Tiopronin

WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571443

CAS#: 1953-02-2

Description: Tiopronin is the sulfhydryl-acylated derivative of glycine. It is used to treat cystinuria and hepatic cell injury, but may give rise to rare complications such as proteinuria and nephrotic syndrome.

Chemical Structure

Tiopronin

CAS# 1953-02-2

Instruction

Theoretical Analysis

MedKoo Cat#: 571443
Name: Tiopronin
CAS#: 1953-02-2
Chemical Formula: C5H9NO3S
Exact Mass: 163.03
Molecular Weight: 163.190
Elemental Analysis: C, 36.80; H, 5.56; N, 8.58; O, 29.41; S, 19.65

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 225
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Tiopronin; Acadione; Capen; Epatiol; Vincol

IUPAC/Chemical Name: Glycine, N-(2-mercapto-1-oxopropyl)- (9CI)

InChi Key: YTGJWQPHMWSCST-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)

SMILES Code: O=C(O)CNC(C(S)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 163.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zheng Z, Xue Y, Jia J, Wei L, Shang W, Lin S. Tiopronin-induced membranous nephropathy: a case report. Ren Fail. 2014 Oct;36(9):1455-60. doi: 10.3109/0886022X.2014.926754. Epub 2014 Jul 16. PubMed PMID: 25026975.

2: Kong D, Huang X, Lin B, Jiang J, Li Q, Wei Q, Chi Y, Chen G. Determination of tiopronin based on the enhancement of Ru(bpy)₅²⁺ co-reactant electrochemiluminescence. Talanta. 2015 Mar;134:524-9. doi: 10.1016/j.talanta.2014.11.043. Epub 2014 Nov 29. PubMed PMID: 25618703.

3: Valachová K, Baňasová M, Topoľská D, Sasinková V, Juránek I, Collins MN, Šoltés L. Influence of tiopronin, captopril and levamisole therapeutics on the oxidative degradation of hyaluronan. Carbohydr Polym. 2015 Dec 10;134:516-23. doi: 10.1016/j.carbpol.2015.07.029. Epub 2015 Jul 19. PubMed PMID: 26428153.

4: Tang MC, Cheng L, Qiu L, Jia RG, Sun RQ, Wang XP, Hu GY, Zhao Y. Efficacy of Tiopronin in treatment of severe non-alcoholic fatty liver disease. Eur Rev Med Pharmacol Sci. 2014;18(2):160-4. PubMed PMID: 24488902.

5: Huo S, Shi H, Liu D, Shen S, Zhang J, Song C, Shi T. Kinetics and mechanism of reactions of the drug tiopronin with platinum(IV) complexes. J Inorg Biochem. 2013 Aug;125:9-15. doi: 10.1016/j.jinorgbio.2013.04.003. Epub 2013 Apr 19. PubMed PMID: 23665090.

6: Hall MD, Marshall TS, Kwit AD, Miller Jenkins LM, Dulcey AE, Madigan JP, Pluchino KM, Goldsborough AS, Brimacombe KR, Griffiths GL, Gottesman MM. Inhibition of glutathione peroxidase mediates the collateral sensitivity of multidrug-resistant cells to tiopronin. J Biol Chem. 2014 Aug 1;289(31):21473-89. doi: 10.1074/jbc.M114.581702. Epub 2014 Jun 14. PubMed PMID: 24930045; PubMed Central PMCID: PMC4118110.

7: Cui L, Zahedi P, Saraceno J, Bristow R, Jaffray D, Allen C. Neoplastic cell response to tiopronin-coated gold nanoparticles. Nanomedicine. 2013 Feb;9(2):264-73. doi: 10.1016/j.nano.2012.05.016. Epub 2012 Jun 9. PubMed PMID: 22687897.

8: Baghayeri M, Maleki B, Zarghani R. Voltammetric behavior of tiopronin on carbon paste electrode modified with nanocrystalline Fe₅₀Ni₅₀ alloys. Mater Sci Eng C Mater Biol Appl. 2014 Nov;44:175-82. doi: 10.1016/j.msec.2014.08.023. Epub 2014 Aug 12. PubMed PMID: 25280694.

9: Prokopovich P, Leech R, Carmalt CJ, Parkin IP, Perni S. A novel bone cement impregnated with silver-tiopronin nanoparticles: its antimicrobial, cytotoxic, and mechanical properties. Int J Nanomedicine. 2013;8:2227-37. doi: 10.2147/IJN.S42822. Epub 2013 Jun 18. PubMed PMID: 23818779; PubMed Central PMCID: PMC3693822.

10: Prado-Gotor R, Grueso E. Noncovalent interactions of tiopronin-protected gold nanoparticles with DNA: two methods to quantify free energy of binding. ScientificWorldJournal. 2014 Jan 22;2014:143645. doi: 10.1155/2014/143645. eCollection 2014. PubMed PMID: 24587710; PubMed Central PMCID: PMC3920862.

11: Bao QY, Geng DD, Xue JW, Zhou G, Gu SY, Ding Y, Zhang C. Glutathione-mediated drug release from Tiopronin-conjugated gold nanoparticles for acute liver injury therapy. Int J Pharm. 2013 Mar 25;446(1-2):112-8. doi: 10.1016/j.ijpharm.2013.01.073. Epub 2013 Feb 14. PubMed PMID: 23416166.

12: Yuan B, Zhai N, Jiang X, Jin Y, Liu C, Li C, Xu H. Quantitative determination of tiopronin in human plasma by LC-MS/MS without derivatization. Biomed Chromatogr. 2012 Jul;26(7):839-43. doi: 10.1002/bmc.1738. Epub 2011 Nov 4. PubMed PMID: 22052743.

13: Kim GH, Kellner CP, Hickman ZL, Zacharia BE, Starke RM, Hwang BY, Ducruet AF, Fernandez L, Mayer SA, Tracey KJ, Connolly ES Jr. A phase I clinical trial of tiopronin, a putative neuroprotective agent, in aneurysmal subarachnoid hemorrhage. Neurosurgery. 2010 Jul;67(1):182-5; discussion 186. doi: 10.1227/01.NEU.0000370919.93259.3C. PubMed PMID: 20559104; PubMed Central PMCID: PMC4540229.

14: Tasic V, Lozanovski VJ, Ristoska-Bojkovska N, Sahpazova E, Gucev Z. Nephrotic syndrome occurring during tiopronin treatment for cystinuria. Eur J Pediatr. 2011 Feb;170(2):247-9. doi: 10.1007/s00431-010-1315-3. Epub 2010 Oct 6. PubMed PMID: 20924604.

15: Lindell A, Denneberg T, Jeppsson JO. Urinary excretion of free cystine and the tiopronin-cysteine-mixed disulfide during long term tiopronin treatment of cystinuria. Nephron. 1995;71(3):328-42. PubMed PMID: 8569983.

16: Chen Z, Wang Z, Chen J, Gao W. Label-free fluorescence turn on detection of tiopronin with tunable dynamic range based on the ensemble of Alizarin Red S/copper ion. Talanta. 2012 Sep 15;99:774-9. doi: 10.1016/j.talanta.2012.07.021. Epub 2012 Jul 16. PubMed PMID: 22967623.

17: Miyajima A, Bamba M, Onohara T, Hirota T. Effect of tiopronin on excretion of homocysteine and its plasma exposure level in rats. Drug Metab Pharmacokinet. 2016 Jun;31(3):249-51. doi: 10.1016/j.dmpk.2016.03.002. Epub 2016 Mar 17. PubMed PMID: 27155909.

18: Cai X, Chen HH, Wang CL, Chen ST, Lai SF, Chien CC, Chen YY, Kempson IM, Hwu Y, Yang CS, Margaritondo G. Imaging the cellular uptake of tiopronin-modified gold nanoparticles. Anal Bioanal Chem. 2011 Aug;401(3):809-16. doi: 10.1007/s00216-011-4986-3. Epub 2011 May 3. PubMed PMID: 21537916.

19: Goldsborough AS, Handley MD, Dulcey AE, Pluchino KM, Kannan P, Brimacombe KR, Hall MD, Griffiths G, Gottesman MM. Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin. J Med Chem. 2011 Jul 28;54(14):4987-97. doi: 10.1021/jm2001663. Epub 2011 Jun 24. PubMed PMID: 21657271; PubMed Central PMCID: PMC3208667.

20: Wang H, Ma C, Zhou J, Liu XQ. Stereoselective analysis of tiopronin enantiomers in rat plasma using high-performance liquid chromatography-electrospray ionization mass spectrometry after chiral derivatization. Chirality. 2009 May;21(5):531-8. doi: 10.1002/chir.20634. PubMed PMID: 18655161.

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