C6880

D-Cycloserine

• Synonym(s): (R)-4-Amino-3-isoxazolidone, 4-Amino-3-isoxazolidinone
• Empirical Formula (Hill Notation): C₃H₆N₂O₂
• CAS Number: 68-41-7
• Molecular Weight: 102.09
• UNSPSC Code: 12352209
• NACRES: NA.32
• PubChem Substance ID: 24892907
• EC Number: 200-688-4
• Beilstein/REAXYS Number: 80798
• MDL number: MFCD00005353

Properties

• form: powder
• Quality Segment: 200
• 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
• 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

Biochem/physiol Actions

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.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)