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Penicillamine is a pharmaceutical of the chelator
Chelation therapy

Chelation therapy is the administration of chelations to remove heavy metals from the body. For the most common forms of heavy metal intoxication?those involving lead, arsenic or Mercury ?the standard of care in the USA dictates the use of dimercaptosuccinic acid ....
 class. It is sold under the trade names of Cuprimine and Depen. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine
Pyridoxine

Pyridoxine is one of the compounds that can be called vitamin B6, along with Pyridoxal and Pyridoxamine. It differs from pyridoxamine by the substituent at the '4' position....
). It is a metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
 of penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
, although it has no antibiotic
Antibiotic

In common usage, an antibiotic is a substance or compound that kills or inhibits the growth of bacteria. Antibiotics belong to the group of antimicrobial compounds used to treat infections caused by microorganisms, including fungus and protozoa....
 properties.

cillamine is used as a form of immunosuppression
Immunosuppression

Immunosuppression involves an act that reduces the activation or efficacy of the immune system. Some portions of the immune system itself have immuno-suppressive effects on other parts of the immune system, and immunosuppression may occur as an adverse reaction to treatment of other conditions....
 to treat rheumatoid arthritis
Rheumatoid arthritis

Rheumatoid arthritis is a chronic, systemic disease inflammation that may affect many tissues and organs, but principally attacks the joints producing a inflammatory synovitis that often progresses to destruction of the articular cartilage and ankylosis of the joints....
. It works by reducing numbers of T-lymphocyte
T cell

T cells belong to a group of white blood cells known as lymphocytes, and play a central role in cell-mediated immunity. They can be distinguished from other lymphocyte types, such as B cells and natural killer cells by the presence of a special receptor on their cell surface called T cell receptors ....
s, inhibiting macrophage
Macrophage

Macrophages are white blood cells within tissues, produced by the division of monocytes. Human macrophages are about 21 micrometres in diameter....
 function, decreasing IL-1
IL-1

IL-1 may refer to:* Interleukin 1, a protein* Illinois' 1st congressional district* Illinois Route 1* Building 1 of Infinite Loop , the Headquarters of Apple Inc....
, decreasing rheumatoid factor
Rheumatoid factor

Rheumatoid factor is an autoantibody most relevant in rheumatoid arthritis. It is an antibody against the Fc portion of IgG, which is itself an antibody....
, and preventing collagen
Collagen

Collagen is the main protein of connective tissue in animals and the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content....
 from cross-linking.

Penicillamine is also used for treatment of scleroderma
Scleroderma

Systemic scleroderma is a systemic connective tissue disease.It is also known as "systemic Sclerosis "....
.

It is used as a chelating agent:

John Walshe (1956) first described the use of penicillamine in Wilson's disease.






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Penicillamine is a pharmaceutical of the chelator
Chelation therapy

Chelation therapy is the administration of chelations to remove heavy metals from the body. For the most common forms of heavy metal intoxication?those involving lead, arsenic or Mercury ?the standard of care in the USA dictates the use of dimercaptosuccinic acid ....
 class. It is sold under the trade names of Cuprimine and Depen. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine
Pyridoxine

Pyridoxine is one of the compounds that can be called vitamin B6, along with Pyridoxal and Pyridoxamine. It differs from pyridoxamine by the substituent at the '4' position....
). It is a metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
 of penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
, although it has no antibiotic
Antibiotic

In common usage, an antibiotic is a substance or compound that kills or inhibits the growth of bacteria. Antibiotics belong to the group of antimicrobial compounds used to treat infections caused by microorganisms, including fungus and protozoa....
 properties.

Uses

Penicillamine is used as a form of immunosuppression
Immunosuppression

Immunosuppression involves an act that reduces the activation or efficacy of the immune system. Some portions of the immune system itself have immuno-suppressive effects on other parts of the immune system, and immunosuppression may occur as an adverse reaction to treatment of other conditions....
 to treat rheumatoid arthritis
Rheumatoid arthritis

Rheumatoid arthritis is a chronic, systemic disease inflammation that may affect many tissues and organs, but principally attacks the joints producing a inflammatory synovitis that often progresses to destruction of the articular cartilage and ankylosis of the joints....
. It works by reducing numbers of T-lymphocyte
T cell

T cells belong to a group of white blood cells known as lymphocytes, and play a central role in cell-mediated immunity. They can be distinguished from other lymphocyte types, such as B cells and natural killer cells by the presence of a special receptor on their cell surface called T cell receptors ....
s, inhibiting macrophage
Macrophage

Macrophages are white blood cells within tissues, produced by the division of monocytes. Human macrophages are about 21 micrometres in diameter....
 function, decreasing IL-1
IL-1

IL-1 may refer to:* Interleukin 1, a protein* Illinois' 1st congressional district* Illinois Route 1* Building 1 of Infinite Loop , the Headquarters of Apple Inc....
, decreasing rheumatoid factor
Rheumatoid factor

Rheumatoid factor is an autoantibody most relevant in rheumatoid arthritis. It is an antibody against the Fc portion of IgG, which is itself an antibody....
, and preventing collagen
Collagen

Collagen is the main protein of connective tissue in animals and the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content....
 from cross-linking.

Penicillamine is also used for treatment of scleroderma
Scleroderma

Systemic scleroderma is a systemic connective tissue disease.It is also known as "systemic Sclerosis "....
.

It is used as a chelating agent:
  • In Wilson's disease
    Wilson's disease

    Wilson's disease or hepatolenticular degeneration is an autosomal recessive genetic disorder in which copper accumulates in biological tissue; this manifests as neurology or psychiatry symptoms and liver disease....
    , a rare genetic disorder of copper
    Copper

    Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
     metabolism, penicillamine treatment relies on its binding to accumulated copper and elimination through urine
    Urine

    Urine is a liquid waste product of the body secreted by the kidneys by a process of filtration from blood called urination and excreted through the urethra....
    .
  • In cystinuria
    Cystinuria

    Cystinuria is an inherited autosome dominance metabolic disorder that is characterized by the formation of cystine stones in the kidneys, ureter, and Urinary bladder....
    , a hereditary disorder featuring formation of cystine
    Cystine

    Cystine is the amino acid dimer formed when a pair of cysteine molecules are joined by a disulfide bond. It is described by the formula 2....
     stones, penicillamine binds with cysteine
    Cysteine

    Cysteine is an a-amino acid with the chemical formula HO2CCHCH2SH. It is a non-essential amino acid, which means that humans can synthesize it....
     to to yield a mixed disulfide
    Disulfide

    In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. The disulfide anion is S22-....
     which is more soluble than cystine.
  • Penicillamine has been used to treat mercury poisoning.


History

Dr. John Walshe (1956) first described the use of penicillamine in Wilson's disease. He had discovered the compound in the urine of patients (including himself) who had taken penicillin
Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They are Beta-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms....
, and experimentally confirmed that it increased urinary copper excretion by chelation
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
. He had initial difficulty convincing several world experts of the time (Drs Denny Brown and Cumings) of its efficacy, as they held that Wilson's disease was not primarily a problem of copper homeostasis but of amino acid metabolism, and that dimercaprol
Dimercaprol

Dimercaprol or British anti-Lewisite , is a compound developed by British biochemists at Oxford University during World War II. It was developed secretly as an antidote for Lewisite, the now-obsolete arsenic-based chemical warfare agent....
 should be used as a chelator. Later studies confirmed both the copper-centered theory and the efficacy of D-penicillamine. Walshe also pioneered other chelators in Wilson's such as triethylene tetramine
Triethylene tetramine

Triethylenetetramine, abbreviated TETA and trien, is an organic compound with the formula [CH2NHCH2CH2NH2]2....
 2HCl and tetrathiomolybdate.

External links

  • - Medlineplus.org
  • - Medicinenet.com