NAV

Azvudine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Azvudine
DrugBank Accession Number
DB16407
Background

Azvudine is under investigation in clinical trial NCT04668235 (Study on Safety and Clinical Efficacy of AZVUDINE in COVID-19 Patients (Sars-cov-2 Infected)).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 286.223
Monoisotopic: 286.082581021
Chemical Formula
C9H11FN6O4
Synonyms
  • Azvudine
External IDs
  • FNC
  • HY-19314
  • RO 0622
  • RO-0622
  • SB17040
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Azvudine is a nucleoside reverse transcriptase inhibitor that acts against HIV, HBV, and HCV. Some studies also show that it is able to modulate the expression of proteins like P-glycoprotein (P-gp), MRP2, and BCRP; in one instance, it was also able to increase the activity of P-gp. In 2020, the compound was tested in numerous clinical trials for the treatment of mild and common COVID-19.

TargetActionsOrganism
UATP-binding cassette sub-family G member 2
regulator
Humans
UCanalicular multispecific organic anion transporter 1
regulator
Humans
UP-glycoprotein 1
activator
regulator
Humans
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
Not Available

Interactions

Drug Interactions
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
IJ2XP0ID0K
CAS number
1011529-10-4
InChI Key
KTOLOIKYVCHRJW-XZMZPDFPSA-N
InChI
InChI=1S/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/m0/s1
IUPAC Name
4-amino-1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@@](CO)(N=[N+]=[N-])[C@@H](O)[C@@H]1F

References

General References
  1. Wang RR, Yang QH, Luo RH, Peng YM, Dai SX, Zhang XJ, Chen H, Cui XQ, Liu YJ, Huang JF, Chang JB, Zheng YT: Azvudine, a novel nucleoside reverse transcriptase inhibitor showed good drug combination features and better inhibition on drug-resistant strains than lamivudine in vitro. PLoS One. 2014 Aug 21;9(8):e105617. doi: 10.1371/journal.pone.0105617. eCollection 2014. [Article]
  2. Liu Y, Wang Y, Peng Y, Liu B, Ma F, Jiang J, Wang Q, Chang J: Effects of the antiretroviral drug 2'-deoxy-2'-beta-fluoro-4'-azidocytidine (FNC) on P-gp, MRP2 and BCRP expressions and functions. Pharmazie. 2018 Sep 1;73(9):503-507. doi: 10.1691/ph.2018.8555. [Article]
  3. Liu Y, Liu B, Zhang Y, Peng Y, Huang C, Wang N, Jiang J, Wang Q, Chang J: Intestinal absorption mechanisms of 2'-deoxy-2'-beta-fluoro-4'-azidocytidine, a cytidine analog for AIDS treatment, and its interaction with P-glycoprotein, multidrug resistance-associated protein 2 and breast cancer resistance protein. Eur J Pharm Sci. 2017 Jul 15;105:150-158. doi: 10.1016/j.ejps.2017.05.009. Epub 2017 May 6. [Article]
  4. Ren Z, Luo H, Yu Z, Song J, Liang L, Wang L, Wang H, Cui G, Liu Y, Wang J, Li Q, Zeng Z, Yang S, Pei G, Zhu Y, Song W, Yu W, Song C, Dong L, Hu C, Du J, Chang J: A Randomized, Open-label, Controlled Clinical Trial of Azvudine Tablets in the Treatment of Mild and Common COVID-19, A Pilot Study. Adv Sci (Weinh). 2020 Jul 14:2001435. doi: 10.1002/advs.202001435. [Article]
ChemSpider
24717759
ChEMBL
CHEMBL519846
Wikipedia
Azvudine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19)1
3CompletedTreatmentCoronavirus Disease 2019 (COVID‑19)2
3Unknown StatusTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
2RecruitingPreventionCoronavirus Disease 2019 (COVID‑19)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.8 mg/mLALOGPS
logP0.06ALOGPS
logP-1.3Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.04Chemaxon
pKa (Strongest Basic)3.78Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area137.81 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity60.61 m3·mol-1Chemaxon
Polarizability24.31 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. ATP-binding cassette sub-family G member 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Liu Y, Liu B, Zhang Y, Peng Y, Huang C, Wang N, Jiang J, Wang Q, Chang J: Intestinal absorption mechanisms of 2'-deoxy-2'-beta-fluoro-4'-azidocytidine, a cytidine analog for AIDS treatment, and its interaction with P-glycoprotein, multidrug resistance-associated protein 2 and breast cancer resistance protein. Eur J Pharm Sci. 2017 Jul 15;105:150-158. doi: 10.1016/j.ejps.2017.05.009. Epub 2017 May 6. [Article]
Details2. Canalicular multispecific organic anion transporter 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Liu Y, Liu B, Zhang Y, Peng Y, Huang C, Wang N, Jiang J, Wang Q, Chang J: Intestinal absorption mechanisms of 2'-deoxy-2'-beta-fluoro-4'-azidocytidine, a cytidine analog for AIDS treatment, and its interaction with P-glycoprotein, multidrug resistance-associated protein 2 and breast cancer resistance protein. Eur J Pharm Sci. 2017 Jul 15;105:150-158. doi: 10.1016/j.ejps.2017.05.009. Epub 2017 May 6. [Article]
Details3. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
Regulator
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Liu Y, Liu B, Zhang Y, Peng Y, Huang C, Wang N, Jiang J, Wang Q, Chang J: Intestinal absorption mechanisms of 2'-deoxy-2'-beta-fluoro-4'-azidocytidine, a cytidine analog for AIDS treatment, and its interaction with P-glycoprotein, multidrug resistance-associated protein 2 and breast cancer resistance protein. Eur J Pharm Sci. 2017 Jul 15;105:150-158. doi: 10.1016/j.ejps.2017.05.009. Epub 2017 May 6. [Article]

Drug created at December 23, 2020 16:49 / Updated at December 23, 2021 07:46