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Penicillamine information


Penicillamine
Clinical data
Trade namesCuprimine, Cuprenyl, Depen, others
Other names
  • D-penicillamine
  • (–)-penicillamine
AHFS/Drugs.comMonograph
MedlinePlusa618021
License data
  • US DailyMed: Penicillamine
Pregnancy
category
  • AU: D
Routes of
administration
By mouth (capsules)
ATC code
  • M01CC01 (WHO)
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVariable
MetabolismLiver
Elimination half-life1 hour
ExcretionKidney
Identifiers
IUPAC name
  • (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
CAS Number
  • 52-67-5 checkY
PubChem CID
  • 5852
IUPHAR/BPS
  • 7264
DrugBank
  • DB00859 checkY
ChemSpider
  • 5643 checkY
UNII
  • GNN1DV99GX
KEGG
  • D00496 checkY
ChEBI
  • CHEBI:7959 checkY
ChEMBL
  • ChEMBL1430 checkY
CompTox Dashboard (EPA)
  • DTXSID6037069 Edit this at Wikidata
ECHA InfoCard100.000.136 Edit this at Wikidata
Chemical and physical data
FormulaC5H11NO2S
Molar mass149.21 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC(C)([C@H](C(=O)O)N)S
InChI
  • InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1 checkY
  • Key:VVNCNSJFMMFHPL-VKHMYHEASA-N checkY
  (verify)

Penicillamine, sold under the brand name of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease.[1] It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, and various heavy metal poisonings.[1][2] It is taken by mouth.[2]

Penicillamine was approved for medical use in the United States in 1970.[1] It is on the World Health Organization's List of Essential Medicines.[3]

  1. ^ a b c "Penicillamine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  2. ^ a b Cite error: The named reference WHO2008 was invoked but never defined (see the help page).
  3. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.{{cite book}}: CS1 maint: location missing publisher (link)

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Penicillamine

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Penicillamine, sold under the brand name of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease. It is also used...

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Chiral drugs

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for a chiral switch. Penicillamine is a chiral drug with one chiral center and exists as a pair of enantiomers. (S)-penicillamine is the eutomer with the...

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Triethylenetetramine

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those who are intolerant to penicillamine. Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive. Trientine...

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Neutropenia

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Influenza Human Immunodeficiency Virus Propylthiouracil Levamisole Penicillamine Trimethoprim/sulfamethoxazole Clozapine Valproate Vaccination Venetoclax...

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Breast hypertrophy

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macromastia), in adult women without any obvious cause, associated with penicillamine therapy, and associated with extreme obesity. Many definitions of macromastia...

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Binding selectivity

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atoms are N, O or F as with ligands whose donor atoms are P, S or Cl. Penicillamine, which contains nitrogen and sulphur donor atoms, is used as this type...

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WHO Model List of Essential Medicines

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Calcium gluconate Methylthioninium chloride (methylene blue) Naloxone Penicillamine Prussian blue Sodium nitrite Sodium thiosulfate Complementary: Deferoxamineα...

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Nephrotoxicity

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glomerulosclerosis Gold salts therapy can cause membranous nephropathy Penicillamine Lithium salts Amphotericin B—reversible at low doses, irreversible at...

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Chelation therapy

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(DMPS) severe acute arsenic poisoning severe acute mercury poisoning Penicillamine Mainly in: copper toxicity Occasionally adjunctive therapy in: gold...

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Chorea

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used. Wilson's disease Reducing levels of copper in the body using D-penicillamine, trientine hydrochloride, tetrathiomolybdate, and other chelating agents...

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Acrodynia

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dimercaprol (British antilewisite; 2,3-dimer-capto-l-propanol) and D-penicillamine were the most popular treatment modalities. Disodium edetate (Versene)...

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Proteinuria

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Diabetes mellitus (diabetic nephropathy) Drugs (e.g. NSAIDs, nicotine, penicillamine, lithium carbonate, gold and other heavy metals, ACE inhibitors, antibiotics...

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Pulmonary fibrosis

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immunosuppressants, such as cyclophosphamide, azathioprine, methotrexate, penicillamine, and cyclosporine may be used. Colchicine has also been used with limited...

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Bullous pemphigoid

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nonsteroidal anti-inflammatory agents, DPP-4 inhibitors, captopril, penicillamine, and antibiotics. The bullae are formed by an immune reaction, initiated...

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Vitamin B6

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and treatment with certain anticonvulsants, isoniazid, cycloserine, penicillamine, and hydrocortisone negatively impact vitamin B6 status. Hemodialysis...

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Rheumatoid arthritis

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as a consequence of untreated chronic inflammation. Treatment with penicillamine or gold salts such as sodium aurothiomalate are recognized causes of...

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Mercury poisoning

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cyanide, leading to simultaneous cyanide poisoning. The drug n-acetyl penicillamine has been used to treat mercury poisoning with limited success. Quicksilver...

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Lead poisoning

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(CaNa2EDTA), dimercaprol (BAL), which are injected, and succimer and d-penicillamine, which are administered orally. Chelation therapy is used in cases of...

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Cirrhosis

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builds up in organs. This is carried out using chelation therapy such as penicillamine. When the cause is an iron overload, iron is removed using a chelation...

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Enantioselective synthesis

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effects. Drug safety: D‑penicillamine is used in chelation therapy and for the treatment of rheumatoid arthritis whereas L‑penicillamine is toxic as it inhibits...

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Mammoplasia

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agents. Other drugs that have been associated with mammoplasia include D-penicillamine, bucillamine, neothetazone, ciclosporin, indinavir, marijuana, and cimetidine...

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Hydroxychloroquine

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(Lanoxin). Hydroxychloroquine can increase plasma concentrations of penicillamine which may contribute to the development of severe side effects. It enhances...

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Dimercaprol

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acid Dimercaptosuccinic acid DMSA scan EDTA Heavy metal poisoning Penicillamine Poisoning in Children. Jaypee Brothers Publishers. 2013. p. 70. ISBN 978-93-5025-773-9...

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Copper toxicity

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antimony, cadmium, and chromium. In cases of suspected copper poisoning, penicillamine is the drug of choice, and dimercaprol, a heavy metal chelating agent...

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Glomerulonephritis

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bowel, infections such as hepatitis B and malaria, drugs including penicillamine, and connective tissue diseases such as systemic lupus erythematosus...

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