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C6880

D-Cycloserine

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C3H6N2O2
Número CAS:
68-41-7
Peso molecular:
102.09
UNSPSC Code:
12352209
NACRES:
NA.32
PubChem Substance ID:
24892907
EC Number:
200-688-4
Beilstein/REAXYS Number:
80798
MDL number:
MFCD00005353
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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)

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.

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Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number

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