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
Beilstein:
1722375
EC Number:
MDL number:
UNSPSC Code:
51202303
PubChem Substance ID:
NACRES:
NA.76
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Repr. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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