Arbidol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Arbidol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Arbidol?

The molecule Arbidol presents a molecular formula of C22H25BrN2O3S and its IUPAC name is ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate.

Arbidol is a synthetic antiviral drug that is commonly used to treat influenza and other respiratory infections in Russia and other countries. It is also known by its chemical name, umifenovir, and is sold under a variety of brand names, including Arpeflu, Arpetad, and Hainan..

Arbidol is classified as an adamantane derivative, which means that it is structurally related to a group of compounds that have been shown to be effective against influenza viruses. Arbidol is believed to work by inhibiting the replication of influenza viruses and by stimulating the immune system to fight off the infection..

Arbidol has been shown to be effective in the treatment and prevention of influenza, including strains that are resistant to other antiviral drugs such as oseltamivir (Tamiflu). It has also been shown to be effective against other respiratory viruses, including respiratory syncytial virus (RSV) and parainfluenza virus..

In addition to its antiviral properties, arbidol has been shown to have a number of other potential health benefits. It has been shown to have antioxidant, anti-inflammatory, and immune-modulating effects, which may be helpful in the treatment of a variety of conditions..

Despite its potential benefits, arbidol has not been approved for use in the United States and is not widely available in other countries. It is not currently recommended as a first-line treatment for influenza in most countries, and its effectiveness and safety have been the subject of debate and controversy..

Summary

From all the above, this molecule is a synthetic antiviral drug that is commonly used to treat influenza and other respiratory infections in Russia and other countries. It is classified as an adamantane derivative and is believed to work by inhibiting the replication of influenza viruses and by stimulating the immune system. Arbidol has been shown to be effective in the treatment and prevention of influenza and other respiratory viruses, and it has a number of other potential health benefits. However, it is not widely available in many countries and its effectiveness and safety are controversial..

3D structure

Cartesian coordinates

Geometry of Arbidol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Arbidol KCFYEAOKVJSACF-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Arbidol

 

Molecule descriptors

 
IUPAC nameethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
InChI codeInChI=1S/C22H25BrN2O3S/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
InChI KeyKCFYEAOKVJSACF-UHFFFAOYSA-N
SMILESCCOC(=O)c1c(CSc2ccccc2)n(C)c2cc(Br)c(O)c(CN(C)C)c12

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-METHYL-2-((PHENYLTHIO)METHYL)-3-CARBETHOXY-4-((DIMETHYLAMINO)METHYL)-5-HYDROXY-6-BROMINDOLE
  • 131707-25-0
  • 1H-Indole-3-carboxylic acid, 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-, ethyl ester
  • 1H-Indole-3-carboxylic acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, ethyl ester
  • 1H-indole-3-carboxylic acid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, ethyl ester, hydrochloride
  • 5674-91-9
  • 6-Bromo-4-dimethylaminomethyl-5-hydroxy-1-methyl-2-phenylsulfanylmethyl-1H-indole-3-carboxylic acid ethyl ester
  • 6-Bromo-4-dimethylaminomethyl-5-hydroxy-1-methyl-2-phenylsulfanylmethyl-1H-indole-3-carboxylic acid ethyl ester
  • 6-Bromo-5-hydroxy-4-methylaminomethyl-1-methyl-2-benzenesulfenylmethylindole-3-ethyl carboxylate
  • 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-3-indolecarboxylic acid ethyl ester
  • 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]indole-3-carboxylic acid ethyl ester
  • 75U
  • 93M09WW4RU
  • A888382
  • AB00644670_06
  • AR-1I9514
  • AT13213
  • Arbidol
  • Arbidol base
  • Arbidol; Umifenovir
  • BCP04187
  • BDBM83797
  • CS-0003625
  • ChemDiv1_000732
  • D10558
  • DB13609
  • DT-0014
  • ETHYL 6-BROMO-4-((DIMETHYLAMINO)METHYL)-5-HYDROXY-1-METHYL-2-((PHENYLSULFANYL)METHYL)-1H-INDOLE-3-CARBOXYLATE
  • EX-A3050
  • Ethyl 6-bromo-5-hydroxy-1-methyl-4-((dimethylamino)methyl)-2-[(phenylthio)methyl]-1H-indole-3-carboxylate
  • GTPL11089
  • HMS2760J21
  • HMS589B06
  • HY-14904
  • MFCD01326495
  • MLS000777586
  • MLS006011808
  • NCGC00246387-01
  • NCGC00246387-02
  • NCGC00246387-06
  • NCGC00246387-09
  • Oprea1_384852
  • Oprea1_482224
  • Q27271599
  • SMR000413980
  • STK021887
  • Umifenovir (INN)
  • cid_131411
  • ethyl 6-bromanyl-4-[(dimethylamino)methyl]-1-methyl-5-oxidanyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
  • ethyl 6-bromo-4-((dimethylamino)methyl)-5-hydroxy-1-methyl-2-((phenylthio)methyl)-1H-indole-3-carboxylate
  • ethyl 6-bromo-4-(dimethylaminomethyl)-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
  • ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
  • ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate
  • ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxilate
  • umifenovir

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC19907652
  • UNII-93M09WW4RU
  • AKOS001485435
  • ALBB-028966
  • DTXSID60895015
  • CHEMBL1214598
  • CHEBI:134730
  • SCHEMBL1068701

Physico-Chemical properties

IUPAC nameethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
Molecular formulaC22H25BrN2O3S
Molecular weight477.414
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity122.69
LogP5.2
Topological polar surface area80.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.