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Structure via PubChem · Public domain (PubChem)
Bucillamine
Sign in to saveBucillamine is an antirheumatic agent developed from tiopronin. Activity is mediated by the two thiol groups that the molecule contains. Research done in USA showed positive transplant preservation properties. Bucillamine is currently being investigated for COVID-19 drug repurposing.
Chemical data
- Formula
- C7H13NO3S2
- Molecular weight
- 223.3 g/mol
- IUPAC name
- (2R)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid
- SMILES
- CC(C)(C(=O)N[C@@H](CS)C(=O)O)S
- InChIKey
- VUAFHZCUKUDDBC-BYPYZUCNSA-N
- XLogP
- 0.4
- Polar surface area
- 68.4 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- rheumatoid arthritis, gout, rheumatic disease, COVID-19
via ChEMBL · EBI
Research
275 papers- Bucillamine: a potent thiol donor with multiple clinical applications.Cardiovascular drug reviews · 2003
- Bucillamine-induced yellow nail syndrome.Journal of general and family medicine · 2017
- Bucillamine-induced gigantomastia with galactorrhea and hyperprolactinaemia.Modern rheumatology case reports · 2020
- Bucillamine-induced interstitial pneumonitis.Journal of general and family medicine · 2018
- Bucillamine-induced toxic epidermal necrolysis and fixed drug eruption.The Journal of dermatology · 2005
via PubMed
Wikidata facts
- Subclass of
- carboxylic acid
- Mass
- 223.033685276
Show 5 more facts
- subject has role
- antioxidant
- canonical SMILES
- CC(C)(C(=O)NC(CS)C(=O)O)S
- chemical formula
- C₇H₁₃NO₃S₂
- Commons category
- Bucillamine
- isomeric SMILES
- CC(C)(C(=O)N[C@@H](CS)C(=O)O)S
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
1 sectionsContents
- References
Bucillamine is an antirheumatic agent developed from tiopronin. Activity is mediated by the two thiol groups that the molecule contains. Research done in USA showed positive transplant preservation properties. Bucillamine is currently being investigated for COVID-19 drug repurposing.
Bucillamine has a well-known safety profile and is prescribed in the treatment of rheumatoid arthritis in Japan and South Korea for over 30 years. It is a cysteine derivative with 2 thiol groups that is 16-fold more potent than acetylcysteine (NAC) as a thiol donor in vivo, giving it vastly superior function in restoring glutathione and therefore greater potential to prevent acute lung injury during influenza infection. Bucillamine has also been shown to prevent oxidative and reperfusion injury in heart and liver tissues.
Excerpted from Wikipedia’s “Bucillamine” article, available under the CC BY-SA 4.0 licence.