PHR1765
Cycloserine
Pharmaceutical Secondary Standard; Certified Reference Material
Synonym(s):
D-Cycloserine, (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
Beilstein/REAXYS Number:
80798
EC Number:
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.24
Recommended Products
grade
certified reference material
pharmaceutical secondary standard
Quality Level
agency
traceable to USP 1158005
API family
cycloserine
CofA
current certificate can be downloaded
packaging
pkg of 1 g
mp
147 °C (dec.) (lit.)
application(s)
pharmaceutical
format
neat
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
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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.
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
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.
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.
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.
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.
Recommended products
Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
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Description
Pricing
wgk_germany
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
d-Cycloserine
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 457-462 (2015)
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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