Arbidol

Names

[ Name ]:
Arbidol

[Synonym ]:
1H-Indole-3-carboxylic acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, ethyl ester
1-methyl-2-phenylthiomethyl-3-ethoxycarbonyl-4-dimethylaminomethyl-5-hydroxy-6-bromindole
ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylate
Ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate
Umifenovir
6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester
6-bromo-4-dimethylaminomethyl-3-ethoxycarbonyl-5-hydroxy-1-methyl-2-phenylthiomethylindole
Arbidol
1-methyl-2-phenylthiomethyl-3-carbethoxy-4-dimethylaminomethyl-5-oxy-6-bromoindole
HMS589B06

Biological Activity

[Description]:

Umifenovir is a potent, orally active broad-spectrum antiviral agent with activity against a number of enveloped and non-enveloped viruses. Umifenovir is used as an anti-influenza virus agent. Umifenovir could effectively inhibit the fusion of virus with host cells[1][2]. Umifenovir is an efficient inhibitor of SARS-CoV-2 in vitro[2]. Umifenovir shows anti-inflammatory activity[3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> SARS-CoV

[In Vitro]

Umifenovir exhibits a wide range and potent antiviral activity against a number of viruses including influenza viruses A, B and C, respiratory syncytial virus, SARS-CoV, adenovirus, parainfluenza type 5, poliovirus 1, rhinovirus 14, coxsackievirus B5, hantaan virus, Chikungunya virus, HBV and HCV[1].

[In Vivo]

Umifenovir (25 and 45 mg/ml; p.o.;) shows a survival benefit to mice suffering from influenza infection[3]. Animal Model: BALB/c mice (6–8 weeks old), mice were intranasally (i.n.) inoculated with 2 times the 50% mouse lethal dose (MLD50) of A/ Guangdong/GIRD07/09 (H1N1) (104.5TCID50/mL) in a volume of 20mL[3]. Dosage: 1.25 mg/mL (25 mg/kg/day) and 2.25 mg/mL (45 mg/kg/day) in a total volume of 500mL at one day pre-infection and 3 days post-infection (dpi) Administration: Oral administration Result: Increased the survival rate, inhibited the decrease of body weight at 45 mg/mL and inhibited the increase of mice lung index at 25 mg/mL and 45 mg/mL comparing to virus group.

[References]

[1]. Julie Blaising, et al. 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.

[2]. Irina Leneva, et al. Antiviral Activity of Umifenovir In Vitro against a Broad Spectrum of Coronaviruses, Including the Novel SARS-CoV-2 Virus. Viruses. 2021 Aug 23;13(8):1665.

[3]. Yutao Wang, et al. Inhibition of the infectivity and inflammatory response of influenza virus by Arbidol hydrochloride in vitro and in vivo (mice and ferret). Biomed Pharmacother. 2017 Jul;91:393-401.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
591.8±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₂₅BrN₂O₃S

[ Molecular Weight ]:
477.41

[ Flash Point ]:
311.7±30.1 °C

[ Exact Mass ]:
476.076904

[ PSA ]:
80.00000

[ LogP ]:
4.64

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.620

Synthetic Route

Click to get detail synthetic route

Related Compounds

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