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PHR1765

Supelco

Cycloserine

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):
4-Amino-3-isoxazolidinone, D-Cycloserine, (R)-4-Amino-3-isoxazolidone
Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
Molecular Weight:
102.09
Beilstein:
80798
EC Number:
MDL number:

Quality Level

grade

certified reference material
pharmaceutical secondary standard

CofA

current certificate can be downloaded

packaging

pkg of 1 g

mp

147 °C (dec.) (lit.)

application(s)

pharmaceutical

format

neat

pharmacopeia traceability

traceable to USP 1158005

storage temp.

-10 to -25°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

Cycloserine is a broad-spectrum antibiotic commonly produced by certain strains of Streptomyces orchidaceus or S. garphalus. It is used as a second-line drug treatment for multiple drug-resistant strains of Mycobacterium tuberculosis.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Cycloserine may be used as a pharmaceutical reference standard for the determination of the analyte in bulk drug and pharmaceutical formulations by high performance liquid chromatography.

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.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA8432 in the Documents slot below. This is an example certificate only and may not be the lot that you receive.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

d-Cycloserine
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 457-462 (2015)
Development of a liquid chromatographic method for the determination of related substances and assay of d-cycloserine
Pendela M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 47(4-5), 807-811 (2008)
Development and validation of indirect RP-HPLC method for enantiomeric purity determination of d-cycloserine drug substance
Karthikeyan K, et al.
Journal of Pharmaceutical and Biomedical Analysis, 54(4), 850-854 (2011)
S David
The Journal of antimicrobial chemotherapy, 47(2), 203-206 (2001-02-07)
D-Cycloserine (DCS) is a peptidoglycan inhibitor. Although very effective against Mycobacterium tuberculosis, it is seldom employed in the management of this infection due to its high toxicity. beta-Chloro-D-alanine (another peptidoglycan inhibitor) reduces the MIC of DCS from 50 to 2.5

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