Structure via PubChem · Public domain (PubChem)
D-penicillamine
Sign in to saveAlso known as D-(-)-penicillamine, 3-mercapto-D-valine, D-beta,beta-dimethylcysteine, (-)-penicillamine, (S)-3,3-dimethylcysteine, PA, D-β,β-dimethylcysteine, (S)-2-amino-3-mercapto-3-methylbutanoic acid
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 for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, and various heavy metal poisonings. It is taken by mouth.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 456485077
- Drug.image
- Penicillamine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150
- Drug.tradename
- Cuprimine, Cuprenyl, Depen, others
- Drug.synonyms
- , 3-mercapto-L-valine, 3-mercaptovaline
- Drug.MedlinePlus
- a618021
- Drug.DailyMedID
- Penicillamine
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth (capsules)
- Drug.ATC_prefix
- M01
- Drug.ATC_suffix
- CC01
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- Variable
- Drug.metabolism
- Liver
- Drug.elimination_half life
- 1 hour
via Wikipedia infobox
Chemical data
- Formula
- C5H11NO2S
- Molecular weight
- 149.21 g/mol
- IUPAC name
- (2S)-2-azaniumyl-3-methyl-3-sulfanylbutanoate
- SMILES
- CC(C)([C@H](C(=O)[O-])[NH3+])S
- InChIKey
- VVNCNSJFMMFHPL-VKHMYHEASA-N
- XLogP
- -1.1
- Polar surface area
- 68.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
12,349 papers- D-penicillamine chemical quality.Proceedings of the Royal Society of Medicine · 1977
- D-Penicillamine--production and properties.Angewandte Chemie (International ed. in English) · 1975
- D-penicillamine.Indian pediatrics · 1991
- The metabolism and pharmacology of D-penicillamine in man.The Journal of rheumatology. Supplement · 1981
- D-penicillamine pharmacokinetics and pharmacodynamics in man.Pharmacology & therapeutics · 1989
via PubMed
Wikidata facts
- Mass
- 149.051
- Has use
- medication
Show 11 more facts
- found in taxon
- Caenorhabditis elegans
- chemical formula
- C₅H₁₁NO₂S
- route of administration
- oral administration
- medical condition treated
- Wilson disease
- defined daily dose
- 0.5
- canonical SMILES
- CC(C)(C(C(=O)O)N)S
- World Health Organisation international non-proprietary name
- penicillamine
- isomeric SMILES
- CC(C)(S)[C@@H](N)C(O)=O
- NCI Thesaurus ID
- C729
- stylized name
- penicillAMINE
- Commons category
- Penicillamine
via Wikidata · CC0
~5 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Adverse effects
- Chemistry
- History
- References
- External links
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 for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, and various heavy metal poisonings. It is taken by mouth.
Penicillamine was approved for medical use in the United States in 1970. It is on the World Health Organization's List of Essential Medicines.
Excerpted from Wikipedia’s “D-penicillamine” article, available under the CC BY-SA 4.0 licence.