Terminology Service for NFDI4Health
JSON

D-cycloserine

Go to external page http://purl.obolibrary.org/obo/CHEBI_40009

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).

Term info

Label

D-cycloserine

Synonyms
  • (4R)-4-aminoisoxazolidin-3-one
  • D-Cycloserine
database cross reference
Subsets

3_STAR

IUPAC NAME
(4R)-4-aminoisoxazolidin-3-one [ IUPAC ]

INN
cycloserinum [ ChemIDplus ]

INN
cycloserine [ ChemIDplus ]

BRAND NAME
Seromycin [ ChemIDplus ]

INN
cicloserina [ ChemIDplus ]

INN
cycloserine [ WHO_MedNet ]

charge

0

formula

C3H6N2O2

has alternative id

CHEBI:4030

has obo namespace

chebi_ontology

has related synonym

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

id

CHEBI:40009

inchi

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

inchikey

DYDCUQKUCUHJBH-UWTATZPHSA-N

mass

102.09190

monoisotopicmass

102.04293

smiles

[H][C@@]1(N)CONC1=O