D-(-)-Penicillamine

CAS No. 52-67-5

D-(-)-Penicillamine( NSC 81549 | D-Penicillamine | β-Thiovaline )

Catalog No. M14865 CAS No. 52-67-5

(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid is the most characteristic degradation product of the penicillin antibiotics.

Purity : >98% (HPLC)

COA Datasheet HNMR HPLC MSDS Handing Instructions
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Biological Information

  • Product Name
    D-(-)-Penicillamine
  • Note
    Research use only, not for human use.
  • Brief Description
    (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid is the most characteristic degradation product of the penicillin antibiotics.
  • Description
    (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. Target: Others (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid (Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. (In Vitro):Penicillamine (D-(-)-Penicillamine) (5 mg; 7 d; CD4+ and CD+ splenocytes) promotes cellular immune responses.(In Vivo):Penicillamine (D-(-)-Penicillamine) (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases serum free copper concentration.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases ATP7A and CTR1 mRNA expression in the brain of tx mice.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) induces oxidative-stress in the central nervous system.Penicillamine (0.1-250 mg/kg; i.p.; once, for 90 min; male NMRI mice) has binaural phase effect on seizure.Penicillamine (5 mg/kg; i.v.; daily, for 8 weeks; male BN rats) prevents the onset of autoimmunity at a low dose.
  • In Vitro
    Penicillamine (D-(-)-Penicillamine) (5 mg; 7 d; CD4+ and CD+ splenocytes) promotes cellular immune responses. Western Blot Analysis Cell Line:CD4+ and CD+ splenocytes Concentration:5 mg Incubation Time:7 days Result:Increased IL-4 and IFN-γ mRNA expression in response to high dose treatment and remained high in both CD4+ and CD+ splenocytes.
  • In Vivo
    Penicillamine (D-(-)-Penicillamine) (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases serum free copper concentration.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases ATP7A and CTR1 mRNA expression in the brain of tx mice.Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) induces oxidative-stress in the central nervous system.Penicillamine (0.1-250 mg/kg; i.p.; once, for 90 min; male NMRI mice) has binaural phase effect on seizure.Penicillamine (5 mg/kg; i.v.; daily, for 8 weeks; male BN rats) prevents the onset of autoimmunity at a low dose. Animal Model:Toxic milk mutant mice (tx mice) and DL mice Dosage:200 mg/kg Administration:Oral gavage; daily, for 3, 10 and 14 days Result:Increased the free copper concentrations in the tx mice serum on the 3rd day.Animal Model:Toxic milk mutant mice (tx mice) and DL mice Dosage:200 mg/kg Administration:Oral gavage; daily, for 3, 10 and 14 days Result:Increased the mRNA expression of ATP7A by 4-fold. Increased CTR1 mRNA expression by 6.9-fold in the cortex and 9.1-fold in the basal ganglia of tx mice.Animal Model:Toxic milk mutant mice (tx mice) and DL mice Dosage:200 mg/kg Administration:Oral gavage; daily, for 3, 10 and 14 daysResult:Increased the concentration of MDA and decreased GSH/GSSG ratios through nitric oxide/NMDA pathways.Animal Model:Male NMRI miceDosage:0.1, 0.5, 1, 10, 100, 150 and 250 mg/kg Administration:Intraperitoneal injection; once, for 90 minutesResult:Had anticonvulsant effects at a low dose (0.5 mg/kg) and had anticonvulsant effects at a high dose (250 mg/kg). Reversed the anti- and proconvulsant effects by acute pretreatment of L-NAME (a nonselective nitric oxide synthase inhibitor) and 7-NI (a selective neuronal nitric oxide synthase inhibitor).Animal Model:Male BN rats Dosage:5 mg/kg Administration:Intravenous injection; daily, for 8 weeks Result:Inhibited IgE upregulation and prevented the onset of autoimmunity.
  • Synonyms
    NSC 81549 | D-Penicillamine | β-Thiovaline
  • Pathway
    Others
  • Target
    Other Targets
  • Recptor
    Copper
  • Research Area
    Inflammation/Immunology
  • Indication
    ——

Chemical Information

  • CAS Number
    52-67-5
  • Formula Weight
    149.21
  • Molecular Formula
    C5H11NO2S
  • Purity
    >98% (HPLC)
  • Solubility
    Water: 30 mg/mL (201.05 mM)
  • SMILES
    CC(C)([C@H](C(=O)O)N)S
  • Chemical Name
    (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

Shipping & Storage Information

  • Storage
    (-20℃)
  • Shipping
    With Ice Pack
  • Stability
    ≥ 2 years

Reference

1. Brewer GJ. Expert Opin PharmacOthers. 2006 Feb;7(3):317-24.
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