Cycloserine


Cycloserine
Cycloserine
Systematic (IUPAC) name
(R)-4-amino-1,2-oxazolidin-3-one
Clinical data
Trade names Seromycin
AHFS/Drugs.com monograph
Pregnancy cat. C
Legal status  ?
Pharmacokinetic data
Bioavailability ~70% to 90%
Metabolism Hepatic
Half-life 10 hrs (normal renal function)
Excretion Renal
Identifiers
CAS number 68-41-7 YesY
ATC code J04AB01
PubChem CID 6234
DrugBank APRD00894
ChemSpider 5998 YesY
UNII 95IK5KI84Z YesY
KEGG D00877 YesY
ChEBI CHEBI:40009 YesY
ChEMBL CHEMBL771 YesY
Chemical data
Formula C3H6N2O2 
Mol. mass 102.092 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Cycloserine is an antibiotic effective against Mycobacterium tuberculosis. For the treatment of tuberculosis, it is classified as a second line drug, i.e. its use is only considered if one or more first line drugs cannot be used.

Although in principle active against other bacteria as well, cycloserine is not commonly used in the treatment of infections other than tuberculosis.

Mode of action

The terminal two amino acid residues of the murein precursor lipid II consist of D-alanine, which is produced by the enzyme alanine racemase; the two residues are joined by D-alanine ligase. Both enzymes are competitively inhibited by cycloserine.[1]

Applications and side effects unrelated to antibiotic activity

It is also being trialed as an adjuvant to exposure therapy for anxiety disorders (e.g. phobias[2]), depression, obsessive-compulsive disorder and schizophrenia. It has been experimentally used for treatment of Gaucher's disease.

Recent research suggests that D-cycloserine (d-4-amino-3-isoxazolidinone) may be effective in treating chronic pain.[3]

The side effects are mainly central nervous system (CNS) manifestations, i.e. headache, irritability, depression, psychosis convulsions. Co-administration of pyridoxine can reduce the incidence of some of the CNS side effects (e.g. convulsions).

These psychotropic responses are related to D-cycloserine's action as a partial agonist of the neuronal NMDA receptor for glutamate and have been examined in implications with sensory-related fear extinction in the amygdala,[2] and extinction of cocaine seeking in the nucleus accumbens.[4]

D-cycloserine is a partial agonist at the glycine receptor, and has been shown to have cognition-enhancing properties for models of Parkinsons disease in primates.[5]

References


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Look at other dictionaries:

  • cycloserine — cycloserine. См. циклосерин. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • cycloserine — cikloserinas statusas T sritis chemija formulė Formulę žr. priede. priedas( ai) Grafinis formatas atitikmenys: angl. cycloserine rus. циклосерин ryšiai: sinonimas – 4 amino 3 izoksazolidinonas …   Chemijos terminų aiškinamasis žodynas

  • cycloserine — noun an antibiotic that is especially active against the tubercle bacillus • Hypernyms: ↑antibiotic, ↑antibiotic drug * * * “+ noun Etymology: cycl + serine : an antibiotic C3H4NO2NH2 derived from isoxazole that is especially active against the… …   Useful english dictionary

  • cycloserine — noun Date: 1952 a broad spectrum antibiotic C3H6N2O2 produced by an actinomycete (Streptomyces orchidaceus) and used especially in the treatment of tuberculosis …   New Collegiate Dictionary

  • cycloserine — cy·clo·ser·ine (sī klō sĕrʹēn) n. An antibiotic effective against a wide range of bacteria, used especially in the treatment of tuberculosis and infections of the urinary tract. * * * …   Universalium

  • cycloserine — noun an antibiotic used in the treatment of tuberculosis …   Wiktionary

  • cycloserine — An antibiotic produced by strains of Streptomyces orchidaceus or S. garyphalus with a wide spectrum of antibacterial activity. SYN: orientomycin. * * * cy·clo·ser·ine .sī klō se(ə)r .ēn, .sik lō n a broad spectrum antibiotic C3H6N2O2 produced by… …   Medical dictionary

  • cycloserine — cy·clo·serine …   English syllables

  • cycloserine — n. an antibiotic, active against a wide range of bacteria, that may be used as supporting treatment in tuberculosis. It is administered by mouth; side effects, which can be severe, include headache, dizziness, drowsiness, convulsions, and mental… …   The new mediacal dictionary

  • cycloserine enrichment — cycloserine enrichment. См. обогащение с помощью циклосерина. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.