Clevudine

ChemicalBook > CAS DataBase List > Clevudine

Product Name: Clevudine
CAS No.: 163252-36-6
Chemical Name: Clevudine
Synonyms: L-FMAU;Levovir;CLEVUDINE;Clevudine CAS;2'-F-2'-ara-dT;Clevudine(Levovir);Clevudine USP/EP/BP;2'-Fluoro-5-methylarabinosyluracil;1-(2''-DEOXY-2''-FLUORO--L-ARABINOFURANOSYL)-5-METHYLURACIL;1-(2'-DEOXY-2'-FLUORO-BETA-L-ARABINOFURANOSYL)-5-METHYLURACIL
CBNumber: CB0839271
Molecular Formula: C10H13FN2O5
Formula Weight: 260.22
MOL File: 163252-36-6.mol

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Clevudine Property

Melting point:: 184-185°
alpha: D25 -111.77° (c = 0.23 in methanol)
Density: 1.55±0.1 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 9.55±0.10(Predicted)
color: White
CAS DataBase Reference: 163252-36-6

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Safety

Toxicity: LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

TRC

Product number: C574150
Product name: Clevudine
Packaging: 1g
Price: $895
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb134390
Product name: Clevudine (Levovir)
Purity: >99%
Packaging: 250mg
Price: $912.9
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 18571
Product name: Clevudine
Packaging: 5mg
Price: $950
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb134390
Product name: Clevudine (Levovir)
Purity: >99%
Packaging: 1g
Price: $1802
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb134390
Product name: Clevudine (Levovir)
Purity: >99%
Packaging: 100mg
Price: $606.9
Updated: 2021/12/16

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Clevudine Chemical Properties,Usage,Production

Description

Clevudine is a fluorinated b-L-nucleoside analog launched for the oral treatment of chronic HBV infection. It is the fifth nucleoside or nucleotide analog to be marketed for this indication. The previous drugs from this class include lamivudine, adefovir, entecavir, and telbivudine. In HBV-expressing human hepatoma cell line 2.2.15, clevudine inhibits HBV DNA synthesis with an EC₅₀ of 0.1 μM, and does not show cytotoxicity up to 200 μM. It is phosphorylated by cellular kinases to the active triphosphate derivative, which subsequently inhibits HBV DNA polymerase and HBV replication. 466 Shridhar Hegde and Michelle Schmidt Clevudine-5′-triphosphate has an intracellular half-life of 16.5 h. Interestingly, it is a non-competitive inhibitor of viral polymerase, and inhibits HBV replication without being incorporated into the DNA. The pharmacokinetic profile of clevudine was linear with a plasma half-life of approximately 60 h. Clevudine was undetectable in plasma after 4 weeks following the cessation of dosing.The most common adverse events reported with clevudine treatment include infection, asthenia, dyspepsia, abdominal pain, headache, and diarrhea.
Clevudine is chemically derived from L-ribose by first incorporating acyl protective groups to produce 1-O-acetyl-2,3,5-tri-O-benzoyl-b-L-ribofuranose intermediate, which is then converted to 1,3,5-tri-O-benzoyl-a-L-ribofuranose in two steps by treating To Market, To Market 2007 467 with hydrogen chloride and subsequent hydrolysis and acyl migration. The remaining steps leading to clevudine include conversion of the C2-hydroxy group to C2-fluoro group with triethylamine trihydrofluoride, formation of the corresponding ribofuranosyl bromide intermediate with hydrogen bromide and acetic acid, condensation with silylated thymine, and removal of benzoyl protective groups with methanolic ammonia.

Chemical Properties

White Solid

Originator

University of Georgia/ Yale University (US)

Uses

Antiviral drug, used for the treatment of Hepatitis B.

Definition

ChEBI: Clevudine is a pyrimidine 2'-deoxyribonucleoside.

brand name

Levovir

Synthesis

The synthesis is depicted in the scheme. L-Arabinose (27) was treated with acetic anhydride and pyridine at room temperature for four hours to give acetylated arabinose, which was then brominated using 30% HBr in AcOH/Ac2O at room temperature for 36 hours to afford bromo-sugar 28 as a white solid in 57% yield after crystallization in ethyl ether. Bromo-sugar 28 was then treated with Zn dust, CuSO4 and NaOAc in AcOH/H2O, followed by chromatographic separation to give L-arabinal 29 in 60% yield. L-arabinal 29 was converted to the fluoro derivative in 70% crude yield by reaction with Selectfluor® (FTEDA- BF4) in refluxing nitromethane/H2O, and the resulting fluoroalcohol was deacetylated with NaOMe in MeOH to give compound 30 in 100% crude yield. Compound 30 was then treated with H2SO4 in refluxing MeOH to afford methyl furanoside 31 in 80% crude yield. Furanoside 31 was benzoylated with benzoyl chloride in pyridine to give a mixture of isomers, from which the |á-anomer was isolated by chromatography and then brominated with 30% HBr/AcOH in CH2Cl2 to provide the crude bromo-sugar 32 which was dissolved in chloroform and used without further purification in the next step. Compound 34 was obtained by treatment of thymine (33) with HMDS and ammonium sulfate in refluxing chloroform for 16 hours. The sugar 32 was condensed with silylated pyrimidine derivative 34 in refluxing chloroform to afford 3,5-di-O-benzoylclevudine in 42% yield after recrystallization from ethanol. The benzoyl groups were removed upon treatment with n-butylamine in refluxing methanol to give clevudine (IV) in 82% yield.

Clevudine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Clevudine manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: Clevudine 163252-36-6
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-23

Honest Joy Holdings Limited

Product: Clevudine 163252-36-6
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98.9%
Supply Ability: 100 tons
Release date: 2022-02-08

Dideu Industries Group Limited

Product: Clevudine 163252-36-6
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons Min
Release date: 2021-07-15

163252-36-6, ClevudineRelated Search:

CHLOROPHOSPHONAZO III Uracil Abacavir Adefovir Potassium pyrophosphate Dimethyl fumarate Emtricitabine Thymosin Adefovir dipivoxil Sofosbuvir Tenofovir disoproxil Tenofovir Zidovudine Dideoxyinosine 2'-Deoxy-L-thymidine Fluorine Clevudine 1-(2'-FLUORO-2'-DEOXY-BETA-L-ARABINOFURANOSYL)-5-METHYLURACIL, [5-3H]-

1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

CLEVUDINE

1-(2'-DEOXY-2'-FLUORO-BETA-L-ARABINOFURANOSYL)-5-METHYLURACIL

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

2'-Fluoro-5-methylarabinosyluracil

Levovir

1-(2''-DEOXY-2''-FLUORO--L-ARABINOFURANOSYL)-5-METHYLURACIL

CLEVUDINE: 1-(2''-DEOXY-2''-FLUORO-BETA-L-ARABINOFURANOSYL)-5-METHYLURACIL

CLEVUDINE: 1-(2''-DEOXY-2''-FLUORO-SS-L-ARABINOFURANOSYL)-5-METHYLURACIL

CLEVUDINE, 1-(2'-DEOXY-2'-FLUORO-β-L-ARABINOFURANOSYL)-5-METHYLURACIL

1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-methylol-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-quinone

1-(2-Deoxy-2-fluoro-β-L-arabinofuranosyl)-5-Methyl-2,4(1H,3H)-pyriMidinedione

L-FMAU

Clevudine(Levovir)

1-((2S,3R,4S,5S)-3-Fluoro-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione

1-((2S,3R,4S,5S)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4

1-((2S,3R,4S,5S)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-

2'-F-2'-ara-dT

2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)-5-methyl-

Clevudine USP/EP/BP

1-[(2S,3R,4S,5S)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)-2-tetrahydrofuryl]-5-methylpyrimidine-2,4(1H,3H)-dione

Clevudine CAS

163252-36-6

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