C3909

D-Cycloserine

synthetic

• 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
• Beilstein/REAXYS Number: 80798
• EC Number: 200-688-4
• MDL number: MFCD00005353
• UNSPSC Code: 12352209
• PubChem Substance ID: 24277962
• NACRES: NA.28

Properties

• biological source: synthetic
• form: powder
• mp: 147 °C (dec.) (lit.)
• solubility: water: 50 mg/mL, clear, colorless to light yellow
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive 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

Description

General description

Chemical structure: amino acid derivatives

Application

D-cycloserine has been used to inhibit serine hydroxymethyltransferase.[1]

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Safety Information

• 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)