Clevudine

Identification

Generic Name

Clevudine

DrugBank Accession Number

DB06683

Background

Not Available

Type

Small Molecule

Groups

Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Clevudine (DB06683)

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Weight

Average: 260.221
Monoisotopic: 260.08084969

Chemical Formula

C₁₀H₁₃FN₂O₅

Synonyms

• 2'-Fluoro-5-methyl-beta-L-arabinofuranosyluracil
• Clevudine
• L-FMAU

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Pharmacology

Indication

Investigated for use/treatment in hepatitis (viral, B).

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Viral hepatitis b		••••••••••••			•••••••
Treatment of	Viral hepatitis b		••••••••••••		••••••••• •••• •••••••••• •• ••••• ••••••• •••••••••••••••• •••••	•••••••

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Clevudine.
Anthrax vaccine	The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Clevudine.
Bacillus calmette-guerin substrain connaught live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Clevudine.
Bacillus calmette-guerin substrain russian BCG-I live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Clevudine.
Bacillus calmette-guerin substrain tice live antigen	The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Clevudine.

Food Interactions

Not Available

Products

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Categories

ATC Codes

J05AF12 — Clevudine

• J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-Infective Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Arabinonucleosides
• Direct Acting Antivirals
• Nucleic Acids, Nucleotides, and Nucleosides
• Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
• Nucleosides
• Pyrimidine Nucleosides
• Pyrimidines

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Pyrimidones / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Fluorohydrins / Lactams / Azacyclic compounds / Oxacyclic compounds / Organic oxides / Organofluorides / Hydrocarbon derivatives / Organonitrogen compounds / Organopnictogen compounds / Primary alcohols / Alkyl fluorides

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Substituents

Alcohol / Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Fluorohydrin / Halohydrin / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Primary alcohol / Pyrimidine / Pyrimidine 2'-deoxyribonucleoside / Pyrimidone / Secondary alcohol / Tetrahydrofuran / Urea / Vinylogous amide

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Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

IN51MVP5F1

CAS number

163252-36-6

InChI Key

GBBJCSTXCAQSSJ-XQXXSGGOSA-N

InChI

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

IUPAC Name

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

SMILES

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

References

General References

Not Available

External Links

ChemSpider

65894

ChEBI

135964

ChEMBL

CHEMBL458875

ZINC

ZINC000000001484

Wikipedia

Clevudine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Chronic Hepatitis B Infection	3
4	Completed	Treatment	HBeAg(+) Chronic Hepatitis B	1
4	Completed	Treatment	HBeAg(-) Chronic Hepatitis B With Compensated Liver Function	1
4	Completed	Treatment	Hepatitis B Associated Hepatocellular Carcinoma	1
4	Completed	Treatment	Viral Hepatitis B	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule		30 mg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	87.7 mg/mL	ALOGPS
logP	-0.72	ALOGPS
logP	-1.1	Chemaxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	10.1	Chemaxon
pKa (Strongest Basic)	-3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	99.1 Å2	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	55.23 m3·mol-1	Chemaxon
Polarizability	23.2 Å3	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-004l-9410000000-59a959e95b59afa77a49
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0pb9-0940000000-5dae756bbe74fe2418de
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0059-6900000000-c8b53f42cca509af60ac
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-053r-9300000000-53526b4e213d3ba3acc5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-054o-9800000000-a30a1bda498123f31d22
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a6r-2900000000-0ad6cd5ee4c6ba9d63bf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000f-9600000000-f31a71501272ecc6beba
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	163.78072	predicted	DeepCCS 1.0 (2019)
[M+H]+	166.13898	predicted	DeepCCS 1.0 (2019)
[M+Na]+	173.11732	predicted	DeepCCS 1.0 (2019)

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Drug created at March 19, 2008 16:49 / Updated at February 21, 2021 18:52