D-cycloserine

Term ID

CHEBI:40009

Synonyms

• (+)-4-amino-3-isoxazolidinone
• (+)-cycloserine
• (4R)-4-aminoisoxazolidin-3-one
• (R)-4-AMINO-ISOXAZOLIDIN-3-ONE
• alpha-Cycloserine
• cicloserina
• cyclo-D-serine
• cycloserine
• cycloserinum
• D-(+)-cycloserine
• D-4-amino-3-isoxazolidinone
• D-4-amino-3-isoxazolidone
• D-Cycloserine
• DCS
• orientomycin
• PA 94
• PA-94
• Ro-1-9213
• Seromycin

Definition

A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine—D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).

References

• cas:68-41-7
• drugbank:DB00260
• drugcentral:759
• hmdb:HMDB0014405
• kegg.drug:D00877
• lincs.smallmolecule:LSM-5932
• lipidmaps:LMPK14000007
• metacyc.compound:CPD-2482
• patent:US2772280
• patent:US2840565
• pdb-ccd:4AX
• pubmed:12076471
• pubmed:17707326
• pubmed:18316423
• pubmed:18486041
• pubmed:18930757
• pubmed:22234379
• pubmed:22368237
• pubmed:22632472
• pubmed:22892161
• pubmed:23174090
• pubmed:23416058
• pubmed:23438729
• pubmed:23523746
• pubmed:23542909
• pubmed:23656850
• pubmed:23685206
• pubmed:4555420
• pubmed:5006234
• reaxys:80798
• wikipedia.en:Cycloserine

Ontology

ChEBI  ( EBI )

Resources

CTD