Umifenovir HCl
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MedKoo CAT#: 319804

CAS#: 131707-23-8 (HCl)

Description: Umifenovir, also known as arbidol, is an antiviral treatment used in Russia and Chinafor influenza infection. Since 2005 it has been the number one best-selling over-the-counter drug in Russia. Umifenovir inhibits membrane fusion. Umifenovir prevents contact between the virus and target host cells. Fusion between the viral capsid and the cell membrane of the target cell is inhibited. This prevents viral entry to the target cell, and therefore protects it from infection.


Chemical Structure

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Umifenovir HCl
CAS# 131707-23-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 319804
Name: Umifenovir HCl
CAS#: 131707-23-8 (HCl)
Chemical Formula: C22H26BrClN2O3S
Exact Mass:
Molecular Weight: 513.88
Elemental Analysis: C, 51.42; H, 5.10; Br, 15.55; Cl, 6.90; N, 5.45; O, 9.34; S, 6.24

Price and Availability

Size Price Availability Quantity
50.0mg USD 90.0 Ready to ship
1.0g USD 150.0 Ready to ship
2.0g USD 250.0 Ready to ship
5.0g USD 450.0 Ready to ship
20.0g USD 1250.0 Ready to ship
50.0g USD 1850.0 Ready to ship
100.0g USD 2950.0 Ready to ship
200.0g USD 4650.0 Ready to ship
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Related CAS #: 131707-23-8 (HCl)   131707-25-0 (free base)   868364-57-2 (HCl hydrate)    

Synonym: Umifenovir; Umifenovir HCl; Umifenovir hydrochloride; arbidol.

IUPAC/Chemical Name: ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-1H-indole-3-carboxylate hydrochloride

InChi Key: OMZHXQXQJGCSKN-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H25BrN2O3S.ClH/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3;/h6-11,26H,5,12-13H2,1-4H3;1H

SMILES Code: O=C(C1=C(CSC2=CC=CC=C2)N(C)C3=C1C(CN(C)C)=C(O)C(Br)=C3)OCC.[H]Cl

Appearance: White to off-white crystalline powder

Purity: >98% (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, not in water

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

Biological target: Umifenovir hydrochloride is a broad-spectrum antiviral that is used as an anti-influenza virus agent.
In vitro activity: ARB (arbidol) inhibits multiple enveloped viruses in vitro and the primary mode of action is inhibition of virus entry and/or fusion of viral membranes with intracellular endosomal membranes. ARB is also an effective inhibitor of non-enveloped poliovirus types 1 and 3. In the current report, the antiviral potential of ARB against another picornavirus, foot-and-mouth disease virus (FMDV), a member of the genus is evaluated. Aphthovirus and an important veterinary pathogen. ARB inhibits the replication of FMDV RNA subgenomic replicons. ARB inhibition of FMDV RNA replication is not a result of generalized inhibition of cellular uptake of cargo, such as transfected DNA, and ARB can be added to cells up to 3 h post-transfection of FMDV RNA replicons and still inhibit FMDV replication. ARB prevents the recovery of FMDV replication upon withdrawal of the replication inhibitor guanidine hydrochloride (GuHCl). Although restoration of FMDV replication is known to require de novo protein synthesis upon GuHCl removal, ARB does not suppress cellular translation or FMDV internal ribosome entry site (IRES)-driven translation. ARB also inhibits infection with the related Aphthovirus, equine rhinitis A virus (ERAV). Collectively, the data demonstrate that ARB can inhibit some non-enveloped picornaviruses. Reference: J Gen Virol. 2019 Sep;100(9):1293-1302. https://pubmed.ncbi.nlm.nih.gov/31162013/
In vivo activity: Here, a mouse model of bleomycin-induced pulmonary fibrosis and a mouse model of fecal dilution-induced sepsis to evaluate the effects of arbidol on pulmonary fibrosis and cytokine storm were used. As showed in Figures 2A,B, compared with model group, arbidol significantly decreased Ri, but have no effect of Re. Arbidol could reduce the airway resistance induced by BLM in mice, and thus alleviate the pulmonary function impairment caused by pulmonary fibrosis in mice. Cldyn is often used to detect the elastic resilience of lung tissue and determine the severity of obstructive lung disease As showed in Figures 2C,D, compared with the model group, arbidol significantly increased Cldyn and FVC. These data suggested arbidol could restore some lung function impairment indicators in pulmonary fibrosis mice. Treatment with arbidol promoted reduced sepsis severity 48 h after sepsis induction, based on weight, murine sepsis score and survival rate. Arbidol observably alleviates inflammatory infiltrates and injury in the lungs and liver. Finally, it was also found that arbidol reduced serum levels of pro-inflammatory factors such as TNF-α and IL-6 induced by fecal dilution. In conclusion, the results indicate that arbidol can alleviate the severity of pulmonary fibrosis and sepsis, and provide some reference for the treatment of cytokine storm and sequelae of pulmonary fibrosis in patients with COVID-19. Reference: Front Pharmacol. 2021 Jan 27;11:607075. https://pubmed.ncbi.nlm.nih.gov/33584285/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 48.5 94.38
Ethanol 28.0 54.49

Preparing Stock Solutions

The following data is based on the product molecular weight 513.88 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.

Recalculate based on batch purity %
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. Haviernik J, Štefánik M, Fojtíková M, Kali S, Tordo N, Rudolf I, Hubálek Z, Eyer L, Ruzek D. Arbidol (Umifenovir): A BroadSpectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses. Viruses. 2018 Apr 10;10(4):184. doi: 10.3390/v10040184. PMID: 29642580; PMCID: PMC5923478. 2. Herod MR, Adeyemi OO, Ward J, Bentley K, Harris M, Stonehouse NJ, Polyak SJ. The broad-spectrum antiviral drug arbidol inhibits foot-and-mouth disease virus genome replication. J Gen Virol. 2019 Sep;100(9):1293-1302. doi: 10.1099/jgv.0.001283. Epub 2019 Jun 4. PMID: 31162013. 3. Haviernik J, Štefánik M, Fojtíková M, Kali S, Tordo N, Rudolf I, Hubálek Z, Eyer L, Ruzek D. Arbidol (Umifenovir): A BroadSpectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses. Viruses. 2018 Apr 10;10(4):184. doi: 10.3390/v10040184. PMID: 29642580; PMCID: PMC5923478. 4. Herod MR, Adeyemi OO, Ward J, Bentley K, Harris M, Stonehouse NJ, Polyak SJ. The broad-spectrum antiviral drug arbidol inhibits foot-and-mouth disease virus genome replication. J Gen Virol. 2019 Sep;100(9):1293-1302. doi: 10.1099/jgv.0.001283. Epub 2019 Jun 4. PMID: 31162013
In vitro protocol: 1. Haviernik J, Štefánik M, Fojtíková M, Kali S, Tordo N, Rudolf I, Hubálek Z, Eyer L, Ruzek D. Arbidol (Umifenovir): A BroadSpectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses. Viruses. 2018 Apr 10;10(4):184. doi: 10.3390/v10040184. PMID: 29642580; PMCID: PMC5923478. 2. Herod MR, Adeyemi OO, Ward J, Bentley K, Harris M, Stonehouse NJ, Polyak SJ. The broad-spectrum antiviral drug arbidol inhibits foot-and-mouth disease virus genome replication. J Gen Virol. 2019 Sep;100(9):1293-1302. doi: 10.1099/jgv.0.001283. Epub 2019 Jun 4. PMID: 31162013.
In vivo protocol: 1. Li H, Liu R, Zhang R, Zhang S, Wei Y, Zhang L, Zhou H, Yang C. Protective Effect of Arbidol Against Pulmonary Fibrosis and Sepsis in Mice. Front Pharmacol. 2021 Jan 27;11:607075. doi: 10.3389/fphar.2020.607075. PMID: 33584285; PMCID: PMC7873045. 2. Du Q, Gu Z, Leneva I, Jiang H, Li R, Deng L, Yang Z. The antiviral activity of arbidol hydrochloride against herpes simplex virus type II (HSV-2) in a mouse model of vaginitis. Int Immunopharmacol. 2019 Mar;68:58-67. doi: 10.1016/j.intimp.2018.09.043. Epub 2019 Jan 3. PMID: 30612085; PMCID: PMC7106079.

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1: Galiano V, Villalaín J. The Location of the Protonated and Unprotonated Forms of Arbidol in the Membrane: A Molecular Dynamics Study. J Membr Biol. 2016 Feb 3. [Epub ahead of print] PubMed PMID: 26843065.

2: Pécheur EI, Borisevich V, Halfmann P, Morrey JD, Smee DF, Prichard M, Mire CE, Kawaoka Y, Geisbert TW, Polyak SJ. The Synthetic Antiviral Drug Arbidol Inhibits Globally Prevalent Pathogenic Viruses. J Virol. 2016 Jan 6. pii: JVI.02077-15. [Epub ahead of print] PubMed PMID: 26739045.

3: Surov AO, Manin AN, Churakov AV, Perlovich GL. New Solid Forms of the Antiviral Drug Arbidol: Crystal Structures, Thermodynamic Stability, and Solubility. Mol Pharm. 2015 Nov 2;12(11):4154-65. doi: 10.1021/acs.molpharmaceut.5b00629. Epub 2015 Oct 19. PubMed PMID: 26479207.

4: Kiselev OI, Maleev VV, Deeva ÉG, Leneva IA, Sel'kova EP, Osipova EA, Obukhov AA, Nadorov SA, Kulikova EV. [Clinical efficacy of arbidol (umifenovir) in the therapy of influenza in adults: preliminary results of the multicenter double-blind randomized placebo-controlled study ARBITR]. Ter Arkh. 2015;87(1):88-96. Russian. PubMed PMID: 25823275.

5: Di Mola A, Peduto A, La Gatta A, Delang L, Pastorino B, Neyts J, Leyssen P, de Rosa M, Filosa R. Structure-activity relationship study of arbidol derivatives as inhibitors of chikungunya virus replication. Bioorg Med Chem. 2014 Nov 1;22(21):6014-25. doi: 10.1016/j.bmc.2014.09.013. Epub 2014 Sep 16. PubMed PMID: 25282648.

6: Perfetto B, Filosa R, De Gregorio V, Peduto A, La Gatta A, de Caprariis P, Tufano MA, Donnarumma G. In vitro antiviral and immunomodulatory activity of arbidol and structurally related derivatives in herpes simplex virus type 1-infected human keratinocytes (HaCat). J Med Microbiol. 2014 Nov;63(Pt 11):1474-83. doi: 10.1099/jmm.0.076612-0. Epub 2014 Sep 3. PubMed PMID: 25187601.

7: Oestereich L, Rieger T, Neumann M, Bernreuther C, Lehmann M, Krasemann S, Wurr S, Emmerich P, de Lamballerie X, Ölschläger S, Günther S. Evaluation of antiviral efficacy of ribavirin, arbidol, and T-705 (favipiravir) in a mouse model for Crimean-Congo hemorrhagic fever. PLoS Negl Trop Dis. 2014 May 1;8(5):e2804. doi: 10.1371/journal.pntd.0002804. eCollection 2014 May. PubMed PMID: 24786461; PubMed Central PMCID: PMC4006714.

8: Blaising J, Polyak SJ, Pécheur EI. Arbidol as a broad-spectrum antiviral: an update. Antiviral Res. 2014 Jul;107:84-94. doi: 10.1016/j.antiviral.2014.04.006. Epub 2014 Apr 24. Review. PubMed PMID: 24769245.

9: Liu X, Huang T, Chen JX, Zeng J, Fan XR, Xu-Zhu, Yu ZW, Sun XY, Hong M, Sun HZ. Arbidol exhibits strong inhibition towards UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. Pharmazie. 2013 Dec;68(12):945-50. PubMed PMID: 24400440.

10: Leneva IA, Falynskova IN, Leonova EI, Fedyakina IT, Makhmudova NR, Osipova EA, Lepekha LN, Mikhailova NA, Zverev VV. [Umifenovir (Arbidol) efficacy in experimental mixed viral and bacterial pneumonia of mice]. Antibiot Khimioter. 2014;59(9-10):17-24. Russian. PubMed PMID: 25975111.

11: Nasser ZH, Swaminathan K, Müller P, Downard KM. Inhibition of influenza hemagglutinin with the antiviral inhibitor arbidol using a proteomics based approach and mass spectrometry. Antiviral Res. 2013 Nov;100(2):399-406. doi: 10.1016/j.antiviral.2013.08.021. Epub 2013 Sep 4. PubMed PMID: 24012882.

12: Severina IS, Shchegolev AIu, Medvedev AE. [Potentiation of NO-dependent activation of soluble guanylyl cyclase by 5-nitroisatin and antiviral preparatation arbidol]. Biomed Khim. 2013 May-Jun;59(3):295-304. Russian. PubMed PMID: 23987067.

13: Blaising J, Lévy PL, Polyak SJ, Stanifer M, Boulant S, Pécheur EI. Arbidol inhibits viral entry by interfering with clathrin-dependent trafficking. Antiviral Res. 2013 Oct;100(1):215-9. doi: 10.1016/j.antiviral.2013.08.008. Epub 2013 Aug 25. PubMed PMID: 23981392.

14: Liu Q, Xiong HR, Lu L, Liu YY, Luo F, Hou W, Yang ZQ. Antiviral and anti-inflammatory activity of arbidol hydrochloride in influenza A (H1N1) virus infection. Acta Pharmacol Sin. 2013 Aug;34(8):1075-83. doi: 10.1038/aps.2013.54. Epub 2013 Jun 17. PubMed PMID: 23770981; PubMed Central PMCID: PMC4003028.

15: Song JH, Fang ZZ, Zhu LL, Cao YF, Hu CM, Ge GB, Zhao DW. Glucuronidation of the broad-spectrum antiviral drug arbidol by UGT isoforms. J Pharm Pharmacol. 2013 Apr;65(4):521-7. doi: 10.1111/jphp.12014. Epub 2012 Dec 24. PubMed PMID: 23488780.

16: Sun Y, He X, Qiu F, Zhu X, Zhao M, Li-Ling J, Su X, Zhao L. Pharmacokinetics of single and multiple oral doses of arbidol in healthy Chinese volunteers. Int J Clin Pharmacol Ther. 2013 May;51(5):423-32. doi: 10.5414/CP201843. PubMed PMID: 23391367.

17: Liu X, Li H, Bi KS, Chen XH, Cai H, Cai BC. [Identification of metabolites of arbidol by ultra-high performance liquid chromatography tandem mass spectrometry]. Yao Xue Xue Bao. 2012 Nov;47(11):1521-6. Chinese. PubMed PMID: 23387087.

18: Deng P, Zhong D, Yu K, Zhang Y, Wang T, Chen X. Pharmacokinetics, metabolism, and excretion of the antiviral drug arbidol in humans. Antimicrob Agents Chemother. 2013 Apr;57(4):1743-55. doi: 10.1128/AAC.02282-12. Epub 2013 Jan 28. PubMed PMID: 23357765; PubMed Central PMCID: PMC3623363.

19: Zhang XQ, Dai JP, Cai BQ. [The in-vitro effects of arbidol hydrochloride against 2009 new influenza virus A (H1N1)]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2012 Apr;34(2):126-9. doi: 10.3881/j.issn.1000-503X.2012.02.005. Chinese. PubMed PMID: 22776596.

20: Brooks MJ, Burtseva EI, Ellery PJ, Marsh GA, Lew AM, Slepushkin AN, Crowe SM, Tannock GA. Antiviral activity of arbidol, a broad-spectrum drug for use against respiratory viruses, varies according to test conditions. J Med Virol. 2012 Jan;84(1):170-81. doi: 10.1002/jmv.22234. Epub 2011 Oct 25. PubMed PMID: 22028179.