(S)-butoconazole

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

What is the (S)-butoconazole?

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

Butoconazole is a synthetic antifungal drug belonging to the triazole class. It is used to treat fungal infections of the vagina, such as candidiasis (yeast infection). Butoconazole is sold under the brand names Femstat, Gynazole-1, and Mycelex-3..

Butoconazole is a white to off-white crystalline powder with a melting point of 122-124°C. It is soluble in ethanol, methanol, and chloroform, and slightly soluble in water..

The mechanism of action of butoconazole is not fully understood, but it is thought to work by inhibiting the synthesis of ergosterol, a key component of the fungal cell membrane. This action leads to the death of the fungus..

Butoconazole exists as a cream, suppository, and troche. It is applied to the affected area(s) of the vagina and surrounding skin once or twice a day for 3-7 days. Butoconazole should not be used during pregnancy unless the potential benefit justifies the potential risk to the fetus..

Butoconazole is generally well tolerated. The most common side effects are burning, itching, and irritation of the skin. Butoconazole should not be used by people with a history of hypersensitivity to triazoles..

Butoconazole is a safe and effective treatment for vaginal candidiasis. It is important to finish the entire course of therapy to prevent the infection from coming back..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-butoconazole SWLMUYACZKCSHZ-INIZCTEOSA-N chemical compound 2D structure molecule svg
(S)-butoconazole

 

Molecule descriptors

 
IUPAC name1-[(2S)-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-/m0/s1
InChI KeySWLMUYACZKCSHZ-INIZCTEOSA-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.

  • (2R)-1-[2-(2,6-Dichlorophenylthio)-4-(4-chlorophenyl)butyl]-1H-imidazole nitrate
  • (S)-butoconazole
  • 1-[(2S)-4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole
  • 1-[(S)-4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole
  • 1-{(2S)-4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1H-imidazole
  • 151909-74-9
  • 1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (S)-
  • 7LKA6W37RP
  • BIDD:GT0690
  • Butoconazole nitrate enantiomer
  • Butoconazole, (S)-
  • Q27126597
  • SWLMUYACZKCSHZ-INIZCTEOSA-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530973
  • UNII-7LKA6W37RP
  • CHEBI:59288
  • SCHEMBL44239

Physico-Chemical properties

IUPAC name1-[(2S)-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.