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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
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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[1] and to inhibit the growth of asynchronous cultures of rabbit articular chondrocytes[2].

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.

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1 of 1

This Item
196312D9378P1101
D-Penicillamine 98-101%

Sigma-Aldrich

P4875

D-Penicillamine

L-Penicillamine 99%

Sigma-Aldrich

196312

L-Penicillamine

3,4-Dihydroxy-D-phenylalanine powder, ≥95%

Sigma-Aldrich

D9378

3,4-Dihydroxy-D-phenylalanine

D-Penicillamine disulfide 97%

Sigma-Aldrich

P1101

D-Penicillamine disulfide

mode of action

cell wall synthesis | interferes

mode of action

-

mode of action

-

mode of action

-

form

powder

form

powder

form

powder

form

powder or crystals

assay

98-101%

assay

99%

assay

≥95%

assay

97%

solubility

H2O: 100 mg/mL

solubility

-

solubility

1 M HCl: soluble, ethanol: insoluble

solubility

-

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

storage temp.

-

Gene Information

mouse ... Oprk1(18387)

Gene Information

-

Gene Information

-

Gene Information

-

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000381015
0000381015
STBL1265
STBK5704
STBK4593

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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.
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.
Maria C Fernandez et al.
Molecular human reproduction, 25(12), 787-796 (2019-10-28)
Peroxiredoxins (PRDXs) are antioxidant enzymes proven to control the levels of reactive oxygen species (ROS) and to avoid oxidative damage in the spermatozoon. Previously, we have shown that low amounts of PRDXs are associated with male infertility and that PRDX6
View All Related Papers

Global Trade Item Number

SKUGTIN
P4875-1G04061834375296
P4875-25G04061834375302
P4875-5G04061834375319

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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