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Key Documents

C6880

Sigma-Aldrich

D-Cycloserine

Synonym(s):

(R)-4-Amino-3-isoxazolidone, 4-Amino-3-isoxazolidinone

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80798
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

form

powder

Quality Level

mp

147 °C (dec.) (lit.)

antibiotic activity spectrum

Gram-negative bacteria
mycobacteria

mode of action

cell wall synthesis | interferes

storage temp.

−20°C

SMILES string

N[C@@H]1CONC1=O

InChI

1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

InChI key

DYDCUQKUCUHJBH-UWTATZPHSA-N

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General description

Chemical structure: amino acid derivatives

Application

D-Cycloserine (DCS) has been used:
  • to study its effect on partner preference in Prairie Voles
  • to study its effect on grooming behaviour of rats
  • to determine its minimum inhibitory concentration (MIC) on 48 multidrug resistant tuberculosis (MDR-TB) isolates using the broth microdilution method
  • to study its effect on mouse model of autism, using behavioural assays

Biochem/physiol Actions

D-cycloserine (DCS) was initially known as a tuberculostatic agent. It acts as a glutamatergic partial N-methyl-D-aspartate (NMDA) agonist. It binds at the glycine-binding site of the NMDA receptor and enable the opening of the NMDA channel. DCS has a an ability to improve various forms of learning and memory hence, this drug might be effective for improving social memory and cognition. DCS can be used as a potential therapeutic for psychiatric disorders such as phobias, social anxiety, obsessive-compulsive disorder, and posttraumatic stress disorder.
Mode of Action: Inhibits cell wall biosynthesis (D-Ala peptide bond formation). Also prevents conversion of D-Ala to L-Ala. Bacteriostatic.
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
Mode of Resistance: D-Ala transport interference.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hypothesis-driven investigations of diverse pharmacological targets in two mouse models of autism
Rhine MA, et al.
Autism Research : Official Journal of the International Society for Autism Research, 147(1571), 3-3 (2019)
Determination of minimum inhibitory concentration of cycloserine in multidrug resistant Mycobacterium tuberculosis isolates
Singh R
Jordan journal of biological sciences, 147(1571), 1-7 (2014)
D-cycloserine augmented exposure therapy for obsessive-compulsive disorder
Kushner MG, et al.
Biological Psychiatry, 62(8), 835-838 (2007)
Consolidation of human motor cortical neuroplasticity by D-cycloserine
Nitsche MA, et al.
Neuropsychopharmacology, 29(8), 1573-1573 (2004)
D-cycloserine facilitates socially reinforced learning in an animal model relevant to autism spectrum disorders
Modi ME and Young LJ
Biological Psychiatry, 70(3), 298-304 (2011)

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