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

• Beilstein:80798
• CAS:68-41-7
• DrugBank:DB00260
• Drug_Central:759
• HMDB:HMDB0014405
• KEGG:D00877
• LINCS:LSM-5932
• LIPID_MAPS_instance:LMPK14000007
• MetaCyc:CPD-2482
• PDBeChem:4AX
• PMID:12076471
• PMID:17707326
• PMID:18316423
• PMID:18486041
• PMID:18930757
• PMID:22234379
• PMID:22368237
• PMID:22632472
• PMID:22892161
• PMID:23174090
• PMID:23416058
• PMID:23438729
• PMID:23523746
• PMID:23542909
• PMID:23656850
• PMID:23685206
• PMID:4555420
• PMID:5006234
• Patent:US2772280
• Patent:US2840565
• Reaxys:80798
• Wikipedia:Cycloserine

Ontology

ChEBI  ( EBI )

Resources

CTD