Azvudine | FNC | RO-0622 | CAS#1011529-10-4 | Reverse Transcriptase Inhibitor

MedKoo Cat#: 528502 | Name: Azvudine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azvudine, also known as FNC and RO-0622, is a reverse transcriptase inhibitor potentially for the treatment of HIV infection. Azvudine showed synergism in combination with six approved anti-HIV drugs on both C8166 and PBMC. Azvudine also showed potent inhibition on NRTI-resistant strains (L74V and T69N). Treatment with Azudine and the protein biosynthesis inhibitor, cycloheximide (CHX), accelerated the inhibition of viral protein synthesis in the HTLV‑1‑infected cells.

Chemical Structure

Azvudine

CAS#1011529-10-4

Theoretical Analysis

MedKoo Cat#: 528502

Name: Azvudine

CAS#: 1011529-10-4

Chemical Formula: C9H11FN6O4

Exact Mass: 286.0826

Molecular Weight: 286.22

Elemental Analysis: C, 37.77; H, 3.87; F, 6.64; N, 29.36; O, 22.36

Price and Availability

Size	Price	Availability
1mg	USD 150.00	Ready to ship
5mg	USD 450.00	Ready to ship
10mg	USD 750.00	Ready to ship
25mg	USD 1,550.00	Ready to ship
50mg	USD 2,550.00	Ready to ship
100mg	USD 3,950.00	Ready to ship

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Related CAS #

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Synonym

Azvudine; FNC; RO-0622; RO 0622; RO0622

IUPAC/Chemical Name

4-amino-1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

InChi Key

KTOLOIKYVCHRJW-XZMZPDFPSA-N

InChi Code

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

SMILES Code

O=C1N=C(N)C=CN1[C@H]2[C@@H](F)[C@@H]([C@](CO)(N=[N+]=[N-])O2)O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#B21B09C26

QC Data

View QC data: current batch, Lot#B21B09C26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Azvudine (RO-0622) hydrochloride is a potent nucleoside reverse transcriptase inhibitor (NRTI), with antiviral activity on HIV, HBV and HCV that exerts highly potent inhibition on HIV-1 (EC50s ranging from 0.03 to 6.92 nM) and HIV-2 (EC50s ranging from 0.018 to 0.025 nM).

In vitro activity:

To evaluate the antiviral activity of Azvudine (FNC), the lab-adaptive strains (IIIB, RF) and clinical strains (KM018, TC-1, WAN) were used to infect HIV sensitive C8166 cells or PHA-stimulated PBMCs and the commercially available NRTI-3TC was used as control. FNC displayed strong inhibition on wild-type HIV-1IIIB and HIV-1RF with the 50% effective concentration values (EC50) ranging from 30 to 110 pM. FNC was about 1835- to 11671-fold more potent than 3TC. FNC was also inhibitory to HIV-2ROD and HIV-2CBL-20 in vitro with EC50 of 0.018 and 0.025 nM respectively. Reference: PLoS One. 2014 Aug 21. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140803/

In vivo activity:

Oral administration of FNC in rats revealed a substantial thymus-homing feature, with FNC triphosphate (the active form) concentrated in the thymus and peripheral blood mononuclear cells (PBMC). Treating SARS-CoV-2 infected rhesus macaques with FNC (0.07 mg/kg, qd, orally) reduced viral load, recuperated the thymus, improved lymphocyte profiles, alleviated inflammation and organ damage, and lessened ground-glass opacities in chest X-ray. Reference: Signal Transduct Target Ther. 2021 Dec 6. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8646019/

	Solvent	mg/mL	mM
Solubility
	H2O	125.0	387.38

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 286.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

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. PMID: 25144636; PMCID: PMC4140803. 2. Xu N, Yang J, Zheng B, Zhang Y, Cao Y, Huan C, Wang S, Chang J, Zhang W. The Pyrimidine Analog FNC Potently Inhibits the Replication of Multiple Enteroviruses. J Virol. 2020 Apr 16;94(9):e00204-20. doi: 10.1128/JVI.00204-20. PMID: 32075935; PMCID: PMC7163137 3. Zhang JL, Li YH, Wang LL, Liu HQ, Lu SY, Liu Y, Li K, Liu B, Li SY, Shao FM, Wang K, Sheng N, Li R, Cui JJ, Sun PC, Ma CX, Zhu B, Wang Z, Wan YH, Yu SS, Che Y, Wang CY, Wang C, Zhang Q, Zhao LM, Peng XZ, Cheng Z, Chang JB, Jiang JD. Azvudine is a thymus-homing anti-SARS-CoV-2 drug effective in treating COVID-19 patients. Signal Transduct Target Ther. 2021 Dec 6;6(1):414. doi: 10.1038/s41392-021-00835-6. PMID: 34873151; PMCID: PMC8646019.

In vitro protocol:

In vivo protocol:

1. Zhang JL, Li YH, Wang LL, Liu HQ, Lu SY, Liu Y, Li K, Liu B, Li SY, Shao FM, Wang K, Sheng N, Li R, Cui JJ, Sun PC, Ma CX, Zhu B, Wang Z, Wan YH, Yu SS, Che Y, Wang CY, Wang C, Zhang Q, Zhao LM, Peng XZ, Cheng Z, Chang JB, Jiang JD. Azvudine is a thymus-homing anti-SARS-CoV-2 drug effective in treating COVID-19 patients. Signal Transduct Target Ther. 2021 Dec 6;6(1):414. doi: 10.1038/s41392-021-00835-6. PMID: 34873151; PMCID: PMC8646019. 2. Xu N, Yang J, Zheng B, Zhang Y, Cao Y, Huan C, Wang S, Chang J, Zhang W. The Pyrimidine Analog FNC Potently Inhibits the Replication of Multiple Enteroviruses. J Virol. 2020 Apr 16;94(9):e00204-20. doi: 10.1128/JVI.00204-20. PMID: 32075935; PMCID: PMC7163137.

1: Zhang JL, Li YH, Wang LL, Liu HQ, Lu SY, Liu Y, Li K, Liu B, Li SY, Shao FM, Wang K, Sheng N, Li R, Cui JJ, Sun PC, Ma CX, Zhu B, Wang Z, Wan YH, Yu SS, Che Y, Wang CY, Wang C, Zhang Q, Zhao LM, Peng XZ, Cheng Z, Chang JB, Jiang JD. Azvudine is a thymus-homing anti-SARS-CoV-2 drug effective in treating COVID-19 patients. Signal Transduct Target Ther. 2021 Dec 6;6(1):414. doi: 10.1038/s41392-021-00835-6. PMID: 34873151; PMCID: PMC8646019. 2: Yu B, Chang J. Azvudine (FNC): a promising clinical candidate for COVID-19 treatment. Signal Transduct Target Ther. 2020 Oct 10;5(1):236. doi: 10.1038/s41392-020-00351-z. PMID: 33040075; PMCID: PMC7547293. 3: Yu B, Chang J. The first Chinese oral anti-COVID-19 drug Azvudine launched. Innovation (Camb). 2022 Nov 8;3(6):100321. doi: 10.1016/j.xinn.2022.100321. Epub 2022 Sep 9. PMID: 36106026; PMCID: PMC9461232. 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 Oct;7(19):e2001435. doi: 10.1002/advs.202001435. Epub 2020 Aug 13. PMID: 35403380; PMCID: PMC7404576. 5: 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. PMID: 25144636; PMCID: PMC4140803. 6: Gao Y, Luo Z, Ren S, Duan Z, Han Y, Liu H, Gao Z, Zhang X, Hu Z, Ma Y. Antiviral effect of azvudine and nirmatrelvir-ritonavir among hospitalized patients with COVID-19. J Infect. 2023 Jun;86(6):e158-e160. doi: 10.1016/j.jinf.2023.03.023. Epub 2023 Mar 30. PMID: 37003523; PMCID: PMC10062713. 7: Li G, Wang Y, De Clercq E. Approved HIV reverse transcriptase inhibitors in the past decade. Acta Pharm Sin B. 2022 Apr;12(4):1567-1590. doi: 10.1016/j.apsb.2021.11.009. Epub 2021 Nov 16. PMID: 35847492; PMCID: PMC9279714. 8: Fayzullina D, Kharwar RK, Acharya A, Buzdin A, Borisov N, Timashev P, Ulasov I, Kapomba B. FNC: An Advanced Anticancer Therapeutic or Just an Underdog? Front Oncol. 2022 Feb 10;12:820647. doi: 10.3389/fonc.2022.820647. PMID: 35223502; PMCID: PMC8867032. 9: Chang J. 4'-Modified Nucleosides for Antiviral Drug Discovery: Achievements and Perspectives. Acc Chem Res. 2022 Feb 15;55(4):565-578. doi: 10.1021/acs.accounts.1c00697. Epub 2022 Jan 25. PMID: 35077644. 10: Sun Y, Jin L, Dian Y, Shen M, Zeng F, Chen X, Deng G. Oral Azvudine for hospitalised patients with COVID-19 and pre-existing conditions: a retrospective cohort study. EClinicalMedicine. 2023 May 5;59:101981. doi: 10.1016/j.eclinm.2023.101981. PMID: 37193346; PMCID: PMC10167478. 11: Dian Y, Meng Y, Sun Y, Deng G, Zeng F. Azvudine versus Paxlovid for oral treatment of COVID-19 in Chinese patients with pre-existing comorbidities. J Infect. 2023 May 17:S0163-4453(23)00290-6. doi: 10.1016/j.jinf.2023.05.012. Epub ahead of print. PMID: 37207823; PMCID: PMC10188372. 12: Deng G, Li D, Sun Y, Jin L, Zhou Q, Xiao C, Wu Q, Sun H, Dian Y, Zeng F, Pan P, Shen M. Real-world effectiveness of Azvudine versus nirmatrelvir-ritonavir in hospitalized patients with COVID-19: A retrospective cohort study. J Med Virol. 2023 Apr;95(4):e28756. doi: 10.1002/jmv.28756. PMID: 37185838. 13: Yang R, Cheng J, Song X, Pan Y, Wang H, Li J, He X, Gou J, Zhang G. Characteristics of COVID-19 (Delta Variant)/HIV Co-infection: A Cross-sectional Study in Henan Province, China. Intensive Care Res. 2022;2(3-4):96-107. doi: 10.1007/s44231-022-00018-z. Epub 2022 Nov 15. PMID: 36407473; PMCID: PMC9666970. 14: Zhang X, Jiao F, Li G, Yu X, Pei Y, Zhang Y, Wang Z, Li P. Elevated INR in a COVID-19 patient after concomitant administration of azvudine and anticoagulants. Front Pharmacol. 2023 May 19;14:1191608. doi: 10.3389/fphar.2023.1191608. PMID: 37274098; PMCID: PMC10235595. 15: Zeng G, Wang L, Li J, Zhang Z. Real-world effectiveness of Azvudine versus nirmatrelvir-ritonavir in hospitalized patients with COVID-19. J Med Virol. 2023 Jun;95(6):e28836. doi: 10.1002/jmv.28836. PMID: 37247396. 16: Yang L, Wang Z. Bench-to-bedside: Innovation of small molecule anti-SARS- CoV-2 drugs in China. Eur J Med Chem. 2023 Sep 5;257:115503. doi: 10.1016/j.ejmech.2023.115503. Epub 2023 May 18. PMID: 37229831; PMCID: PMC10193775. 17: Kale A, Shelke V, Dagar N, Anders HJ, Gaikwad AB. How to use COVID-19 antiviral drugs in patients with chronic kidney disease. Front Pharmacol. 2023 Feb 9;14:1053814. doi: 10.3389/fphar.2023.1053814. PMID: 36843922; PMCID: PMC9947246. 18: Jash R, Prasanth DSNBK, Jash M, Suneetha A. Small molecules in the race of COVID-19 drug development. J Asian Nat Prod Res. 2023 Apr 17:1-22. doi: 10.1080/10286020.2023.2197595. Epub ahead of print. PMID: 37066495. 19: da Silva RM, Gebe Abreu Cabral P, de Souza SB, Arruda RF, Cabral SPF, de Assis ALEM, Martins YPM, Tavares CAA, Viana Junior AB, Chang J, Lei P. Serial viral load analysis by DDPCR to evaluate FNC efficacy and safety in the treatment of mild cases of COVID-19. Front Med (Lausanne). 2023 Mar 14;10:1143485. doi: 10.3389/fmed.2023.1143485. PMID: 37007788; PMCID: PMC10053779. 20: Li Z, Li Z, Yang L, Xie Y, Shi J, Wang R, Chang J. Investigation of the binding between pepsin and nucleoside analogs by spectroscopy and molecular simulation. J Fluoresc. 2015 Mar;25(2):451-63. doi: 10.1007/s10895-015-1532-2. Epub 2015 Feb 27. PMID: 25721993.