Cas no 20902-45-8 (D-Penicillamine Disulfide)

D-Penicillamine Disulfide is a dimeric form of D-penicillamine, characterized by its disulfide bond formation. This compound is primarily utilized in biochemical and pharmaceutical research due to its role as a chelating agent and its ability to modulate thiol-disulfide exchange reactions. Its stability in the oxidized state makes it suitable for studies involving redox processes and metal ion interactions. The disulfide linkage enhances its resistance to reductive degradation, ensuring consistent performance in experimental applications. D-Penicillamine Disulfide is particularly valuable in investigating heavy metal detoxification, rheumatoid arthritis treatments, and cysteine metabolism pathways. Its well-defined chemical properties and high purity make it a reliable reagent for controlled laboratory use.
D-Penicillamine Disulfide structure
D-Penicillamine Disulfide structure
Product Name:D-Penicillamine Disulfide
CAS No:20902-45-8
MF:C10H20N2O4S2
MW:296.406800270081
MDL:MFCD00004264
CID:258346
PubChem ID:329750679
Update Time:2025-10-31

D-Penicillamine Disulfide Chemical and Physical Properties

Names and Identifiers

    • Penicillamine Disulfide
    • Penicillamine disulfide D-form
    • D-Penicillamine Disulfide
    • PENICILLAMINE DISULFIDE , USP STANDARD
    • 3,3''-Dithiobis-D-valine
    • 3,3'-dithiodi-D-valine
    • d-3,3-dimethyl cysteine disulphide
    • D-PENICILLAMINE DISULPHIDE
    • penicillamine disulphide
    • penicillinamine disulfide
    • 3,3′-Dithiodi-D-valine
    • 3,3′-Dithiobis-D-valine
    • NSC 87505
    • Epitope ID:140793
    • PENICILLAMINE DISULFIDE [USP-RS]
    • D-Valine, 3,3'-dithiobis-
    • PENICILLAMINE DISULFIDE D-FORM [MI]
    • 3,3,3,',3'-tetramethyl-D-cystine
    • S,S'-Bi(D-penicillamine)
    • (2S,2'S)-3,3'-disulfanediylbis(2-amino-3-methylbutanoic acid)
    • NSC-87505
    • (2S,2'S)-3,3'-dithiobis(2-amino-3-methylbutyric acid)
    • PENICILLAMINE DISULFIDE, D-
    • Penicillamine disulfide, United States Pharmacopeia (USP) Reference Standard
    • Q98FPI4N5P
    • UNII-Q98FPI4N5P
    • SCHEMBL6501684
    • D-Penicillamine disulfide, 97%
    • 3,3'-Dithiobis(2-amino-3-methylbutyric acid)
    • DTXSID201312638
    • 3,3'-Dithiobis(2-amino-3-methylbutanoic acid)
    • (2S)-2-amino-3-[[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl]-3-methylbutanoic acid
    • 20902-45-8
    • (2S,2'S)-3,3'-dithiobis(2-amino-3-methylbutanoic acid)
    • (2S)-2-amino-3-{[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl}-3-methylbutanoic acid
    • CHEBI:61196
    • Penicillamine disulfide, European Pharmacopoeia (EP) Reference Standard
    • EINECS 244-107-2
    • Q27130878
    • G77264
    • POYPKGFSZHXASD-WDSKDSINSA-N
    • MDL: MFCD00004264
    • Inchi: 1S/C10H20N2O4S2/c1-9(2,5(11)7(13)14)17-18-10(3,4)6(12)8(15)16/h5-6H,11-12H2,1-4H3,(H,13,14)(H,15,16)/t5-,6-/m0/s1
    • InChI Key: POYPKGFSZHXASD-WDSKDSINSA-N
    • SMILES: S(C(C)(C)[C@H](C(=O)O)N)SC(C)(C)[C@H](C(=O)O)N

Computed Properties

  • Exact Mass: 296.08600
  • Monoisotopic Mass: 296.086
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 7
  • Complexity: 302
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 177A^2
  • XLogP3: -5

Experimental Properties

  • Color/Form: solid
  • Density: 1.353
  • Melting Point: 204-205?°C (lit.)
  • Boiling Point: 467°Cat760mmHg
  • Flash Point: 236.2°C
  • Refractive Index: 1.595
  • PSA: 177.24000
  • LogP: 2.14940
  • Solubility: Not determined
  • Merck: 13,7161
  • Specific Rotation: D23 +27° (c = 1.46 in 1N HCl)
  • Optical Activity: [α]25/D ?75°, c =?1 in 1 M NaOH

D-Penicillamine Disulfide Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S26; S36
  • Hazardous Material Identification: Xi
  • Risk Phrases:R36/37/38
  • Storage Condition:2-8oC

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Additional information on D-Penicillamine Disulfide

D-Penicillamine Disulfide: A Comprehensive Overview of Its Chemical Profile and Emerging Applications

The compound CAS no. 20902-45-8, chemically known as D-Penicillamine Disulfide, represents a significant molecule in the realm of pharmaceutical chemistry and biochemistry. This organosulfur compound, characterized by its disulfide bridge, has garnered considerable attention due to its versatile applications in medicine, particularly in the treatment of various neurological and autoimmune disorders. The unique structural and electronic properties of D-Penicillamine Disulfide make it a valuable candidate for further research and development, especially in the context of novel drug formulations.

Historically, penicillamine derivatives have been employed in the management of conditions such as rheumatoid arthritis and Wilson's disease. The disulfide form, D-Penicillamine Disulfide, enhances the stability and bioavailability of penicillamine, thereby improving therapeutic efficacy. Recent advancements in synthetic methodologies have enabled the production of high-purity forms of this compound, facilitating more precise pharmacological studies. The disulfide linkage not only contributes to the compound's stability but also influences its redox properties, making it a potential candidate for applications in antioxidant therapy.

In contemporary research, D-Penicillamine Disulfide is being explored for its potential role in neurodegenerative diseases. Studies indicate that its ability to cross the blood-brain barrier and exert neuroprotective effects makes it a promising therapeutic agent against conditions such as Parkinson's disease and Alzheimer's disease. The compound's sulfhydryl groups facilitate interactions with reactive oxygen species, thereby mitigating oxidative stress—a key pathological mechanism in these disorders. Furthermore, preclinical trials have demonstrated its efficacy in reducing neuroinflammation and protecting neuronal cells from apoptosis.

The chemical synthesis of CAS no. 20902-45-8 involves multi-step processes that require precise control over reaction conditions to ensure high yield and purity. Modern synthetic techniques, including catalytic hydrogenation and oxidative coupling reactions, have been optimized to produce this compound efficiently. The use of chiral catalysts has also enabled the synthesis of enantiomerically pure forms, which is crucial for pharmacological applications where stereochemistry plays a pivotal role.

From a biochemical perspective, D-Penicillamine Disulfide interacts with various biological targets, including metal ions and enzymes involved in redox signaling pathways. Its ability to bind transition metals such as copper and iron makes it a potential therapeutic agent against metalloproteinase-mediated diseases. Additionally, its interaction with glutathione S-transferases highlights its role in detoxification processes within cells. These interactions underscore the compound's multifaceted pharmacological profile.

The pharmaceutical industry is increasingly interested in developing novel formulations of D-Penicillamine Disulfide to enhance its therapeutic potential. Nanoencapsulation techniques have been employed to improve drug delivery efficiency, allowing for targeted action at affected sites while minimizing systemic side effects. Furthermore, combination therapies involving D-Penicillamine Disulfide with other bioactive molecules are being investigated to achieve synergistic effects in treating complex diseases.

Emerging research also suggests that CAS no. 20902-45-8 may have applications beyond traditional medicine. Its antioxidant properties make it a candidate for use in cosmetic formulations aimed at protecting skin from oxidative damage caused by environmental stressors such as UV radiation and pollutants. Additionally, studies are exploring its potential role in regenerative medicine, where its ability to modulate cellular signaling pathways could aid in tissue repair and wound healing.

The safety profile of D-Penicillamine Disulfide remains a critical area of investigation. While generally well-tolerated at therapeutic doses, potential side effects such as allergic reactions and gastrointestinal disturbances have been reported. Ongoing clinical trials are aimed at identifying optimal dosing regimens and monitoring long-term effects to ensure patient safety. Pharmacovigilance programs are essential to gather comprehensive data on the compound's adverse effects and interactions with other medications.

In conclusion, D-Penicillamine Disulfide, with its unique chemical properties and broad range of potential applications, stands out as a significant molecule in modern pharmaceutical research. Its role in treating neurological disorders, coupled with its antioxidant and metal-binding capabilities, positions it as a versatile therapeutic agent. Continued advancements in synthetic chemistry and drug delivery systems will further enhance its clinical utility. As research progresses, new applications for this compound are likely to emerge, solidifying its importance in the field of medicinal chemistry.

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