Azvudine
Explore a selection of our essential drug information below, or:
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
- Weight
- Average: 286.223
Monoisotopic: 286.082581021 - Chemical Formula
- C9H11FN6O4
- Synonyms
- Azvudine
- External IDs
- FNC
- HY-19314
- RO 0622
- RO-0622
- SB17040
Pharmacology
- Indication
Not Available
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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.
Target Actions Organism UBroad substrate specificity ATP-binding cassette transporter ABCG2 regulatorHumans UATP-binding cassette sub-family C member 2 regulatorHumans UATP-dependent translocase ABCB1 activatorregulatorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 24717759
- ChEMBL
- CHEMBL519846
- Wikipedia
- Azvudine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide Not Available Completed Not Available Azvudine / Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide Not Available Not Yet Recruiting Not Available Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Coronavirus Disease 2019 (COVID‑19) / COVID-19 Respiratory Infection 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 11.8 mg/mL ALOGPS logP 0.06 ALOGPS logP -1.3 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 12.04 Chemaxon pKa (Strongest Basic) 3.78 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 137.81 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 60.61 m3·mol-1 Chemaxon Polarizability 24.31 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 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- ATP-binding cassette sub-family C member 2
- Molecular Weight
- 174205.64 Da
References
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- ActivatorRegulator
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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