed | verifiedrevid = 470610633 | ImageFile = Tiopronin.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageName = Skeletal formula of tiopronin | IUPACName = 2-(2-sulfanylpropanoylamino)acetic acid | OtherNames = 2-mercaptopropionylglycine Acadione Thiola |Section1={{Chembox Identifiers | CASNo = 1953-02-2 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo1 = 29335-92-0 | CASNo1_Ref = {{cascite|correct|??}} | CASNo1_Comment = R | PubChem = 5483 | PubChem1 = 208825 | PubChem1_Comment = R | PubChem2 = 736152 | PubChem2_Comment = S | ChemSpiderID = 5283 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 180938 | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Comment = R | ChemSpiderID2 = 643292 | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2_Comment = S | UNII = C5W04GO61S | UNII_Ref = {{fdacite|correct|FDA}} | EINECS = 217-778-4 | KEGG = D01430 | KEGG_Ref = {{keggcite|correct|kegg}} | MeSHName = Tiopronin | ChEMBL = 1314 | ChEMBL_Ref = {{ebicite|correct|EBI}} | RTECS = MC0596500 | Beilstein = 1859822 | SMILES = CC(S)C(=O)NCC(=O)O | StdInChI = 1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YTGJWQPHMWSCST-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=5 | H=9 | N=1 | S=1 | O=3 | Appearance = White, opaque crystals | MeltingPtC = 93 to 98 | LogP = −0.674 | pKa = 3.356 | pKb = 10.641 }} |Section6={{Chembox Pharmacology | ATCCode_prefix = G04 | ATCCode_suffix = BX16 | ATC_Supplemental = | Legal_US = Rx | Pregnancy_US = C }} |Section7={{Chembox Hazards | GHSPictograms = {{gHS exclamation mark}} | GHSSignalWord = WARNING | HPhrases = {{h-phrases|302}} | LD50 = 1,300 mg kg−1 (oral, rat) }} |Section8={{Chembox Related | OtherFunction_label = alkanoic acids | OtherFunction = {{unbulleted list|Acetylcysteine|Glycylglycine|Iminodiacetic acid|Nitrilotriacetic acid|N-Oxalylglycine|Bucillamine|Oxalyldiaminopropionic acid|gamma-Glutamylcysteine}} | OtherCompounds = {{unbulleted list|N-Acetylglycinamide}} }} }} 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. UsesTiopronin 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 effectsTiopronin 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 pharmacokinetics have been studied.[3] Society and cultureIn 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 100mg capsule.[8][9] In 2016 Imprimis Pharmaceuticals introduced a lower cost version marketed as a compounded drug.[10] References1. ^{{cite journal|last1=Lindell|first1=Å.|last2=Denneberg|first2=T.|last3=Hellgren|first3=E.|last4=Jeppsson|first4=J. -O.|last5=Tiselius|first5=H. -G.|title=Clinical course and cystine stone formation during tiopronin treatment|journal=Urological Research|volume=23|issue=2|pages=111–117|doi=10.1007/BF00307941|year=1995}} 2. ^{{cite journal|last1=Coe|first1=Fredric L.|last2=Parks|first2=Joan H.|last3=Asplin|first3=John R.|title=The Pathogenesis and Treatment of Kidney Stones|journal=New England Journal of Medicine|date=15 October 1992|volume=327|issue=16|pages=1141–1152|doi=10.1056/NEJM199210153271607}} 3. ^1 {{cite journal|last1=Carlsson|first1=M. S.|last2=Denneberg|first2=T.|last3=Emanuelsson|first3=B.-M.|last4=Kågedal|first4=B.|last5=Lindgren|first5=S.|title=Pharmacokinetics of oral tiopronin|journal=European Journal of Clinical Pharmacology|date=August 1993|volume=45|issue=1|pages=79–84|doi=10.1007/BF00315354|pmid=8405034}} 4. ^{{cite journal|last1=Delecoeuillerie|first1=G|title=[Tolerability and therapeutic maintenance of tiopronin, new basic treatment of rheumatoid arthritis. Apropos of long-term follow-up of 268 cases].|journal=Revue du Rhumatisme et des Maladies Osteo-articulaires|date=30 April 1989|volume=56|issue=5 Pt 2|pages=38–42|pmid=2740804}} 5. ^{{cite journal|last1=Pasero|first1=Giampiero|last2=Pellegrini|first2=Pietro|last3=Ambanelli|first3=Umberto|last4=Ciompi|first4=Maria Laura|last5=Colamussi|first5=Vincenzo|last6=Ferraccioli|first6=Gianfranco|last7=Barbieri|first7=Paola|last8=Mazzoni|first8=Maria Rosa|last9=Menegale|first9=Germano|last10=Trippi|first10=Donatella|title=Controlled multicenter trial of tiopronin and D-penicillamine for rheumatoid arthritis|journal=Arthritis & Rheumatism|date=August 1982|volume=25|issue=8|pages=923–929|doi=10.1002/art.1780250803}} 6. ^{{cite journal |author1=Jennifer A. Dahl |author2=Bettye L. S. Maddux |author3=James E. Hutchison |last-author-amp=yes | title = Toward Greener Nanosynthesis | journal = Chemical Reviews | volume = 107 | issue = 6 | pages = 2228–2269 | year = 2007 | doi = 10.1021/cr050943k | pmid = 17564480}} 7. ^{{cite journal|last1=Jaffe|first1=Israeli A.|title=Adverse effects profile of sulfhydryl compounds in man|journal=The American Journal of Medicine|date=March 1986|volume=80|issue=3|pages=471–476|doi=10.1016/0002-9343(86)90722-9}} 8. ^{{cite news|last1=Lowe|first1=Derek|title=The Most Unconscionable Drug Price Hike I Have Yet Seen|url=http://blogs.sciencemag.org/pipeline/archives/2014/09/11/the_most_unconscionable_drug_price_hike_i_have_yet_seen|work=In the Pipeline|date=11 September 2014}} 9. ^{{cite web|url=http://www.fiercebiotech.com/story/why-would-martin-shkreli-hike-old-drug-price-5000-only-moron-would-ask/2015-09-20|title=Why would Martin Shkreli hike an old drug price by 5000%? Only a 'moron' would ask|work=FierceBiotech|first=John |last=Carroll |date=September 20, 2015}} 10. ^{{cite news|last1=Elvidge|first1=Suzanne|title=Imprimis shuts down Texas plant, axes 8% of jobs|url=https://www.biopharmadive.com/news/imprimis-shuts-down-texas-plant-axes-8-of-jobs/427296/|work=BioPharma Dive|date=September 29, 2016}} External links
3 : Orphan drugs|Thiols|Amino acid derivatives |
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