cycloserine

Also known as PA-94, (+)-4-Amino-3-isoxazolidinone, alpha-Cycloserine, Cicloserina, PA 94, D-(+)-Cycloserine, (R)-4-AMINO-isoxazolidin-3-one, (+)-Cycloserine

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.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 460111047
Drug.image: Cycloserine.svg
Drug.image_class: skin-invert-image
Drug.width: 150px
Drug.image2: Cycloserine ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.width2: 125px
Drug.tradename: Seromycin
Drug.DailyMedID: Seromycin
Drug.routes_of_administration: Oral
Drug.class: Antibiotic; Alanine racemase inhibitor; D-Alanine–D-alanine ligase inhibitor; NMDA receptor partial agonist; GABA-T inhibitor
Drug.ATC_prefix: J04
Drug.ATC_suffix: AB01
Drug.legal_US: Rx-only
Drug.bioavailability: ~70% to 90%
Drug.metabolism: Liver
Drug.elimination_half life: 10 hours (normal kidney function)

via Wikipedia infobox

Chemical data

Formula: C3H6N2O2
Molecular weight: 102.09 g/mol
IUPAC name: (4R)-4-amino-1,2-oxazolidin-3-one
SMILES: C1[C@H](C(=O)NO1)N
InChIKey: DYDCUQKUCUHJBH-UWTATZPHSA-N
XLogP: -1.5
Polar surface area: 64.4 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

3,834 papers

Cycloserine.Tuberculosis (Edinburgh, Scotland) · 2008
Cycloserine.Antibiotics and chemotherapy · 1971
D-cycloserine for Alzheimer's disease.The Cochrane database of systematic reviews · 2002
D-cycloserine augmentation of behavioral therapy for the treatment of anxiety disorders: a meta-analysis.The Journal of clinical psychiatry · 2012
Critical parameters for D-cycloserine enhancement of cognitive-behaviorial therapy for obsessive-compulsive disorder.The American journal of psychiatry · 2008

via PubMed

Wikidata facts

Mass: 102.043

Show 7 more facts

chemical formula: C₃H₆N₂O₂
Commons category: Cycloserine
defined daily dose: 0.75
isomeric SMILES: C1[C@H](C(=O)NO1)N
canonical SMILES: C1C(C(=O)NO1)N
World Health Organisation international non-proprietary name: cycloserine
stylized name: cycloSERINE

Sources (8)

via Wikidata · CC0

~7 min read

Article

15 sections

Contents

Medical uses
Tuberculosis
Pharmacology
Mechanism of action
Chemistry
Chemical properties
Synthesis
History
Society and culture
Economics
Research
Psychiatric disorders
Possible hallucinogenic effects
References
Further reading

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.