An antioxidant
Related Products
Labeled Version(s)
33376Tiopronin-d3
Metabolite(s)
39020Tiopronin-Cysteine Disulfide
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Tiopronin

Item No. 23720

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-mercapto-1-oxopropyl)-glycine
CAS Number
1953-02-2
Synonyms
  • BRN 1859822
  • (±)-Tiopronin
Molecular Formula
C5H9NO3S
Formula Weight
163.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly SolubleMethanol: Slightly Soluble
SMILES
OC(CNC(C(S)C)=O)=O
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)
InChi Key
YTGJWQPHMWSCST-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 g

    $36

    Add

    5 g

    $95

    Add
    Cayman Chemical
    Explore Obesity & Metabolic Disease Resources

    Discover high-quality research tools to investigate GLP-1 mechanisms and next-generation metabolic targets.

    OBESITY RESEARCH SOLUTIONS
    Product Description

    Tiopronin is an antioxidant.1,2,3,4,5 It reduces free radical production by murine macrophages and granulocytes in vitro.1 Tiopronin increases hypoxia-inducible factor-1α (HIF-1α) and VEGF levels in HCT116 cells and reduces myeloperoxidase (MPO) activity and colon pro-inflammatory cytokine production in a rat model of colitis.2 Tiopronin also reduces the incidence of cleft palate in fetuses born to female mice exposed to teratogenic methylmercury chloride.3 Tiopronin (100 mg/kg) decreases lipid peroxidation and transverse aortic constriction in a mouse model of cardiac hypertrophy.4 Tiopronin is hepatoprotective in a rat model of non-alcoholic steatohepatitis (NASH) via increasing superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities and reversing hepatocyte degeneration.5 It has been associated with membranous nephropathy.6 Formulations containing tiopronin have been used in the treatment of cystinuria, an inborn error of metabolism characterized by kidney stones and excessive urinary excretion of cysteine, arginine, ornithine, and lysine.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rommain, M., Delecoeuillerie, G., Paul, J.L., et al. Inhibitory action of tiopronin on free radicals. Rev. Rhum. Mal. Osteoartic. 56(5 Pt 2), 34-37 (1989).

    2. Yum, S., Park, H., Hong, S., et al. N-(2-mercaptopropionyl)-glycine, a diffusible antioxidant, activates HIF-1 by inhibiting HIF prolyl hydroxylase-2: Implication in amelioration of rat colitis by the antioxidant. Biochem. Biophys. Res. Commun. 443(3), 1008-1013 (2014).

    3. Fujimoto, T., Fuyuta, M., Kiyofuji, E., et al. Prevention by tiopronin (2-mercaptopropionyl glycine) of methylmercuric chloride-induced teratogenic and fetotoxic effects in mice. Teratology 20(2), 297-301 (1979).

    4. Date, M.O., Morita, T., Yamashita, N., et al. The antioxidant N-2-mercaptopropionyl glycine attenuates left ventricular hypertrophy in in vivo murine pressure-overload model. J. Am. Coll. Cardiol. 39(5), 907-912 (2002).

    5. Wang, J.Q., Zou, Y.H., Huang, C., et al. Protective effects of tiopronin against high fat diet-induced non-alcoholic steatohepatitis in rats. Acta Pharmacol. Sin. 33(6), 791-797 (2012).

    6. Micallef, S., Delicata, L., Agius, J.F., et al. Tiopronin-induced membranous nephropathy in a patient with refractory familial cystinuria. Br. J. Hosp. Med. (Lond). 83(8), 1-4 (2022).