A chelating agent
Related Products
Labeled Version(s)
33797Penicillamine-d3
Metabolite(s)
36297S-Methyl-D-penicillamine
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D-Penicillamine

Item No. 23955

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-mercapto-D-valine
CAS Number
52-67-5
Synonyms
  • NSC 81549
  • β-Thiovaline
Molecular Formula
C5H11NO2S
Formula Weight
149.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:7): 0.12 mg/mlEthanol: 5 mg/ml
SMILES
O=C(O)[C@@H](C(C)(C)S)N
InChi Code
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChi Key
VVNCNSJFMMFHPL-VKHMYHEASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 g

    $29

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    5 g

    $63

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    10 g

    $108

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    Product Description

    D-Penicillamine is an orally bioavailable copper chelator and penicillin degradation product.1,2 It increases urinary and fecal copper excretion and decreases liver copper concentration in a rat model of copper overload when administered at 0.67 mmol/kg per day, but does not affect kidney, spleen, or brain copper levels.3 D-Penicillamine (100 mg/kg per day) dissolves copper-rich granules in hepatic lysosomes of Long-Evans cinnamon (LEC) rats, which spontaneously develop hepatic injury and acute hepatitis and have a mutation homologous to that of the human Wilson disease gene.4 D-Penicillamine has anticonvulsant and proconvulsant effects in mice when administered at 0.5 and 250 mg/kg, respectively, which are blocked by the nitric oxide synthase (NOS) inhibitors L-NAME (Item No. 80210) and 7-nitroindazole (Item No. 81340).5 Formulations containing D-penicillamine have been used to treat Wilson disease, cystinuria, and active rheumatoid arthritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Delangle, P., and Mintz, E. Chelation therapy in Wilson’s disease: From D-penicillamine to the design of selective bioinspired intracellular Cu(I) chelators. Dalton Trans. 41(21), 6359-6370 (2012).

    2. Abraham, E.P., Chain, E., Baker, W., et al. Penicillamine, a characteristic degradation product of penicillin. Nature 151(3821), 107 (1943).

    3. Domingo, J.L., Gómez, M., and Jones, M.M. Comparative efficacy of several potential treatments for copper mobilization in copper-overloaded rats. Biol. Trace Elem. Res. 74(2), 127-139 (2000).

    4. Klein, D., Lichtmannegger, J., Heinzmann, U., et al. Dissolution of copper-rich granules in hepatic lysosomes by D-penicillamine prevents the development of fulminant hepatitis in Long-Evans cinnamon rats. J. Hepatol. 32(2), 193-201 (2000).

    5. Rahimi, N., Sadeghzadeh, M., Javad-Paydar, M., et al. Effects of D-penicillamine on pentylenetetrazole-induced seizures in mice: involvement of nitric oxide/NMDA pathways. Epilepsy Behav. 39, 42-47 (2014).