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P4875

Sigma-Aldrich

D-Penicillamine

98-101%

Synonyme(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

Formule linéaire :
(CH3)2C(SH)CH(NH2)CO2H
Numéro CAS:
52-67-5
Poids moléculaire :
149.21
Numéro Beilstein :
1722375
Numéro CE :
200-148-8
Numéro MDL:
MFCD00064302
Code UNSPSC :
51202303
ID de substance PubChem :
24898564
Nomenclature NACRES :
NA.76

Niveau de qualité

100

Pureté

98-101%

Forme

powder

Pf

210 °C (dec.) (lit.)

Solubilité

H2O: 100 mg/mL

Mode d’action

cell wall synthesis | interferes

Température de stockage

2-8°C

Chaîne 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

Clé InChI

VVNCNSJFMMFHPL-VKHMYHEASA-N

Informations sur le gène

mouse ... Oprk1(18387)

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Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361d

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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.
Hao Ren et al.
Microorganisms, 7(12) (2019-12-15)
Probiotics and phytobiotics have been studied as in-feed antibiotic alternatives for decades, yet there are no studies on their possible symbiotic effects. In the present study, newly hatched chickens were fed with feeds supplemented either with host-specific Lactobacillus strains (L.
M L Handel et al.
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
R John Aitken et al.
Biology of reproduction, 87(5), 110-110 (2012-08-31)
The prolonged incubation of human spermatozoa in vitro was found to induce a loss of motility associated with the activation of mitochondrial reactive oxygen species generation in the absence of any change in mitochondrial membrane potential. The increase in mitochondrial
Wenge Jiang et al.
Nature communications, 10(1), 2318-2318 (2019-05-28)
Since Pasteur first successfully separated right-handed and left-handed tartrate crystals in 1848, the understanding of how homochirality is achieved from enantiomeric mixtures has long been incomplete. Here, we report on a chirality dominance effect where organized, three-dimensional homochiral suprastructures of
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