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P4875

Sigma-Aldrich

D-Penicillamine

98-101%

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Synonym(s):
3,3-Dimethyl-D-cysteine, 3-Mercapto-D-valine, D-(−)-2-Amino-3-mercapto-3-methylbutanoic acid
Linear Formula:
(CH3)2C(SH)CH(NH2)CO2H
CAS Number:
Molecular Weight:
149.21
Beilstein/REAXYS Number:
1722375
EC Number:
MDL number:
UNSPSC Code:
51101500
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

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

wgk_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Annals of the rheumatic diseases, 43(2), 333-338 (1984-04-01)
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