Tiopronin-d3
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MedKoo CAT#: 464684

CAS#: 1189700-74-0

Description: Tiopronin-d3 is intended for use as an internal standard for the quantification of tiopronin by GC- or LC-MS. Tiopronin is an antioxidant that has diverse biological activities. It reduces free radical production by murine macrophages and granulocytes in vitro in a dose-dependent manner. Tiopronin induces expression of hypoxia-inducible factor 1α (HIF-1α) and increases VEGF secretion in human colon carcinoma cells.2 Rectal administration (500 μl of a 10 mM solution) reduces myeloperoxidase activity and reduces pro-inflammatory cytokine production in the colon in a rat model of colitis. Tiopronin (80-320 mg/kg per day) reduces the incidence of cleft palate in fetuses born to female mice orally exposed to teratogenic methylmercury chloride. Tiopronin (100 mg/kg) reduces heme oxygenase 1 mRNA expression, lipid peroxidation, and transverse aortic constriction in a mouse model of cardiac hypertrophy. Tiopronin (20 mg/kg) is hepatoprotective, increasing activity of the antioxidant enzymes superoxide dismutase and glutathione peroxidase and reversing hepatocyte degeneration in a rat model of high-fat diet-induced non-alcoholic steatohepatitis.

Chemical Structure

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Tiopronin-d3
CAS# 1189700-74-0
Instruction

Theoretical Analysis

MedKoo Cat#: 464684
Name: Tiopronin-d3
CAS#: 1189700-74-0
Chemical Formula: C5H6D3NO3S
Exact Mass: 166.05
Molecular Weight: 166.209
Elemental Analysis: C, 36.13; H, 7.27; N, 8.43; O, 28.88; S, 19.29

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
25mg USD -2 2 Weeks
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
1mg USD 330 2 Weeks
5mg USD 890 2 Weeks
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Synonym: Tiopronin-d3; Tiopronin d3; (±) Tiopronin-d3; (±)-Tiopronin-d3;

IUPAC/Chemical Name: (2-mercaptopropanoyl-3,3,3-d3)glycine

InChi Key: YTGJWQPHMWSCST-FIBGUPNXSA-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)/i1D3

SMILES Code: OC(CNC(C(C([2H])([2H])[2H])S)=O)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 166.21 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.

Recalculate based on batch purity %
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: Zhang H, Yang K, Cheng Z, Thomas C, Steinbrunner A, Pryor C, Vulcan M, Kemp C, Orea D, Paththamperuma C, Chen AY, Cohen SM, Page RC, Tierney DL, Crowder MW. Spectroscopic and biochemical characterization of metallo-β-lactamase IMP-1 with dicarboxylic, sulfonyl, and thiol inhibitors. Bioorg Med Chem. 2021 May 1;40:116183. doi: 10.1016/j.bmc.2021.116183. Epub ahead of print. PMID: 33965839.

2: Prot-Bertoye C, Daudon M, Tostivint I, Dousseaux MP, Defazio J, Traxer O, Knebelmann B, Courbebaisse M. Cystinurie [Cystinuria]. Nephrol Ther. 2021 Apr;17S:S100-S107. French. doi: 10.1016/j.nephro.2020.03.001. PMID: 33910689.

3: Lu Y, Bohn-Wippert K, Pazerunas PJ, Moy JM, Singh H, Dar RD. Screening for gene expression fluctuations reveals latency-promoting agents of HIV. Proc Natl Acad Sci U S A. 2021 Mar 16;118(11):e2012191118. doi: 10.1073/pnas.2012191118. PMID: 33836565; PMCID: PMC7980449.

4: Deng J, Cong Y, Han X, Wei W, Lu Y, Liu T, Zhao W, Lin B, Luo Y, Zhang X. A liver-on-a-chip for hepatoprotective activity assessment. Biomicrofluidics. 2020 Nov 30;14(6):064107. doi: 10.1063/5.0024767. PMID: 33312328; PMCID: PMC7710384.

5: Niu H, Sanabria-Cabrera J, Alvarez-Alvarez I, Robles-Diaz M, Stankevičiūtė S, Aithal GP, Björnsson ES, Andrade RJ, Lucena MI. Prevention and management of idiosyncratic drug-induced liver injury: Systematic review and meta-analysis of randomised clinical trials. Pharmacol Res. 2021 Feb;164:105404. doi: 10.1016/j.phrs.2020.105404. Epub 2020 Dec 24. PMID: 33359912.

6: Shahid M, Subhan F, Islam NU, Ahmad N, Farooq U, Abbas S, Akbar S, Ullah I, Raziq N, Din ZU. Correction to: The antioxidant N-(2-mercaptopropionyl)-glycine (tiopronin) attenuates expression of neuropathic allodynia and hyperalgesia. Naunyn Schmiedebergs Arch Pharmacol. 2021 Mar;394(3):579. doi: 10.1007/s00210-020-02033-7. Erratum for: Naunyn Schmiedebergs Arch Pharmacol. 2020 Oct 20;: PMID: 33284400.

7: Cambra JM, Martinez CA, Rodriguez-Martinez H, Martinez EA, Cuello C, Gil MA. N-(2-mercaptopropionyl)-glycine enhances in vitro pig embryo production and reduces oxidative stress. Sci Rep. 2020 Oct 29;10(1):18632. doi: 10.1038/s41598-020-75442-6. PMID: 33122658; PMCID: PMC7596235.

8: Shahid M, Subhan F, Islam NU, Ahmad N, Farooq U, Abbas S, Akbar S, Ullah I, Raziq N, Din ZU. The antioxidant N-(2-mercaptopropionyl)-glycine (tiopronin) attenuates expression of neuropathic allodynia and hyperalgesia. Naunyn Schmiedebergs Arch Pharmacol. 2021 Apr;394(4):603-617. doi: 10.1007/s00210-020-01995-y. Epub 2020 Oct 20. Erratum in: Naunyn Schmiedebergs Arch Pharmacol. 2020 Dec 7;: PMID: 33079239.

9: Servais A, Thomas K, Dello Strologo L, Sayer JA, Bekri S, Bertholet-Thomas A, Bultitude M, Capolongo G, Cerkauskiene R, Daudon M, Doizi S, Gillion V, Gràcia- Garcia S, Halbritter J, Heidet L, van den Heijkant M, Lemoine S, Knebelmann B, Emma F, Levtchenko E; Metabolic Nephropathy Workgroup of the European Reference Network for Rare Kidney Diseases (ERKNet) and eUROGEN. Cystinuria: clinical practice recommendation. Kidney Int. 2021 Jan;99(1):48-58. doi: 10.1016/j.kint.2020.06.035. Epub 2020 Sep 9. PMID: 32918941.

10: Takubo H, Taniguchi T, Iwanaga K, Nomura Y. Evaluation of the changes in exposure to thiol compounds in chronic kidney disease patients using the PBPK model. Xenobiotica. 2021 Jan;51(1):31-39. doi: 10.1080/00498254.2020.1805816. Epub 2020 Aug 12. PMID: 32744915.

11: Thomas CA, Cheng Z, Yang K, Hellwarth E, Yurkiewicz CJ, Baxter FM, Fullington SA, Klinsky SA, Otto JL, Chen AY, Cohen SM, Crowder MW. Probing the mechanisms of inhibition for various inhibitors of metallo-β-lactamases VIM-2 and NDM-1. J Inorg Biochem. 2020 Sep;210:111123. doi: 10.1016/j.jinorgbio.2020.111123. Epub 2020 Jun 15. PMID: 32622213.

12: Fullington S, Cheng Z, Thomas C, Miller C, Yang K, Ju LC, Bergstrom A, Shurina BA, Bretz SL, Page RC, Tierney DL, Crowder MW. An integrated biophysical approach to discovering mechanisms of NDM-1 inhibition for several thiol- containing drugs. J Biol Inorg Chem. 2020 Aug;25(5):717-727. doi: 10.1007/s00775-020-01794-z. Epub 2020 Jun 4. PMID: 32500360; PMCID: PMC7415715.

13: Moussa M, Papatsoris AG, Abou Chakra M, Moussa Y. Update on cystine stones: current and future concepts in treatment. Intractable Rare Dis Res. 2020 May;9(2):71-78. doi: 10.5582/irdr.2020.03006. PMID: 32494553; PMCID: PMC7263987.

14: Beltz J, Chernatynskaya A, Pfaff A, Ercal N. Protective effects of tiopronin on oxidatively challenged human lung carcinoma cells (A549). Free Radic Res. 2020 May;54(5):319-329. doi: 10.1080/10715762.2020.1763332. Epub 2020 May 22. PMID: 32363952; PMCID: PMC7534955.

15: Assimos DG. Re: Assessment of Health-Related Quality of Life in Patients with Cystinuria on Tiopronin Therapy. J Urol. 2020 Jul;204(1):180. doi: 10.1097/JU.0000000000001053.02. Epub 2020 Apr 9. PMID: 32272045.

16: Cil O, Perwad F. α-Lipoic Acid (ALA) Improves Cystine Solubility in Cystinuria: Report of 2 Cases. Pediatrics. 2020 May;145(5):e20192951. doi: 10.1542/peds.2019-2951. Epub 2020 Apr 3. PMID: 32245805.

17: Hall MD, Marshall TS, Kwit ADT, Miller Jenkins LM, Dulcey AE, Madigan JP, Pluchino KM, Goldsborough AS, Brimacombe KR, Griffiths GL, Gottesman MM. Correction: Inhibition of glutathione peroxidase mediates the collateral sensitivity of multidrug-resistant cells to tiopronin. J Biol Chem. 2020 Mar 27;295(13):4370. doi: 10.1074/jbc.AAC120.013256. Erratum for: J Biol Chem. 2014 Aug 1;289(31):21473-89. PMID: 32221035; PMCID: PMC7105309.

18: Melessen IM, Henderickx MM, Merkx MM, van Etten-Jamaludin FS, Homan van der Heide JJ, Kamphuis GM. The effect of additional drug therapy as metaphylaxis in patients with cystinuria: a systematic review. Minerva Urol Nefrol. 2020 Aug;72(4):427-440. doi: 10.23736/S0393-2249.20.03704-2. Epub 2020 Feb 19. PMID: 32083421.

19: Eisner BH, Goldfarb DS, Baum MA, Langman CB, Curhan GC, Preminger GM, Lieske JC, Pareek G, Thomas K, Zisman AL, Papagiannopoulos D, Sur RL. Evaluation and Medical Management of Patients with Cystine Nephrolithiasis: A Consensus Statement. J Endourol. 2020 Nov;34(11):1103-1110. doi: 10.1089/end.2019.0703. Epub 2020 Apr 6. PMID: 32066273; PMCID: PMC7869875.

20: Valachova K, Svik K, Biro C, Soltes L. Skin wound healing with composite biomembranes loaded by tiopronin or captopril. J Biotechnol. 2020 Feb 20;310:49-53. doi: 10.1016/j.jbiotec.2020.02.001. Epub 2020 Feb 3. PMID: 32027945.