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P4875

Sigma-Aldrich

D-Penicillamine

98-101%

Sinônimo(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

Fórmula linear:
(CH3)2C(SH)CH(NH2)CO2H
Número CAS:
52-67-5
Peso molecular:
149.21
Beilstein:
1722375
Número CE:
200-148-8
Número MDL:
MFCD00064302
Código UNSPSC:
51202303
ID de substância PubChem:
24898564
NACRES:
NA.76

Nível de qualidade

100

Ensaio

98-101%

forma

powder

pf

210 °C (dec.) (lit.)

solubilidade

H2O: 100 mg/mL

Modo de ação

cell wall synthesis | interferes

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

VVNCNSJFMMFHPL-VKHMYHEASA-N

Informações sobre genes

mouse ... Oprk1(18387)

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Descrição geral

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

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Outras notas

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

Pictogramas

Health hazard
GHS08

Palavra indicadora

Warning

Frases de perigo

H361d

Classificações de perigo

Repr. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Molecular pharmacology, 50(3), 501-505 (1996-09-01)
D-Penicillamine (beta, beta-dimethyl cysteine) is an antirheumatic thiol drug with a poorly understood mechanism of action. On the basis that gold(I) thiolates and D-penicillamine are both capable of forming stable bonds with endogenous thiols, we sought a common target of
P Jaffray et al.
Annals of the rheumatic diseases, 43(2), 333-338 (1984-04-01)
The long-acting antirheumatic drug D-penicillamine was found to inhibit the growth of asynchronous cultures of rabbit articular chondrocytes. This inhibitory effect was dose-related between 5 X 10(-4) M and 5 X 10(-3) M and was time-dependent for a given dose.
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