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:
Molecular Weight:
149.21
UNSPSC Code:
51202303
NACRES:
NA.76
PubChem Substance ID:
EC Number:
200-148-8
Beilstein/REAXYS Number:
1722375
MDL number:
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)
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.
signalword
Warning
hcodes
Hazard Classifications
Repr. 2
Storage Class
11 - Combustible Solids
wgk
WGK 2
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| P4875-1G | 04061834375296 |
| P4875-25G | 04061834375302 |
| P4875-5G | 04061834375319 |