Discuss This Drug

D-cycloserine

CHEBI:CHEBI_40009

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).

Chemical Information

Molecular Formula
C3H6N2O2
Molecular Mass
102.09190
Charge
0
SMILES
[H][C@@]1(N)CONC1=O
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

Alternative Names

  • cycloserine
  • (+)-4-amino-3-isoxazolidinone
  • (+)-cycloserine
  • (4R)-4-aminoisoxazolidin-3-one
  • (R)-4-AMINO-ISOXAZOLIDIN-3-ONE
  • alpha-Cycloserine
  • cicloserina
  • cyclo-D-serine
  • 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

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
3007
oboInOwl#hasDbXref
Wikipedia:Cycloserine
core#notation
CHEBI:40009

Additional References

Wikipedia:Cycloserine

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Additional Attributes

oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
3007
oboInOwl#hasDbXref
Wikipedia:Cycloserine
oboInOwl#id
CHEBI:40009
core#notation
CHEBI:40009
oboInOwl#hasAlternativeId
CHEBI:4030
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_25212
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#is_tautomer_of
http://purl.obolibrary.org/obo/CHEBI_74159
chebi#is_enantiomer_of
http://purl.obolibrary.org/obo/CHEBI_75592
chebi#is_conjugate_base_of
http://purl.obolibrary.org/obo/CHEBI_75929
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_10587
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_75929
owl#annotatedSource
t214543
owl#someValuesFrom
t691132