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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

Molecular Weight:: 260.22

MOL File:: 163252-36-6.mol

MSDS File:: SDS

Modify Date:: 2023/5/18 11:31:03

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Clevudine Properties

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

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H332-H335
Precautionary statements	P280-P305+P351+P338-P310
Toxicity	LD50 in mice, rats (mg/kg): >5000, >3000 orally (Painter)

Clevudine Chemical Properties,Uses,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

Uses

Antiviral drug, used for the treatment of Hepatitis B.

Clevudine Preparation Products And Raw materials

Raw materials

Preparation Products

Clevudine Suppliers

Global( 157)Suppliers

Supplier	Tel	Country	ProdList	Advantage	Inquiry
A.J Chemicals	91-9810153283	New Delhi, India	6124	58	Inquiry
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	China	29798	60	Inquiry
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	China	21669	55	Inquiry
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	China	9337	55	Inquiry
career henan chemical co	+86-0371-86658258 +8613203830695	China	29897	58	Inquiry
BOC Sciences	+1-631-485-4226	United States	19553	58	Inquiry
Chongqing Chemdad Co., Ltd	+86-023-6139-8061 +86-86-13650506873	China	39916	58	Inquiry
CONIER CHEM AND PHARMA LIMITED	+8618523575427	China	49391	58	Inquiry
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd	+8613580539051	CHINA	21149	58	Inquiry
SIMAGCHEM CORP	+86-13806087780	China	17367	58	Inquiry

Supplier	Advantage
A.J Chemicals	58
Capot Chemical Co.,Ltd.	60
Henan Tianfu Chemical Co.,Ltd.	55
Hangzhou FandaChem Co.,Ltd.	55
career henan chemical co	58
BOC Sciences	58
Chongqing Chemdad Co., Ltd	58
CONIER CHEM AND PHARMA LIMITED	58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd	58
SIMAGCHEM CORP	58

Mechanism and Toxicity of Clevudine
Clevudine (L-FMAU) is the unnatural L-enantiomer of the natural nucleoside D-thymidine and has potent antiviral activity again....
Apr 8，2022

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Fluorine Clevudine 1-(2'-FLUORO-2'-DEOXY-BETA-L-ARABINOFURANOSYL)-5-METHYLURACIL, [5-3H]-

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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 1-[(2S,3R,4S,5S)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione 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 Inhibitors API Bases & Related Reagents Intermediates & Fine Chemicals Nucleotides Pharmaceuticals