(R)-butaconazole

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

What is the (R)-butaconazole?

The molecule (R)-butaconazole presents a molecular formula of C19H17Cl3N2S and its IUPAC name is 1-[(2R)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole.

Butaconazole is an antifungal medication used to treat fungal infections of the skin. It is a member of the azole class of drugs and was approved by the U.S. Food and Drug Administration (FDA) in 1999. Butaconazole exists as a cream, gel, and solution and is applied to the affected area two or three times a day. Common side effects include itching, redness, and burning. Butaconazole is in the pregnancy category C, meaning that it may be harmful to a developing fetus..

Butaconazole is an antifungal medication used to treat fungal infections of the skin. It is a member of the azole class of drugs and was approved by the U.S. Food and Drug Administration (FDA) in 1999. Butaconazole exists as a cream, gel, and solution and is applied to the affected area two or three times a day. Common side effects include itching, redness, and burning. Butaconazole is in the pregnancy category C, meaning that it may be harmful to a developing fetus..

Butaconazole is an antifungal medication used to treat fungal infections of the skin. It is a member of the azole class of drugs and was approved by the U.S. Food and Drug Administration (FDA) in 1999. Butaconazole exists as a cream, gel, and solution and is applied to the affected area two or three times a day. Common side effects include itching, redness, and burning. Butaconazole is in the pregnancy category C, meaning that it may be harmful to a developing fetus..

Butaconazole is an antifungal medication used to treat fungal infections of the skin. It is a member of the azole class of drugs and was approved by the U.S. Food and Drug Administration (FDA) in 1999. Butaconazole exists as a cream, gel, and solution and is applied to the affected area two or three times a day. Common side effects include itching, redness, and burning. Butaconazole is in the pregnancy category C, meaning that it may be harmful to a developing fetus..

Butaconazole is an antifungal medication used to treat fungal infections of the skin. It is a member of the azole class of drugs and was approved by the U.S. Food and Drug Administration (FDA) in 1999. Butaconazole exists as a cream, gel, and solution and is applied to the affected area two or three times a day. Common side effects include itching, redness, and burning. Butaconazole is in the pregnancy category C, meaning that it may be harmful to a developing fetus..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-butaconazole SWLMUYACZKCSHZ-MRXNPFEDSA-N chemical compound 2D structure molecule svg
(R)-butaconazole

 

Molecule descriptors

 
IUPAC name1-[(2R)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
InChI codeInChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2/t16-/m1/s1
InChI KeySWLMUYACZKCSHZ-MRXNPFEDSA-N
SMILESClc1ccc(CC[C@H](Cn2ccnc2)Sc2c(Cl)cccc2Cl)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.

  • (2S)-1-[2-(2,6-Dichlorophenylthio)-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate
  • (R)-butaconazole
  • 0U3014I7B2
  • 1-[(2R)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole
  • 1-[(R)-4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole
  • 1-{(2R)-4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1H-imidazole
  • 151909-76-1
  • 1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (R)-
  • Butoconazole nitrate enantiomer
  • Butoconazole, (R)-
  • NCGC00016812-01
  • Q27126596

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530974
  • CAS-32872-77-1
  • UNII-0U3014I7B2
  • CHEMBL1317950
  • CHEBI:59287
  • SCHEMBL44238

Physico-Chemical properties

IUPAC name1-[(2R)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
Molecular formulaC19H17Cl3N2S
Molecular weight411.776
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity108.67
LogP6.6
Topological polar surface area43.1

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.