Cycloserine | CAS#68-41-7

MedKoo Cat#: 317573 | Name: Cycloserine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cycloserine is an analogue of the amino acid D-alanine with broad-spectrum antibiotic and glycinergic activities. Cycloserine works as an antibiotic by inhibiting cell-wall biosynthesis in bacteria. As a cyclic analogue of D-alanine, cycloserine acts against two crucial enzymes important in the cytosolic stages of peptidoglycan synthesis: alanine racemase (Alr) and D-alanine:D-alanine ligase (Ddl). The first enzyme is a pyridoxal 5'-phosphate-dependent enzyme which converts the L-alanine to the D-alanine form. The second enzyme is involved in joining two of these D-alanine residues together by catalyzing the formation of the ATP-dependent D-alanine-D-alanine dipeptide bond between the resulting D-alanine molecules.

Chemical Structure

Cycloserine

CAS#68-41-7

Theoretical Analysis

MedKoo Cat#: 317573

Name: Cycloserine

CAS#: 68-41-7

Chemical Formula: C3H6N2O2

Exact Mass: 102.0429

Molecular Weight: 102.09

Elemental Analysis: C, 35.29; H, 5.92; N, 27.44; O, 31.34

Price and Availability

Size	Price	Availability
100mg	USD 150.00	Ready to Ship
1g	USD 250.00	Ready to ship
2g	USD 400.00	Ready to ship
5g	USD 650.00	2 Weeks

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Synonym

D-cycloserine; Cycloserine; Seromycin; 68-41-7; Orientomycin; Oxamycin; Seromycin

IUPAC/Chemical Name

(4R)-4-amino-1,2-oxazolidin-3-one

InChi Key

DYDCUQKUCUHJBH-UWTATZPHSA-N

InChi Code

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

SMILES Code

C1[C@H](C(=O)NO1)N

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T7C10I03

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

D-Cycloserine is an antibiotic which targets sequential bacterial cell wall peptidoglycan biosynthesis enzyme and is also a partial NMDA agonist that can improve cognitive functions.

In vitro activity:

The purpose of this study was to explore effective antimicrobials against either Mycobacterium intracellulare or M. avium. 83 nonduplicate clinical MAC isolates were collected from sputum and identified at the species level by PCR and restriction enzyme analysis of the 65 kDa hsp and rpoB genes. Drug susceptibility testing was performed using broth microdilution method. In the study, dcycloserine had high inhibitory activity (<=16 μg/mL) against both M. intracellulare (82.7%) and M. avium (100%),10 M. avium strains (100%) were more susceptible to cycloserine than M. intracellulare strains (82.7%). D-cycloserine was suitable to treat both M. intracellulare- and M. avium-associated diseases. d-cycloserine competitively inhibits two enzymes, alanine racemase (encoded by alr gene) and d-alanine ligase (encoded by ddlA gene) which are essential for peptidoglycan synthesis in the alanine metabolism pathway. The mechanism of resistance to d-cycloserine is unknown in MAC but overexpression of alr and ddlA genes have been reported to confer resistance to d-cycloserine in Mycobacterium smegmatis. Reference: J Microbiol Immunol Infect. 2018 Oct;51(5):636-643. https://pubmed.ncbi.nlm.nih.gov/28705770/

In vivo activity:

This experiment tested whether the improvement in behavior and synaptic transmission seen in Mecp2tm1.1Jae/y mice after treatment with DCS (d-cycloserine ) might be associated with augmented BDNF levels in the brain. First using ELISA, it was found that total BDNF (tBDNF) protein levels in Mecp2tm1.1Jae/y mice were significantly lower in the brainstem (significant interaction, genotype x treatment, F1,25 = 14.04; p = 0.0067), and striatum (main effect of genotype F1,25 = 50.69; p < 0.0001; main effect of treatment, F1,25 = 5.97; p = 0.0425), compared to WT littermates (Fig 4A). DCS treatment significantly increased BDNF levels in both regions, without affecting levels in WT mice (Fig 4A). Surprisingly, DCS treatment had no effect in any of the brain regions (Fig 4B). By contrast, pBDNF was unaltered in the hippocampus but was significantly lower in the brainstem (significant interaction, genotype x treatment, F1,22 = 12.79; p = 0.0017) and striatum (significant interaction, genotype x treatment, F1,24 = 4.459; p = 0.0453). DCS treatment significantly increased pBDNF in both of these regions (Fig 4C). Thus, treatment with DCS may mitigate the severity of some of the neurobehavioral symptoms experienced by patients with Rett syndrome. Reference: PLoS One. 2017; 12(8): e0183026. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5559075/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	9.80
	H2O	23.0	225.29

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 102.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Huang CC, Wu MF, Chen HC, Huang WC. In vitro activity of aminoglycosides, clofazimine, d-cycloserine and dapsone against 83 Mycobacterium avium complex clinical isolates. J Microbiol Immunol Infect. 2018 Oct;51(5):636-643. doi: 10.1016/j.jmii.2017.05.001. Epub 2017 Jun 28. PMID: 28705770. 2. Uda N, Matoba Y, Kumagai T, Oda K, Noda M, Sugiyama M. Establishment of an in vitro D-cycloserine-synthesizing system by using O-ureido-L-serine synthase and D-cycloserine synthetase found in the biosynthetic pathway. Antimicrob Agents Chemother. 2013 Jun;57(6):2603-12. doi: 10.1128/AAC.02291-12. Epub 2013 Mar 25. Erratum in: Antimicrob Agents Chemother. 2015 Dec;59(12):7926. PMID: 23529730; PMCID: PMC3716191. 3. Combs VM, Crispell HD, Drew KL. D-cycloserine 24 and 48 hours after asphyxial cardiac arrest has no effect on hippocampal CA1 neuropathology. J Cereb Blood Flow Metab. 2014 Oct;34(10):1720. doi: 10.1038/jcbfm.2014.135. Epub 2014 Aug 6. PMID: 25099755; PMCID: PMC4269731. 4. Na ES, De Jesús-Cortés H, Martinez-Rivera A, Kabir ZD, Wang J, Ramesh V, Onder Y, Rajadhyaksha AM, Monteggia LM, Pieper AA. D-cycloserine improves synaptic transmission in an animal model of Rett syndrome. PLoS One. 2017 Aug 16;12(8):e0183026. doi: 10.1371/journal.pone.0183026. Erratum in: PLoS One. 2018 Jan 25;13(1):e0192057. PMID: 28813484; PMCID: PMC5559075.

In vitro protocol:

In vivo protocol:

1.Combs VM, Crispell HD, Drew KL. D-cycloserine 24 and 48 hours after asphyxial cardiac arrest has no effect on hippocampal CA1 neuropathology. J Cereb Blood Flow Metab. 2014 Oct;34(10):1720. doi: 10.1038/jcbfm.2014.135. Epub 2014 Aug 6. PMID: 25099755; PMCID: PMC4269731. 2. Na ES, De Jesús-Cortés H, Martinez-Rivera A, Kabir ZD, Wang J, Ramesh V, Onder Y, Rajadhyaksha AM, Monteggia LM, Pieper AA. D-cycloserine improves synaptic transmission in an animal model of Rett syndrome. PLoS One. 2017 Aug 16;12(8):e0183026. doi: 10.1371/journal.pone.0183026. Erratum in: PLoS One. 2018 Jan 25;13(1):e0192057. PMID: 28813484; PMCID: PMC5559075.

1: Sartori SB, Maurer V, Murphy C, Schmuckermair C, Muigg P, Neumann ID, Whittle N, Singewald N. Combined neuropeptide S and D-cycloserine augmentation prevents the return of fear in extinction impaired rodents: advantage of dual vs. single drug approaches. Int J Neuropsychopharmacol. 2015 Dec 1. pii: pyv128. doi: 10.1093/ijnp/pyv128. [Epub ahead of print] PubMed PMID: 26625894. 2: Butler AJ, Kallos J, Housley SN, LaPlaca MC, Traynelis SF, Wolf SL. Randomized, Placebo-Controlled, Double-Blind Pilot Study of D-Cycloserine in Chronic Stroke. Rehabil Res Pract. 2015;2015:534239. doi: 10.1155/2015/534239. Epub 2015 Oct 26. PubMed PMID: 26587287; PubMed Central PMCID: PMC4637506. 3: Uda N, Matoba Y, Kumagai T, Oda K, Noda M, Sugiyama M. Erratum for Uda et al., Establishment of an In Vitro d-Cycloserine-Synthesizing System by Using O-Ureido-l-Serine Synthase and d-Cycloserine Synthetase Found in the Biosynthetic Pathway. Antimicrob Agents Chemother. 2015 Dec;59(12):7926. doi: 10.1128/AAC.02364-15. PubMed PMID: 26578703; PubMed Central PMCID: PMC4649175. 4: Otto MW, Kredlow MA, Smits JA, Hofmann SG, Tolin DF, de Kleine RA, van Minnen A, Evins AE, Pollack MH. Enhancement of Psychosocial Treatment With d-Cycloserine: Models, Moderators, and Future Directions. Biol Psychiatry. 2015 Sep 25. pii: S0006-3223(15)00767-2. doi: 10.1016/j.biopsych.2015.09.007. [Epub ahead of print] Review. PubMed PMID: 26520240. 5: Brom M, Laan E, Everaerd W, Spinhoven P, Trimbos B, Both S. d-Cycloserine reduces context specificity of sexual extinction learning. Neurobiol Learn Mem. 2015 Nov;125:202-10. doi: 10.1016/j.nlm.2015.09.010. Epub 2015 Oct 9. PubMed PMID: 26456134. 6: Malan-Müller S, Fairbairn L, Daniels WM, Dashti MJ, Oakeley EJ, Altorfer M, Kidd M, Seedat S, Gamieldien J, Hemmings SM. Molecular mechanisms of D-cycloserine in facilitating fear extinction: insights from RNAseq. Metab Brain Dis. 2015 Sep 23. [Epub ahead of print] PubMed PMID: 26400817. 7: Olatunji BO, Rosenfield D, Monzani B, Krebs G, Heyman I, Turner C, Isomura K, Mataix-Cols D. EFFECTS OF HOMEWORK COMPLIANCE ON COGNITIVE-BEHAVIORAL THERAPY WITH D-CYCLOSERINE AUGMENTATION FOR CHILDREN WITH OBSESSIVE COMPULSIVE DISORDER. Depress Anxiety. 2015 Dec;32(12):935-43. doi: 10.1002/da.22423. Epub 2015 Sep 15. PubMed PMID: 26372401. 8: Schade S, Paulus W. D-Cycloserine in Neuropsychiatric Diseases: A Systematic Review. Int J Neuropsychopharmacol. 2015 Sep 12. pii: pyv102. doi: 10.1093/ijnp/pyv102. [Epub ahead of print] Review. PubMed PMID: 26364274. 9: Kumagai T, Ozawa T, Tanimoto M, Noda M, Matoba Y, Sugiyama M. High-Level Heterologous Production of d-Cycloserine by Escherichia coli. Appl Environ Microbiol. 2015 Nov 15;81(22):7881-7. doi: 10.1128/AEM.02187-15. Epub 2015 Sep 4. PubMed PMID: 26341210; PubMed Central PMCID: PMC4616934. 10: Chaturvedi SK, Zaidi N, Alam P, Khan JM, Qadeer A, Siddique IA, Asmat S, Zaidi Y, Khan RH. Unraveling Comparative Anti-Amyloidogenic Behavior of Pyrazinamide and D-Cycloserine: A Mechanistic Biophysical Insight. PLoS One. 2015 Aug 27;10(8):e0136528. doi: 10.1371/journal.pone.0136528. eCollection 2015. PubMed PMID: 26312749; PubMed Central PMCID: PMC4552381.