(S)-Bifonazole

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

What is the (S)-Bifonazole?

The molecule (S)-Bifonazole presents a molecular formula of C22H18N2 and its IUPAC name is 1-[(S)-phenyl-(4-phenylphenyl)methyl]imidazole.

Bifonazole is an antifungal medication of the imidazole class. It is used to treat fungal infections such as athlete's foot, jock itch, and ringworm. It is also used to treat candidiasis (yeast infection). Bifonazole exists as a cream, powder, and spray..

Bifonazole was patented in 1981 and approved for medical use in 1987. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Bifonazole exists as a generic medication..

The mechanism of action of bifonazole is not well understood. It is thought to work by preventing the fungus from growing and multiplying..

Bifonazole is well tolerated. The most common side effects are itching and burning..

Bifonazole is a safe and effective medication for the treatment of fungal infections. It is important to follow the directions on the package and to use the medication for the full course of treatment..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-Bifonazole OCAPBUJLXMYKEJ-QFIPXVFZSA-N chemical compound 2D structure molecule svg
(S)-Bifonazole

 

Molecule descriptors

 
IUPAC name1-[(S)-phenyl-(4-phenylphenyl)methyl]imidazole
InChI codeInChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H/t22-/m0/s1
InChI KeyOCAPBUJLXMYKEJ-QFIPXVFZSA-N
SMILESc1ccc(-c2ccc([C@H](c3ccccc3)n3ccnc3)cc2)cc1

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.

  • (S)-(+)-bifonazole
  • (S)-Bifonazole
  • 1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole
  • 1-[(S)-biphenyl-4-yl(phenyl)methyl]-1H-imidazole
  • 1H-Imidazole, 1-((S)-(1,1'-biphenyl)-4-ylphenylmethyl)-
  • 5H4GD68KZG
  • 91487-86-4
  • Bifonazole, (-)-
  • Bifonazole, (S)-
  • NCGC00018254-01
  • NCGC00018254-06
  • Q27147915

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3812958
  • UNII-5H4GD68KZG
  • CHEBI:78694
  • SCHEMBL1551534

Physico-Chemical properties

IUPAC name1-[(S)-phenyl-(4-phenylphenyl)methyl]imidazole
Molecular formulaC22H18N2
Molecular weight310.392
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.90
LogP5.2
Topological polar surface area17.8

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.