Cycloserine

Cycloserine
Clinical data
Trade namesSeromycin
Other namesD-cycloserine, 4-amino-3-isoxazolidinone
AHFS/Drugs.comMonograph
License data
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~70% to 90%
MetabolismLiver
Elimination half-life10 hrs (normal kidney function)
ExcretionKidney
Identifiers
  • (R)-4-Amino-1,2-oxazolidin-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.626 Edit this at Wikidata
Chemical and physical data
FormulaC3H6N2O2
Molar mass102.093 g·mol−1
3D model (JSmol)
Melting point155 to 156 °C (311 to 313 °F) (dec.)
  • O=C1NOC[C@H]1N
  • InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1 checkY
  • Key:DYDCUQKUCUHJBH-UWTATZPHSA-N checkY
  (verify)

Cycloserine, sold under the brand name Seromycin, is a GABA transaminase inhibitor and an antibiotic, used to treat tuberculosis.[1][2] Specifically it is used, along with other antituberculosis medications, for active drug resistant tuberculosis.[2] It is given by mouth.[2]

Common side effects include allergic reactions, seizures, sleepiness, unsteadiness, and numbness.[2] It is not recommended in people who have kidney failure, epilepsy, depression, or are alcoholics.[2] It is unclear if use during pregnancy is safe for the baby.[2] Cycloserine is similar in structure to the amino acid D-alanine and works by interfering with the formation of the bacteria's cell wall.[2]

Cycloserine was discovered in 1954 from a type of Streptomyces.[3] It is on the World Health Organization's List of Essential Medicines.[4]

  1. ^ Polc P, Pieri L, Bonetti EP, Scherschlicht R, Moehler H, Kettler R, et al. (April 1986). "L-cycloserine: behavioural and biochemical effects after single and repeated administration to mice, rats and cats". Neuropharmacology. 25 (4). Elsevier BV: 411–418. doi:10.1016/0028-3908(86)90236-4. PMID 3012401. S2CID 462885.
  2. ^ a b c d e f g "Cycloserine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  3. ^ Gottlieb D, Shaw PD (2012). Mechanism of Action. Springer Science & Business Media. p. 41. ISBN 9783642460517. Archived from the original on 2016-12-20.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.