Levcycloserine | CAS#339-72-0 | serine palmitoyltransferase inhibitor

MedKoo Cat#: 596543 | Name: Levcycloserine

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Description:

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

Blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase. Cytotoxicity toward neuroblastoma and medulloblastoma cells mediated by suppression of ganglioside synthesis.[1] L-cycloserine is a potent inhibitor of serine palmitoyltransferase, the first step of sphingolipid synthesis.

Chemical Structure

Levcycloserine

CAS#339-72-0

Theoretical Analysis

MedKoo Cat#: 596543

Name: Levcycloserine

CAS#: 339-72-0

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
250mg	USD 285.00	2 Weeks
1g	USD 650.00	2 Weeks
5g	USD 1,250.00	2 Weeks

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Synonym

Levcycloserine; Cyclo-L-serine; Levcicloserina; L-Oxamicina; BRN 0080799;

IUPAC/Chemical Name

(S)-4-aminoisoxazolidin-3-one

InChi Key

DYDCUQKUCUHJBH-REOHCLBHSA-N

InChi Code

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1

SMILES Code

O=C1NOC[C@@H]1N

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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-Cycloserine ((S)-4-Amino-3-isoxazolidone) irreversibly inhibits GABA pyridoxal 5′-phosphate-dependent aminitransferase in E.

In vitro activity:

These results show a time- and concentration-dependent inactivation of MtIlvE by both isomers, with l-cycloserine being a 40-fold better inhibitor of the enzyme. Minimum inhibitory concentration (MIC) studies revealed that l-cycloserine is a 10-fold better inhibitor of Mycobacterium tuberculosis growth than d-cycloserine. Reference: ACS Chem Biol. 2017 May 19;12(5):1235-1244. https://pubmed.ncbi.nlm.nih.gov/28272868/

In vivo activity:

Studies on the effect of long term L-cycloserine treatment on sphingolipid synthesis were performed to determine whether mice could tolerate continued cerebroside reduction and whether or not the synthesis of other sphingolipids would be inhibited. L-cycloserine, when injected at a low dose for a period of two months resulted in significantly reduced brain cerebroside level with little or no reduction in sulfatide, ganglioside, or sphingomyelin levels; liver and spleen glucocerebroside levels were also significantly reduced. The rate of cerebroside synthesis in brain was greatly reduced, whereas synthesis of sulfatides was much less affected by L-cycloserine indicating that a portion of newly synthesized galactocerebroside is shunted to synthesis of sulfatides. Reference: Neurochem Res. 1989 Mar;14(3):245-8. https://pubmed.ncbi.nlm.nih.gov/2725825/

	Solvent	mg/mL	mM
Solubility
	DMSO	7.2	70.20
	PBS (pH 7.2)	10.0	97.95
	Water	16.7	163.23

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. Amorim Franco TM, Favrot L, Vergnolle O, Blanchard JS. Mechanism-Based Inhibition of the Mycobacterium tuberculosis Branched-Chain Aminotransferase by d- and l-Cycloserine. ACS Chem Biol. 2017 May 19;12(5):1235-1244. doi: 10.1021/acschembio.7b00142. Epub 2017 Mar 16. PMID: 28272868; PMCID: PMC5834943. 2. Sundaram KS, Lev M. Comparative inhibition of bacterial and microsomal 3-ketodihydrosphingosine synthetases by L-cycloserine and other inhibitors. Antimicrob Agents Chemother. 1984 Aug;26(2):211-3. doi: 10.1128/AAC.26.2.211. PMID: 6486763; PMCID: PMC284122. 3. Sundaram KS, Lev M. The long-term administration of L-cycloserine to mice: specific reduction of cerebroside level. Neurochem Res. 1989 Mar;14(3):245-8. doi: 10.1007/BF00971318. PMID: 2725825. 4. Williams RD, Sgoutas DS, Zaatari GS, Santoianni RA. Inhibition of serine palmitoyltransferase activity in rabbit aorta by L-cycloserine. J Lipid Res. 1987 Dec;28(12):1478-81. PMID: 3430071.

In vitro protocol:

In vivo protocol:

1. Sundaram KS, Lev M. The long-term administration of L-cycloserine to mice: specific reduction of cerebroside level. Neurochem Res. 1989 Mar;14(3):245-8. doi: 10.1007/BF00971318. PMID: 2725825. 2. Williams RD, Sgoutas DS, Zaatari GS, Santoianni RA. Inhibition of serine palmitoyltransferase activity in rabbit aorta by L-cycloserine. J Lipid Res. 1987 Dec;28(12):1478-81. PMID: 3430071.

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