1113-41-3 Usage
Description
L-Penicillamine, also known as the L-enantiomer of penicillamine, is a white to almost white crystalline powder that is a metabolite of penicillin. It is characterized by its metal-chelating properties, which make it a versatile compound with various applications in the medical and pharmaceutical industries.
Uses
Used in Pharmaceutical Applications:
L-Penicillamine is used as a therapeutic agent for the treatment of various medical conditions, including Wilson's disease, Cystinuria, Scleroderma, and arsenic poisoning. Its metal-chelating properties allow it to bind and remove excess metals from the body, making it an essential component in the management of these diseases.
Used in Metal Chelation:
L-Penicillamine is used as a metal-chelating agent, which is crucial in the treatment of heavy metal poisoning and the removal of excess metals from the body. Its ability to bind with metals such as copper, lead, and mercury makes it a valuable tool in detoxification and chelation therapy.
Indications
Penicillamine (Cuprimine) can be used to treat acute,
severe rheumatoid arthritis, producing reductions in
joint pain, edema, and stiffness.The response to penicillamine
is usually delayed (4–12 weeks), and remissions
can last several months after withdrawal of treatment.
Radiographic evidence of this drug’s efficacy is limited;
thus, penicillamine is seldom used to treat rheumatoid
arthritis.
Mechanism of action
The mechanism of action of penicillamine is
unknown, but some evidence suggests that it may involve
the inhibition of angiogenesis, synovial fibroblast
proliferation, or transcriptional activation. Because
penicillamine can chelate copper and promote its excretion,
it is used to treat Wilson’s disease (hepatolenticular
degeneration) and has also been used in mercury
and lead intoxication.
Pharmacology
Penicillamine is readily absorbed from the GI tract
and is rapidly excreted in the urine, largely as the intact
molecule. Gradually increasing its dose minimizes side
effects, which necessitate discontinuance of penicillamine
therapy in perhaps one-third of patients. The
most common side effects are maculopapular pruritic
dermatitis, GI upset, loss of taste sensation, mild to occasionally
severe thrombocytopenia and leukopenia,and mild proteinuria, which at times may progress to
the nephritic syndrome. Discontinuance of therapy usually
results in a rapid disappearance of side effects.
Safety Profile
A poison by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx and SOx.
Purification Methods
Same as preceding entry for its enantiomer. [Beilstein 4 IV 3228.]
Check Digit Verification of cas no
The CAS Registry Mumber 1113-41-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 3 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1113-41:
(6*1)+(5*1)+(4*1)+(3*3)+(2*4)+(1*1)=33
33 % 10 = 3
So 1113-41-3 is a valid CAS Registry Number.
1113-41-3Relevant articles and documents
Enantiomeric analysis of pharmaceutical compounds by Ion/molecule reactions
Grigorean,Lebrilla
, p. 1684 - 1691 (2001)
Protonated complexes involving cyclodextrin hosts and guest compounds that are pharmacologically important are produced in the gas phase and reacted with a gaseous amine. The guest is exchanged to produce a new protonated complex with the amine. The reaction is enantioselective and is used to develop a method for determining enantiomeric excess using only mass spectrometry. The pharmaceutical compounds include DOPA, amphetamine, ephedrine, and penicillamine. The presence of more than one reacting species is observed with DOPA and penicillamine. Molecular dynamics calculations are used to understand the nature of the interactions and the possible source of the variations in the reactivities.
Determination of Absolute Rate Constants for the Reversible Hydrogen-atom Transfer between Thiyl Radicals and Alcohols or Ethers
Schoeneich, Christian,Asmus, Klaus-Dieter,Bonifacic, Marija
, p. 1923 - 1930 (2007/10/02)
Absolute rate constants have been determined for the reversible hydrogen-transfer process R. + RSH ->/. by pulse radiolysis, mainly through direct observation of the RS. radical formation kinetics in water-RH (1:1, v/v) mixtures.The thiols investigated were penicillamine and glutathione; the RH hydrogen donors were methanol, ethanol, propan-1-ol, propan-2-ol, ethylene glycol, tetrahydrofuran and 1,4-dioxane with the abstracted hydrogen being located α to the hydroxy or alkoxy function.Rate constants for the forward reaction of the above equilibrium (in radiation biology referred to as 'repair' reaction) were typically of the order of 1E7-1E8 dm3 mol-1 s-1 while hydrogen abstraction from RH by thiyl radicals (reverse process) occurred with rate constants of the order of 1E3-1E4 dm3 mol-1 s-1.This yields equilibrium constants of the order of 1E4.Based on these data, standard reduction potentials could be evaluated for the R'R''C.OH/H(1+)//R'R''CHOH, R'R''CO/H(1+)//R'R''C.(OH) and R'R''CO//R'R''C.O(1-) couples from methanol, ethanol and propan-2-ol.Effective hydrogen-atom abstraction by RS. required activation by neighbouring groups of the C-H bond to be cleaved in RH.No such process was observed for the RS. reaction with -CH3 groups, e.g. in 2-methylpropan-2-ol.Several halogenated hydrocarbons, including some anaesthetics (e.g. halothane) and Fe(CN)6(3-) have been tested with respect to their ability to disturb the (CH3)2C.OH + RSH ->/. equilibrium through an irreversible electron-transfer reaction with the reducing α-hydroxyl radical, thereby drawing the equilibrium to the left-hand side.The respective efficiencies are found to be related to the electronegativities of the electron acceptors.The results are briefly discussed in terms of their biological relevance.