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C3909

Sigma-Aldrich

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

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

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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