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Merck

P4875

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:
52-67-5
Molecular Weight:
149.21
UNSPSC Code:
51202303
NACRES:
NA.76
PubChem Substance ID:
24898564
EC Number:
200-148-8
Beilstein/REAXYS Number:
1722375
MDL number:
MFCD00064302

Key Documents

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InChI key

VVNCNSJFMMFHPL-VKHMYHEASA-N

InChI

1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

SMILES string

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

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

Quality Level

100

Gene Information

mouse ... Oprk1(18387)

Related Categories

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
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

P4875-5G: + P4875-25G: + P4875-100G: + P4875-VAR: + P4875-BULK: + P4875-1G: + P4875-500MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000381015
0000381015
STBL1265
STBK5704
STBK4593

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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
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
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.
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
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