An internal standard for the quantification of tiopronin
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Unlabeled Version(s)
23720Tiopronin
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Tiopronin-d3

Item No. 33376

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-mercapto-1-oxopropyl-3,3,3-d3)-glycine
CAS Number
1189700-74-0
Synonyms
  • (±)-Tiopronin-d3
Molecular Formula
C5H6D3NO3S
Formula Weight
166.2
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: SolubleWater: Soluble
SMILES
OC(CNC(C(S)C([2H])([2H])[2H])=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)/i1D3
InChi Key
YTGJWQPHMWSCST-FIBGUPNXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $202

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    5 mg

    $797

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    Cayman Chemical
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    Product Description

    Tiopronin-d3 is intended for use as an internal standard for the quantification of tiopronin (Item No. 23720) by GC- or LC-MS. 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).