Difference between revisions of "Cycloserine"

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Revision as of 14:06, 6 July 2010

Not to be confused with Cyclosarin.
Cycloserine
File:Cycloserine.svg
Systematic (IUPAC) name
(R)-4-amino-1,2-oxazolidin-3-one
Clinical data
Pregnancy
category
  • C
Pharmacokinetic data
Bioavailability ~70% to 90%
Metabolism Hepatic
Identifiers
CAS Number 68-41-7
ATC code J04AB01 (WHO)
PubChem CID 6234
DrugBank APRD00894
ChemSpider 5998
Chemical data
Formula C3H6N2O2
Molar mass 102.092 g/mol[[Script error: No such module "String".]]
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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-isoxazolidone) 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]

References

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Nucleic acid inhibitor
ASA
Protein synthesis inhibitor
Cell envelope antibiotic
Alanine analogue: Cycloserine#
Other/unknown

M: BAC

drug(J1p, w, n, m, vacc)

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) · DADAL/AR inhibitors (Cycloserine) · bactoprenol inhibitors (Bacitracin)
Glycopeptide
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin
β-lactams/
(inhibit PBP
cross-links)
Combinations
Other

M: BAC

drug(J1p, w, n, m, vacc)

Amino acids
Endocannabinoids
Gasotransmitters
Monoamines
Purines

Adenosine · ADP · AMP · ATP

Trace amines
Others
de:Cycloserin

it:Cicloserina pl:Cykloseryna pt:Oxamicina ru:Циклосерин

sr:Cikloserin
  1. ↑ "Cell Envelope.1995". Retrieved 2008-11-08. 
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  3. ↑ "Newly Identified Drug Relieves Suffering". Science Daily. 2007-06-05. Retrieved 2008-07-15. 
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