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Clevudine

Clevudine structure

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

MDL Number:: MFCD00935785

MOL File:: 163252-36-6.mol

MSDS File:: SDS

Last updated:2023-05-18 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
FDA UNII	IN51MVP5F1
NCI Drug Dictionary	clevudine
ATC code	J05AF12

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 price More Price(27)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
TRC	C574150	Clevudine	163252-36-6	1g	$895	2021-12-16	Buy
Biorbyt Ltd	orb134390	Clevudine (Levovir) >99%	163252-36-6	250mg	$912.9	2021-12-16	Buy
Medical Isotopes, Inc.	18571	Clevudine	163252-36-6	5mg	$950	2021-12-16	Buy
Biorbyt Ltd	orb134390	Clevudine (Levovir) >99%	163252-36-6	1g	$1802	2021-12-16	Buy
Biorbyt Ltd	orb134390	Clevudine (Levovir) >99%	163252-36-6	100mg	$606.9	2021-12-16	Buy

Product number	Packaging	Price	Buy
C574150	1g	$895	Buy
orb134390	250mg	$912.9	Buy
18571	5mg	$950	Buy
orb134390	1g	$1802	Buy
orb134390	100mg	$606.9	Buy

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

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.

Synthesis_163252-36-6

Clevudine Preparation Products And Raw materials

Raw materials

Preparation Products

Clevudine Suppliers

Global( 154)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	fandachem@gmail.com	China	9348	55
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49390	58
Shaanxi Dideu Medichem Co. Ltd	18192627656	1012@dideu.com	China	3422	58
Antai Fine Chemical Technology Co.,Limited	18503026267	info@antaichem.com	CHINA	9641	58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd	+8613580539051	joe@yuhengpharm.com	CHINA	21149	58

Supplier	Advantage
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
Shaanxi Dideu Medichem Co. Ltd	58
Antai Fine Chemical Technology Co.,Limited	58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd	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

View Lastest Price from Clevudine manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2022-09-24	Clevudine 163252-36-6	US $0.00-0.00 / kg	1kg	98%	1Ton	Henan Aochuang Chemical Co.,Ltd.
2022-02-10	Clevudine 163252-36-6	US $0.00 / KG	1KG	98.9%	100 tons	Honest Joy Holdings Limited
2021-07-16	Clevudine USP/EP/BP 163252-36-6	US $1.10 / g	1g	99.9%	100 Tons Min	Dideu Industries Group Limited

Clevudine
163252-36-6
US $0.00-0.00 / kg
98%
Henan Aochuang Chemical Co.,Ltd.

Clevudine
163252-36-6
US $0.00 / KG
98.9%
Honest Joy Holdings Limited

Clevudine USP/EP/BP
163252-36-6
US $1.10 / g
99.9%
Dideu Industries Group Limited

163252-36-6(Clevudine)Related Search:

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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