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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00859
rdf:type
n9:Drug
n9:description
3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. [PubChem]
n9:dosage
n19:271B4F38-363D-11E5-9242-09173F13E4C5 n19:271B4F39-363D-11E5-9242-09173F13E4C5
n9:generalReferences
# WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/13362281 # Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12889074 # Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15495127 # Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10796440 # Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9117147
n9:group
approved
n9:halfLife
1 hour
n9:indication
For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.
n9:manufacturer
n20:271B4F33-363D-11E5-9242-09173F13E4C5 n20:271B4F32-363D-11E5-9242-09173F13E4C5
owl:sameAs
n13:DB00859 n23:DB00859
dcterms:title
Penicillamine
adms:identifier
n4:C07418 n5:D00496 n8:DB00859 n10:0037-4401-01 n11:PA450840 n15:50868 n16:Penicillamine
n9:mechanismOfAction
Penicillamine is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cystine and is excreted readily. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.
n9:packager
n20:271B4F31-363D-11E5-9242-09173F13E4C5 n20:271B4F2F-363D-11E5-9242-09173F13E4C5 n20:271B4F30-363D-11E5-9242-09173F13E4C5 n20:271B4F2D-363D-11E5-9242-09173F13E4C5 n20:271B4F2E-363D-11E5-9242-09173F13E4C5 n20:271B4F2B-363D-11E5-9242-09173F13E4C5 n20:271B4F2C-363D-11E5-9242-09173F13E4C5
n9:routeOfElimination
Excretion is mainly renal, mainly as disulfides.
n9:synonym
DL-3-Mercaptovaline beta-Mercaptovaline DL-beta-Mercaptovaline (+-)-Penicillamine 3,3-Dimethylcysteine Penicillamina 2-amino-3-Mercapto-3-methylbutyric acid D,L-Penicillamine Pénicillamine Penicilamina β-Mercaptovaline Penicillaminum
n9:foodInteraction
Food reduces availability, take on an empty stomach. Drink liberally.
n9:proteinBinding
>80% (bound to plasma proteins)
n9:synthesisReference
Manfred Klaus Joachim Bock, deceased, "Method of producing penicillamine." U.S. Patent US3968154, issued November, 1960.
n21:hasConcept
n22:M0016122
foaf:page
n7:penicillamine.html n17:penicillamine.htm
n9:IUPAC-Name
n14:271B4F3E-363D-11E5-9242-09173F13E4C5
n9:InChI
n14:271B4F44-363D-11E5-9242-09173F13E4C5
n9:Molecular-Formula
n14:271B4F43-363D-11E5-9242-09173F13E4C5
n9:Molecular-Weight
n14:271B4F40-363D-11E5-9242-09173F13E4C5
n9:Monoisotopic-Weight
n14:271B4F41-363D-11E5-9242-09173F13E4C5
n9:SMILES
n14:271B4F42-363D-11E5-9242-09173F13E4C5
n9:Water-Solubility
n14:271B4F54-363D-11E5-9242-09173F13E4C5 n14:271B4F3C-363D-11E5-9242-09173F13E4C5
n9:logP
n14:271B4F3D-363D-11E5-9242-09173F13E4C5 n14:271B4F56-363D-11E5-9242-09173F13E4C5 n14:271B4F3A-363D-11E5-9242-09173F13E4C5
n9:logS
n14:271B4F57-363D-11E5-9242-09173F13E4C5 n14:271B4F3B-363D-11E5-9242-09173F13E4C5
n9:pKa
n14:271B4F58-363D-11E5-9242-09173F13E4C5
n24:hasATCCode
n25:M01CC01
n9:H-Bond-Acceptor-Count
n14:271B4F4A-363D-11E5-9242-09173F13E4C5
n9:H-Bond-Donor-Count
n14:271B4F4B-363D-11E5-9242-09173F13E4C5
n9:InChIKey
n14:271B4F45-363D-11E5-9242-09173F13E4C5
n9:Polar-Surface-Area--PSA-
n14:271B4F46-363D-11E5-9242-09173F13E4C5
n9:Polarizability
n14:271B4F48-363D-11E5-9242-09173F13E4C5
n9:Refractivity
n14:271B4F47-363D-11E5-9242-09173F13E4C5
n9:Rotatable-Bond-Count
n14:271B4F49-363D-11E5-9242-09173F13E4C5
n9:absorption
rapidly but incompletely
n9:affectedOrganism
Humans and other mammals
n9:casRegistryNumber
52-67-5
n9:category
n9:containedIn
n18:271B4F35-363D-11E5-9242-09173F13E4C5 n18:271B4F36-363D-11E5-9242-09173F13E4C5 n18:271B4F34-363D-11E5-9242-09173F13E4C5 n18:271B4F37-363D-11E5-9242-09173F13E4C5
n9:Bioavailability
n14:271B4F50-363D-11E5-9242-09173F13E4C5
n9:Ghose-Filter
n14:271B4F52-363D-11E5-9242-09173F13E4C5
n9:MDDR-Like-Rule
n14:271B4F53-363D-11E5-9242-09173F13E4C5
n9:Melting-Point
n14:271B4F55-363D-11E5-9242-09173F13E4C5
n9:Number-of-Rings
n14:271B4F4F-363D-11E5-9242-09173F13E4C5
n9:Physiological-Charge
n14:271B4F4E-363D-11E5-9242-09173F13E4C5
n9:Rule-of-Five
n14:271B4F51-363D-11E5-9242-09173F13E4C5
n9:Traditional-IUPAC-Name
n14:271B4F3F-363D-11E5-9242-09173F13E4C5
n9:pKa--strongest-acidic-
n14:271B4F4C-363D-11E5-9242-09173F13E4C5
n9:pKa--strongest-basic-
n14:271B4F4D-363D-11E5-9242-09173F13E4C5