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P4875

Sigma-Aldrich

D-Penicillamine

98-101%

Synonym(s):

3,3-Dimethyl-D-cysteine, 3-Mercapto-D-valine, D-(−)-2-Amino-3-mercapto-3-methylbutanoic acid

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About This Item

Linear Formula:
(CH3)2C(SH)CH(NH2)CO2H
CAS Number:
Molecular Weight:
149.21
Beilstein:
1722375
EC Number:
MDL number:
UNSPSC Code:
51202303
PubChem Substance ID:
NACRES:
NA.76

Quality Level

Assay

98-101%

form

powder

mp

210 °C (dec.) (lit.)

solubility

H2O: 100 mg/mL

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

CC(C)(S)[C@@H](N)C(O)=O

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

Gene Information

mouse ... Oprk1(18387)

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General description

D-Penicillamine is derived from the hydrolysis of the corresponding beta-lactam antibiotic.

Application

It is used as an antirheumatic and as a chelating agent in Wilson′s disease. It is used as a copper chelator to form mixed disulfides with cysteine or other sulfide media components. It is used to inactivate protein-1 DNA binding and to inhibit the growth of asynchronous cultures of rabbit articular chondrocytes.

Biochem/physiol Actions

Penicillamine is a characteristic degradation product of penicillin type antibiotics. One atom of copper combines with two molecules of penicillamine. Penicillamine reduces excess cystine excretion in cystinuria. This is by disulfide interchange between penicillamine and cystine, which results in formation of a readily excreted penicillamine-cysteine disulfide. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. Penicillamine lowers IgM rheumatoid factor and depresses T-cell activity.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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