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C3909

Sigma-Aldrich

D-Cycloserine

synthetic

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C3H6N2O2
Número de CAS:
68-41-7
Peso molecular:
102.09
Beilstein/REAXYS Number:
80798
EC Number:
200-688-4
MDL number:
MFCD00005353
UNSPSC Code:
12352209
PubChem Substance ID:
24277962
NACRES:
NA.28

biological source

synthetic

Quality Level

200

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

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)

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General description

Chemical structure: amino acid derivatives

Application

D-cycloserine has been used to inhibit serine hydroxymethyltransferase.

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.

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sun L, et al.
PLoS ONE, 9(3), e93405-e93405 (2014)
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Learning & memory (Cold Spring Harbor, N.Y.), 11(5), 510-516 (2004-10-07)
Anxiety disorders are among the most common psychological disturbances in the industrialized world. Current behavioral therapy procedures for these disorders are somewhat effective, but their efficacy could be substantially improved. Because these procedures are largely based on the process of
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The American journal of psychiatry, 170(7), 751-758 (2013-04-20)
The authors examined whether D-cycloserine, a partial agonist at the glutamatergic N-methyl-d-aspartate receptor, augments and accelerates a full course of comprehensive cognitive-behavioral therapy (CBT) in adults with generalized social anxiety disorder. This was a multisite randomized placebo-controlled efficacy study with
Michael Davis et al.
Biological psychiatry, 60(4), 369-375 (2006-08-22)
Administration of benzodiazepines or serotonin reuptake inhibitors in combination with behavior therapy for the treatment of many anxiety disorders has generally lead to only modest gains. In this article we suggest that pharmacotherapy aimed not at treating the symptoms of
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Molecular biology and evolution, 32(2), 380-391 (2014-11-13)
Evolutionary innovations are dependent on mutations. Mutation rates are increased by adverse conditions in the laboratory, but there is no evidence that stressful environments that do not directly impact on DNA leave a mutational imprint on extant genomes. Mutational spectra
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