Catalog Number: 100535, 194788 D-Cycloserine Structure: Molecular Formula: C3H6N2O2 Molecular Weight: 102.1 CAS #: 68-41-7 Synonym: R (+)-4-amino-3-isoxazolidinone: D-4-amino-3-isoxazolidinone Physical Decription: White to off white powder Solubility: Soluble in water (up to 100 mg/ml - clear, colorless to faint yel ow solution), 96% ethanol (1 in 50 parts ethanol); slightly soluble in methanol or propylene glycol; practical y insoluble in chloroform and ether. It is recommened to prepare solutions fresh for each use (neutral and acidic solutions are very unstable); however, aqueous solutions buffered to pH 10 with sodium carbonate may be stored for up to one week if stored at 2-8°C. Mode of Resistance: D-Ala transport interference. Inhibition: Studies in vitro show no suppression of growth in cultures made in media containing D-alanine which appears to block the antibacterial action of D-cycloserine.5 Description: A structural analog of D-Alanine. A partial agonist at the glycine modulatory site of NMDA receptors11,16,19; enhances learning and memory in several models of cognitive deficit4,10,11,12,14,15,16,18; anticonvulsant (at high doses).2,20 Antibiotic against gram-negative bacteria that acts by inhibiting the synthesis of the cel wal (D-Ala peptide bond formation).13
D-Cycloserine has antibiotic activity in vitro against growth phase gram-negative bacteria including Escherichia coli (workingconcentration of approximately 200 ug/ml)13, strains of Staphylococcus aureus, Nocardia species and Chlamydia,5 and somemycobacteria including Mycobacterium tuberculosis. The minimum inhibitory concentrations (MIC) in vitro for M. tuberculosis rangefrom 5-20 ug/ml.
Typical Concentration for Use: 100-200 ug/ml. Prepare just before use using 0.1 M sodium phosphate buffer, pH 8.0. Availability: Catalog Number Description References:
1. Merck Index,12th Ed, No 2820. 2. Chessel , I.P., et al., Brain Res., v. 565, 345 (1991). 3. El-Obeid, H.A. and Al-Badr, A.A., "Analytical Profile of D-Cycloserine" in Analytical Profiles of Drug Substances, v. 18,
Academic Press; New York, p. 567 (1989).
4. Flood, J.F., et al., Eur. J. Pharmacol., v. 221, 249 (1992). 5. Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th Ed., Hardman, J.G., et al. (eds.), p. 1164, McGraw-
6. Jain, M.K., Handbook of Enzyme Inhibitors, John Wiley & Sons; New York, p. 112 (1982). 7. Jones, L.R., Anal. Chem., v. 28, 39 (1956). 8. Kuehl, F.A., Jr., et al., J. Am. Chem. Soc., v. 77, 2344 (1955). 9. Musson, D.G., et al., J. Chromatog.,v. 414, 121 (1987).
10. Nakazato, E., et al., "Cholinergic and glutamatergic activation reverses working memory failure by hippocampal histamine H1
receptor blockade in rats." Life Sci., v. 67, 1139-1147 (2000).
11. Ohno, M. and Watanabe, S., Eur. J. Pharmacol., v. 318, 267 (1996). 12. Pussinen, R. and Sirvio, J., "Effects of D-cycloserine, a positive modulator of N-methyl-D-aspartate receptors, and ST 587, a
putative alpha-1 adrenergic agonist, individual y and in combination, on the non-delayed and delayed foraging behaviour of rats assessed in the radial arm maze." J. Psychopharmacol., v. 13, 171 (1999).
13. Raleigh, E.A., et al., "Selected Topics from Classical Bacterial Genetics" in Short Protocols in Molecular Biology, 4th Ed.,
Ausubel, F.M., et al. (eds.), Unit 1.4, p. 1-9 (John Wiley & Sons, Inc. New York (1999).
14. Schneider, J.S., et al., "Effects of the partial glycine agonist D-cycloserine on cognitive functioning in chronic low dose MPTP-
treated monkeys." Brain Res., v. 860, 190-194 (2000).
15. Schuster, G.M. and Schmidt, W.J., Eur. J. Pharmacol., v. 224, 97 (1992). 16. Sirvio, J., et al., Neurosci. Lett., v. 146, 215 (1992). 17. Stammer, C.H., et al., J. Am. Chem. Soc., v. 77, 2346 (1955). 18. Temple, M.D. and Hamm, R.J., Brain Res., v. 741, 246 (1996). 19. Watson, et al., "D-Cycloserine acts as a partial agonist at the glycine modulatory site of the NMDA receptor expressed in
Xenopus oocytes." Brain Res., v. 510, 158-160 (1990).
20. Wlaz, P., et al., "Influence of D-cycloserine on the anticonvulsant activity of phenytoin and carbamazepine against
electroconvulsions in mice." Epilepsia, v. 37, 610-617 (1996).
BOEHRINGER MANNHEIM / R-BIOPHARM Enzymatic BioAnalysis / Food Analysis UV-method for the determination of ammonia in foodstuffs and other materials and for the determination of nitrogen after Store at 2-8°C Kjeldahl-digestion (see pt. 12.2) Cat. No. 11 112 732 035 For recommendations for methods and standardized procedures seeTest-Combination for approx. 50 determinations Principle
Catalog Number: 100535, 194788