Arbidol

Base Information

• Chemical Name: Arbidol
• CAS No.: 131707-25-0
• Molecular Formula: C22H25BrN2O3S
• Molecular Weight: 477.422
• European Community (EC) Number: 814-571-6,921-763-4
• UNII: 93M09WW4RU
• DSSTox Substance ID: DTXSID60895015
• Nikkaji Number: J439.246I
• Wikipedia: Umifenovir
• Wikidata: Q27271599
• NCI Thesaurus Code: C152799
• Metabolomics Workbench ID: 144547
• ChEMBL ID: CHEMBL1214598
• Mol file: 131707-25-0.mol

Synonyms:1-methyl-2-((phenylthio)methyl)-3-carbethoxy-4-((dimethylamino)methyl)-5-hydroxy-6-bromoindole;1H-indole-3-carboxylic acid, 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-, ethyl ester;arbidol;arbidole;umifenovir;umifenovir hydrochloride;umifenovir hydrochloride monohydrate;umifenovir sulfoxide

Chemical Property of Arbidol

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 1.34E-14mmHg at 25°C
• Refractive Index: 1.619
• Boiling Point: 591.776 °C at 760 mmHg
• PKA: 6.02±0.50(Predicted)
• Flash Point: 311.695 °C
• PSA: 80.00000
• Density: 1.375 g/cm³
• LogP: 5.17700
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 476.07693
• Heavy Atom Count: 29
• Complexity: 546

Purity/Quality:

98%,99%, ^*data from raw suppliers

Umifenovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N(C2=CC(=C(C(=C21)CN(C)C)O)Br)C)CSC3=CC=CC=C3
• Recent ClinicalTrials: The Efficacy and Safety of Arbidol in Reducing the Frequency of AECOPD.
• Description: Arbidol, or umifenovir, an indole-derivative with broad-spectrum activity against both enveloped and non-enveloped viruses,was initially approved in China and Russia for the treatment of influenza A and B.Arbidol is believed to block the entry of influenza virus (A and B) into the host cells by increasing the stability of the hemagglutinin (HA) and hampering low pH reorganizations necessary for fusion machinery of hemagglutinin with the membrane.Arbidol could interfere with advanced stages of the viral life cycle, in that it is capable of interacting with both viral proteins and lipids.Regarding its structure, the presence of amine in position 4 and the hydroxyl moiety in position 5 is crucial for its antiviral activity. It is reported that 40% of the drug could be excreted unchanged after the administration while its half-life is between 17 and 21h.
• Uses: Umifenovir is an intermediate in synthesizing Arbidol Sulfoxide (A766005), a metabolite of Arbidol (A766000) which is a medicinal agent for treating viral infections.
• Clinical Use: Arbidol in Treatment of covID-19Although,arbidol is not approved by US-FDA for the treatment of cOVID-19,some pre-clinical and clinical studies have reported that it may be a very efficacious therapeutic molecule for COVID-19 (Deng et al.,2020; Wang et al.,2020).Arbidol has been included in the latest version of the guidelines issued by the National Health Commission (NHC) of the people's republic of China for the prevention, diagnosis, and treatment of novel coronavirus induced pneumonia at the recommended dose of 200 mg, 3 times/day for 10 days for adults (National Health Commission,China).An in-vitro study claimed that arbidol is effective against COVID-19 at the concentration range of 10-30 uM (News: Abidol and darunavir can effectively inhibit corona virus (2020). A retrospective study conducted by Deng and colleagues reported that patients who received oral arbidol plus lopinavir/ritonavir showed improvement in clinical symptoms and reduced viral load as a compared to the patients who received lopinavir/ritonavir alone (Deng et al.，2020).A randomized multi-centre controlled clinical trial of arbidol in the patients with cOVID-19 is currently running in China (ChiCTR2000029573).Besides this, one more study was conducted on 69 patients of COVID-19.In this study, it was reported that the administration of arbidol at the dose of 0.4 g,TID for 9 days improves the discharging rate from the hospital and also decreases the mortality rate of patients (Wang et al.，2020). In addition，another study also reported that arbidol is more superior to the combination therapy of lopinavir/ritonavir (Zhu et al.，2020).Arbidol: a broad-spectrum antiviral compound that blocks viral fusionArbidol: A potential antiviral drug for the treatment of SARS-CoV-2 by blocking trimerization of the spike glycoprotein

Technology Process of Arbidol

There total 10 articles about Arbidol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.1%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimethyl amine (124-40-3) + 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester (131707-24-9) → arbidol (131707-25-0)

Guidance literature:

With acetic acid; In water; at 65 - 75 ℃; for 0.5h;

DOI:10.1007/BF00772858

Reference yield: 70.0%

bis-(dimethylamino)methane (51-80-9) + 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester (131707-24-9) → arbidol (131707-25-0)

Guidance literature:

In 1,4-dioxane; for 3h; Heating;

DOI:10.1007/BF00772858

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester (131707-24-9) → arbidol (131707-25-0)

Guidance literature:

With potassium hydroxide; acetic acid; dimethyl amine;

upstream raw materials:

bis-(dimethylamino)methane

6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester

formaldehyd

dimethyl amine

Downstream raw materials:

Arbidol hydrochloride

6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester

Refernces

• 1、 -. "ARBIDOL ANALOGS WITH IMPROVED INFLUENZA HEMAGGLUTININ POTENCY". Page/Page column 9-10; 12. . Retrieved 2018/07/05.
• 2、 Trofimov, F.A.,Tsyshkova, N.G.,Zotova, S.A.,Grinev, A.N.. "SYNTHESIS OF A NEW ANTIVIRAL AGENT, ARBIDOLE". . p. 75 - 76. Retrieved 2007/10/02.