Arbidol Hydrochloride

Base Information

• Chemical Name: Arbidol Hydrochloride
• CAS No.: 131707-23-8
• Molecular Formula: C22H26BrClN2O3S
• Molecular Weight: 513.883
• Hs Code.: 2933990090
• European Community (EC) Number: 680-680-9
• UNII: 8CXV4OU367
• Wikidata: Q4475505
• ChEMBL ID: CHEMBL5179853
• Mol file: 131707-23-8.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 Hydrochloride

Chemical Property:

• Appearance/Colour: White or off-white crystalline powder
• Vapor Pressure: 1.34E-14mmHg at 25°C
• Melting Point: 133-137?C
• Boiling Point: 591.8 ºC at 760 mmHg
• Flash Point: 311.7 ºC
• PSA: 80.00000
• LogP: 5.97900
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO: soluble20mg/mL protein, clear
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 512.05360
• Heavy Atom Count: 30
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Arbidol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

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.Cl
• Description: Umifenovir is a broad-spectrum antiviral agent. It inhibits the replication of H5N1 influenza (IC50 = 30 μg/ml) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in vitro (IC50 = 3.537 μM). Umifenovir inhibits entry of hepatitis C virus (HCV) pseudoparticles in Huh7 cells (IC50 = 6 μg/ml) and inhibits Zika virus protein synthesis in Vero cells. In vivo, umifenovir (45 mg/kg) reduces the formation of influenza-induced lung lesions in ferrets.
• Uses: Arbidol is an antiviral treatment for influenza infection. Arbidol hydrochloride (ARB) is a small monocular compound. It is used to prevent severe pneumonia and virus-associated cytokine dysregulation induced by influenza viruses (IFV). ARB also possesses some immunomodulatory properties, including the effects of interferon induction and macrophage activation.Arbidol is a broad-spectrum antiviral that has demonstrated activity against a number of enveloped and non-enveloped viruses, and is used clinically to treat influenza. Arbidol inhibits viral entry into host cell and stimulates immune response. Arbidol inhibits fusion between the viral capsid and the cell membrane of the target cell, thus preventing viral entry.

Technology Process of Arbidol Hydrochloride

There total 10 articles about Arbidol Hydrochloride 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: 85.6%

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 hydrochloride (131707-23-8)

Guidance literature:

formaldehyd; dimethyl amine; 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester; With aminosulfonic acid; In water; at 30 - 40 ℃; for 3h; Cooling with ice;

With hydrogenchloride; In water; acetone; at 60 ℃; pH=1;

Reference yield: 75.0%

arbidol (131707-25-0) → Arbidol hydrochloride (131707-23-8)

Guidance literature:

With hydrogenchloride; In acetone; for 0.5h; Reflux;

Reference yield:

1,2-dimethyl-5-acetoxy-1H-indole-3-carboxylic acid ethyl ester (40945-79-7) → Arbidol hydrochloride (131707-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux

2.1: sodium hydroxide / methanol / 2 h

2.2: 3 h

3.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice

3.2: 60 °C / pH 1

With aminosulfonic acid; bromine; sodium hydroxide; dibenzoyl peroxide; In methanol; chloroform; water;

upstream raw materials:

ethyl 5-acetyloxy-2-methyl-1H-indole-3-carboxylate

1,2-dimethyl-5-acetoxy-1H-indole-3-carboxylic acid ethyl ester

4-nitro-phenol

formaldehyd

Refernces

• 1、 -. "Preparation method of arbidol hydrochloride". . . Retrieved 2017/02/09.