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
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
Safety
- Toxicity
- LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)
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.
N-Bromosuccinimide Price
- Product number
- C574150
- Product name
- Clevudine
- Packaging
- 1g
- Price
- $895
- Updated
- 2021/12/16
- Product number
- orb134390
- Product name
- Clevudine (Levovir)
- Purity
- >99%
- Packaging
- 250mg
- Price
- $912.9
- Updated
- 2021/12/16
- Product number
- 18571
- Product name
- Clevudine
- Packaging
- 5mg
- Price
- $950
- Updated
- 2021/12/16
- Product number
- orb134390
- Product name
- Clevudine (Levovir)
- Purity
- >99%
- Packaging
- 1g
- Price
- $1802
- Updated
- 2021/12/16
- Product number
- orb134390
- Product name
- Clevudine (Levovir)
- Purity
- >99%
- Packaging
- 100mg
- Price
- $606.9
- Updated
- 2021/12/16
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
- 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
- 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
- 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