Cycloserine

Cycloserine
Clinical data
Trade names	Seromycin
Other names	D-cycloserine, 4-amino-3-isoxazolidinone
AHFS/Drugs.com	Monograph
License data	US DailyMed: Seromycin;
ATC code	J04AB01 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	~70% to 90%
Metabolism	Liver
Elimination half-life	10 hrs (normal kidney function)
Excretion	Kidney
Identifiers
	IUPAC name (R)-4-Amino-1,2-oxazolidin-3-one;
CAS Number	68-41-7 ;
PubChem CID	6234;
DrugBank	DB00260 ;
ChemSpider	5998 ;
UNII	95IK5KI84Z;
KEGG	D00877 ;
ChEBI	CHEBI:40009 ;
ChEMBL	ChEMBL771 ;
NIAID ChemDB	007654;
CompTox Dashboard (EPA)	DTXSID8022870 ;
ECHA InfoCard	100.000.626
Chemical and physical data
Formula	C3H6N2O2
Molar mass	102.093 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	155 to 156 °C (311 to 313 °F) (dec.)
	SMILES O=C1NOC[C@H]1N;
	InChI InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1 ; Key:DYDCUQKUCUHJBH-UWTATZPHSA-N ;
	(verify)

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

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

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

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