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C6880

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:
Molecular Weight:
102.09
UNSPSC Code:
12352209
NACRES:
NA.32
PubChem Substance ID:
EC Number:
200-688-4
Beilstein/REAXYS Number:
80798
MDL number:
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form

powder

Quality Level

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

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[1]
  • 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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1 of 1

This Item
C3909300201158005
antibiotic activity spectrum

Gram-negative bacteria, mycobacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

antibiotic activity spectrum

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

-

form

powder

form

powder

form

powder

form

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

mp

147 °C (dec.) (lit.)

mp

147 °C (dec.) (lit.)

mp

147 °C (dec.) (lit.)

mp

147 °C (dec.) (lit.)

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)

Gene Information

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

Gene Information

-

Gene Information

-


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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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Related Content


D-cycloserine augmented exposure therapy for obsessive-compulsive disorder
Kushner MG, et al.
Biological Psychiatry, 62(8), 835-838 (2007)
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)
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)



Global Trade Item Number

SKUGTIN
C6880-1G04061835556168
C6880-5G04061835556175

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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