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Cycloserine

Cycloserine
Cycloserine.svg
Cycloserine ball-and-stick model.png
Clinical data
Trade names Seromycin
AHFS/Drugs.com Monograph
License data
Pregnancy
category
  • C
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ~70% to 90%
Metabolism liver
Biological half-life 10 hrs (normal kidney function)
Excretion kidney
Identifiers
Synonyms 4-amino-3-isoxazolidinone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
ECHA InfoCard 100.000.626
Chemical and physical data
Formula C3H6N2O2
Molar mass 102.092 g/mol
3D model (Jmol)
  

Cycloserine, sold under the brand name Seromycin, is 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 29.7 to 51.30 USD per month. In the United States in 2015 the cost was increased to 3,150 USD a month.

For the treatment of tuberculosis, cycloserine is classified as a second-line drug, i.e. its use is only considered if one or more first-line drugs cannot be used. Hence, cycloserine is restricted for use only against multiple drug-resistant and extensively drug-resistant strains of M. tuberculosis. Another reason for limited use of this drug is the neurological side effects it causes, since it is able to penetrate into the central nervous system (CNS) and cause headaches, drowsiness, depression, dizziness, vertigo, confusion, paresthesias, dysarthria, hyperirritability, psychosis, convulsions, and shaking (tremors). Overdose of cycloserine may result in paresis, seizures, and coma, while alcohol consumption may increase the risk of seizures. Coadministration of pyridoxine can reduce the incidence of some of these CNS side effects (e.g. convulsions) caused by cycloserine.


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