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C6880 Sigma-Aldrich

D-Cycloserine

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

  • CAS Number 68-41-7

  • Empirical Formula (Hill Notation) C3H6N2O2

  • Molecular Weight 102.09

  •  Beilstein/REAXYS Number 80798

  •  EC Number 200-688-4

  •  MDL number MFCD00005353

  •  PubChem Substance ID 24892907

  •  NACRES NA.32

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Properties

Related Categories A - K, Amino Acid Derivatives, Antibacterial, Antibiotics, Antibiotics A to Z,
Quality Level   200
form   powder
mp   147 °C (dec.) (lit.)
Mode of action   cell wall synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  mycobacteria
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
Gene Information   human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907)
mouse ... GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168)
rat ... GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)

Description

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

Packaging

1, 5 g in poly bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
NY2975000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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06693 Timestrip Plus -20 °C

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