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C6880

Sigma-Aldrich

D-Cycloserine

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:
24892907
NACRES:
NA.32

form

powder

Quality Level

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)

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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

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.
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.

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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Hypothesis-driven investigations of diverse pharmacological targets in two mouse models of autism
Rhine MA, et al.
Autism Research : Official Journal of the International Society for Autism Research, 147(1571), 3-3 (2019)
Determination of minimum inhibitory concentration of cycloserine in multidrug resistant Mycobacterium tuberculosis isolates
Singh R
Jordan journal of biological sciences, 147(1571), 1-7 (2014)
D-cycloserine augmented exposure therapy for obsessive-compulsive disorder
Kushner MG, et al.
Biological Psychiatry, 62(8), 835-838 (2007)
Consolidation of human motor cortical neuroplasticity by D-cycloserine
Nitsche MA, et al.
Neuropsychopharmacology, 29(8), 1573-1573 (2004)
D-cycloserine facilitates socially reinforced learning in an animal model relevant to autism spectrum disorders
Modi ME and Young LJ
Biological Psychiatry, 70(3), 298-304 (2011)
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