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Merck

C3909

D-Cycloserine

synthetic

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
68-41-7
Molecular Weight:
102.09
UNSPSC Code:
12352209
NACRES:
NA.28
PubChem Substance ID:
24277962
EC Number:
200-688-4
Beilstein/REAXYS Number:
80798
MDL number:
MFCD00005353

Key Documents

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Product Name

D-Cycloserine, synthetic

InChI key

DYDCUQKUCUHJBH-UWTATZPHSA-N

InChI

1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

SMILES string

N[C@@H]1CONC1=O

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

Quality Level

200

Gene Information

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

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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.

General description

Chemical structure: amino acid derivatives

Other Notes

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

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000504162
0000504162
0000500600
0000500607
0000500600

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L-serine treatment may improve neurorestoration of rats after permanent focal cerebral ischemia potentially through improvement of neurorepair
Sun L, et al.
PLoS ONE, 9(3), e93405-e93405 (2014)
Rick Richardson et al.
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
Stefan G Hofmann et al.
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
Marta Portero-Tresserra et al.
Neurobiology of learning and memory, 100, 1-11 (2012-12-04)
It is well established that D-cycloserine (DCS), a partial agonist of the NMDA receptor glycine site, enhances learning and memory processes. Although the effects of DCS have been especially elucidated in the extinction and reconsolidation of aversive behavioral paradigms or
Kathryn D Baker et al.
Learning & memory (Cold Spring Harbor, N.Y.), 19(10), 461-469 (2012-09-18)
The NMDA receptor partial agonist d-cycloserine (DCS) enhances the extinction of learned fear in rats and exposure therapy in humans with anxiety disorders. Despite these benefits, little is known about the mechanisms by which DCS promotes the loss of fear.
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