Clevudine (L-FMAU)

Alias: L-FMAU; L FMAU; LFMAU; Clevudine

Cat No.:V1467 Purity: ≥98%

COA Product Data Instructions for use SDS

Clevudine (L-FMAU) Chemical Structure CAS No.: 163252-36-6
Product category: DNA(RNA) Synthesis

This product is for research use only, not for human use. We do not sell to patients.

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50mg
100mg
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Major Universities, Research Institutions, Biotech & Pharma
Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Clevudine (L-FMAU; L FMAU; Levovir and Revovir) is a potent antiviral drug approved in South Korea and the Philippines for the treatment of hepatitis B (HBV) infections with EC50 0.1 μM in HepG2 2.2.15 cells as well as EBV. Numerous cell lines, such as MT2, CEM, H1, HepG2 2.2.15, and bone marrow progenitor cells, exhibit minimal cytotoxicity when exposed to clevodine exposure. In cells, clevudine is broken down into its monophosphate, then into its di- and triphosphates by cellular thymidine kinase and deoxycytidine kinase.

Biological Activity I Assay Protocols (From Reference)

Targets

RNA polymerase; DNA polymerase

ln Vitro

Clenudine is a potent antiviral drug against both EBV and HBV (EC50 0.1 μM in HepG2 2.2.15 cells), with minimal cytotoxicity in MT2, CEM, H1, HepG2 2.2.15, and bone marrow progenitor cells. The cellular thymidine kinase and deoxycytidine kinase break down clevudine into its monophosphate, which is then converted to the di- and triphosphate in cells. The mechanism of action of clevudine is specific to the synthesis of viral DNA; its triphosphate prevents HBV DNA synthesis in a dose-dependent manner without entering the DNA or causing chain termination.[1] The metabolites of these analogs, diphosphate and triphosphate, increase in concentration when clevudine is administered. The D-configuration anomer of clevudine monophosphate (L-FMAUMP) is a better substrate.[2] In cell culture, levudine is easily phosphorylated to the corresponding 5'-triphosphate form of the compound, which affects levudine's mode of action.[3]

ln Vivo

Animal Protocol

N/A

References

[1]. Bioorg Med Chem Lett . 2002 Dec 2;12(23):3459-62.

[2]. Antimicrob Agents Chemother . 2005 May;49(5):2044-9.

[3]. Expert Rev Anti Infect Ther . 2006 Aug;4(4):549-61.

[4]. J Biol Chem . 1995 Aug 11;270(32):19073-7.

[5]. Antimicrob Agents Chemother . 2004 Jul;48(7):2683-92.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C10H13FN2O5

Molecular Weight

260.22

Exact Mass

260.08

Elemental Analysis

C, 46.16; H, 5.04; F, 7.30; N, 10.77; O, 30.74

CAS #

163252-36-6

Related CAS #

163252-36-6(Clevudine)

Appearance

Solid powder

SMILES

CC1=CN(C(=O)NC1=O)[C@@H]2[C@@H]([C@H]([C@@H](O2)CO)O)F

InChi Key

GBBJCSTXCAQSSJ-XQXXSGGOSA-N

InChi Code

InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1

Chemical Name

1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

Synonyms

L-FMAU; L FMAU; LFMAU; Clevudine

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 52~100 mg/mL (199.8~384.3 mM)

Water: ~52 mg/mL (~199.8 mM)<1 mg/mL

Ethanol: ~4 mg/mL (~15.4 mM)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.8429 mL	19.2145 mL	38.4290 mL
	5 mM	0.7686 mL	3.8429 mL	7.6858 mL
	10 mM	0.3843 mL	1.9215 mL	3.8429 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Calculate Reset

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Calculate Reset

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Calculate Reset

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

Calculate Reset

Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT04891302	Completed	Drug: Clevudine Drug: Placebo	COVID-19	Bukwang Pharmaceutical	March 19, 2021	Phase 2
NCT01192854	Completed	Drug: Clevudine Drug: Adefovir	Chronic Hepatitis B	Eisai Co., Ltd.	February 2010	Phase 3
NCT00558818	Completed	Drug: Clevudine	Chronic Hepatitis B	Bukwang Pharmaceutical	June 2007	Phase 4
NCT04347915	Completed	Drug: Clevudine Drug: Placebo	COVID-19	Bukwang Pharmaceutical	May 26, 2020	Phase 2
NCT00558493	Completed	Drug: Clevudine	Chronic Hepatitis B	Bukwang Pharmaceutical	November 2007	Phase 4

Biological Data

Typical metabolism of l-FMAU and d4T in doxycycline (Dox)-induced Tet-On-TMPK RKO cells. Antimicrob Agents Chemother . 2005 May;49(5):2044-9.

Relative amounts of metabolites of l-FMAU and d4T in the doxycycline-induced Tet-On-TMPK RKO cells (data are presented as the means of three independent experiments). Antimicrob Agents Chemother . 2005 May;49(5):2044-9.