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Cycloserine information


Cycloserine
Clinical data
Trade namesSeromycin
Other namesD-cycloserine, 4-amino-3-isoxazolidinone
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Seromycin
ATC code
  • J04AB01 (WHO)
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailability~70% to 90%
MetabolismLiver
Elimination half-life10 hrs (normal kidney function)
ExcretionKidney
Identifiers
IUPAC name
  • (R)-4-Amino-1,2-oxazolidin-3-one
CAS Number
  • 68-41-7 checkY
PubChem CID
  • 6234
DrugBank
  • DB00260 checkY
ChemSpider
  • 5998 checkY
UNII
  • 95IK5KI84Z
KEGG
  • D00877 checkY
ChEBI
  • CHEBI:40009 checkY
ChEMBL
  • ChEMBL771 checkY
NIAID ChemDB
  • 007654
CompTox Dashboard (EPA)
  • DTXSID8022870 Edit this at Wikidata
ECHA InfoCard100.000.626 Edit this at Wikidata
Chemical and physical data
FormulaC3H6N2O2
Molar mass102.093 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point155 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 checkY
  • Key:DYDCUQKUCUHJBH-UWTATZPHSA-N checkY
  (verify)

Cycloserine, sold under the brand name Seromycin, is a GABA transaminase inhibitor and an antibiotic, used to treat tuberculosis.[1][2] Specifically it is used, along with other antituberculosis medications, for active drug resistant tuberculosis.[2] It is given by mouth.[2]

Common side effects include allergic reactions, seizures, sleepiness, unsteadiness, and numbness.[2] It is not recommended in people who have kidney failure, epilepsy, depression, or are alcoholics.[2] It is unclear if use during pregnancy is safe for the baby.[2] Cycloserine is similar in structure to the amino acid D-alanine and works by interfering with the formation of the bacteria's cell wall.[2]

Cycloserine was discovered in 1954 from a type of Streptomyces.[3] It is on the World Health Organization's List of Essential Medicines.[4]

  1. ^ Polc P, Pieri L, Bonetti EP, Scherschlicht R, Moehler H, Kettler R, et al. (April 1986). "L-cycloserine: behavioural and biochemical effects after single and repeated administration to mice, rats and cats". Neuropharmacology. 25 (4). Elsevier BV: 411–418. doi:10.1016/0028-3908(86)90236-4. PMID 3012401. S2CID 462885.
  2. ^ a b c d e f g "Cycloserine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  3. ^ Gottlieb D, Shaw PD (2012). Mechanism of Action. Springer Science & Business Media. p. 41. ISBN 9783642460517. Archived from the original on 2016-12-20.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Cycloserine

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Cycloserine, sold under the brand name Seromycin, is a GABA transaminase inhibitor and an antibiotic, used to treat tuberculosis. Specifically it is used...

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Ailurophobia

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cynophobia. There are no medications designed to treat ailurophobia. D-cycloserine has been linked to facilitating better results in exposure therapy. List...

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Traumatic memories

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forgetting. D-cycloserine is a chemical which enhances (agonist) the activity of the NMDA receptors. When used in rats, D-cycloserine was shown to produce...

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Stefan Hofmann

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for anxiety disorders is extinction learning. Hofmann has shown that d-cycloserine, a partial agonist of the glutamate receptor can augment extinction learning...

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Terizidone

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(MDR-TB) in conjunction with other second-line drugs. It is a derivate of cycloserine and it is bacteriostatic. Galietti F, Giorgis GE, Oliaro A, Boaro D,...

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GABA transaminase inhibitor

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metabolize to it, such as phenelzine), ethanolamine-O-sulfate (EOS), and L-cycloserine. Certain members of this class are used as anticonvulsants. Ciesielski...

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Specific phobia

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suggesting that adjuvant use of the NMDA receptor partial agonist, d-cycloserine, with virtual reality exposure therapy may improve specific phobia symptoms...

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Glycine

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Nitric oxide

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Phenobarbital

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Ketamine

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Sideroblastic anemia

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mitochondrial membrane protein, impairs mitochondrial respiration), cycloserine, and linezolid. Ringed sideroblasts are seen in the bone marrow. On the...

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Pethidine

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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MDMA

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neurochemical recovery must be addressed. The author noted that oxytocin and D-cycloserine are potentially safer co-drugs in PTSD treatment, albeit with limited...

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Carisoprodol

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Glutamine

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Magnesium

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Zinc

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Saffron

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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NMDA receptor

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Aminocyclopropanecarboxylic acid (ACC) – synthetic glycine site partial agonist Cycloserine (D-cycloserine) – naturally occurring glycine site partial agonist found in Streptomyces...

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Social anxiety disorder

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research. It has been shown that a combination of acute dosing of d-cycloserine (DCS) with exposure therapy facilitates the effects of exposure therapy...

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Gabapentin

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dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol) Others Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol...

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Inhalational anesthetic

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ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine...

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Alanine transaminase

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Hydrazinosuccinate ALTTooltip Alanine aminotransferase β-Chloro-L-alanine L-Cycloserine Propargylglycine GDHTooltip Glutamate dehydrogenase AAOA Bithionol Chloroquine...

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Hydrazinosuccinate ALTTooltip Alanine aminotransferase β-Chloro-L-alanine L-Cycloserine Propargylglycine GDHTooltip Glutamate dehydrogenase AAOA Bithionol Chloroquine...

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