Tavaborole

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

What is the Tavaborole?

The molecule Tavaborole presents a molecular formula of C7H6BFO2 and its IUPAC name is 5-fluoro-1-hydroxy-3H-2,1-benzoxaborole.

Tavaborole (trade name Kerydin) is a medication used to treat nail fungus. It is a member of the class of drugs known as antifungals..

Tavaborole was approved by the U.S. Food and Drug Administration (FDA) in July 2014. It is manufactured by Anacor Pharmaceuticals..

The most common side effect of tavaborole is skin irritation..

Tavaborole is applied to the affected nail once daily for 48 weeks. It is not effective for treating toenail fungus that is not associated with onychomycosis..

Tavaborole is a small molecule that inhibits the fungal enzyme squalene epoxidase. This enzyme is required for the fungus to produce ergosterol, a component of the fungal cell membrane..

In clinical trials, tavaborole was effective in treating toenail fungus in approximately 60% of patients. The most common side effects were skin irritation and nail discoloration..

Tavaborole is a safe and effective treatment for toenail fungus. It is important to follow the instructions on the package insert to ensure the best possible outcome..

3D structure

Cartesian coordinates

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

2D drawing

 

Tavaborole LFQDNHWZDQTITF-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Tavaborole

 

Molecule descriptors

 
IUPAC name5-fluoro-1-hydroxy-3H-2,1-benzoxaborole
InChI codeInChI=1S/C7H6BFO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3,10H,4H2
InChI KeyLFQDNHWZDQTITF-UHFFFAOYSA-N
SMILESOB1OCc2cc(F)ccc21

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.

  • 1,3-dihydro-5-fluoro-1-hydroxy-2,1-benzoxaborole
  • 174671-46-6
  • 2,1-Benzoxaborole, 5-fluoro-1,3-dihydro-1-hydroxy-
  • 5-FLUOROBENZO[C][1,2]OXABOROL-1(3H)-OL
  • 5-Fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
  • 5-Fluoro-1-hydroxy-2,1-benzoxaborolane
  • 5-Fluoro-1-hydroxyl-1,3-dihydrobenzo[c][1,2]oxaborole
  • 5-Fluoro-3H-benzo[c][1,2)oxaborol-1-ol
  • 5-fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol
  • 5-fluoro-1-hydroxy-3H-2,1-benzoxaborole
  • 5-fluoro-2,1-benzoxaborol-1(3H)-ol
  • 5-fluoro-3H-benzo[c][1,2]oxaborol-1-ol
  • A14999
  • AC-30887
  • AN 2690
  • AN-2690
  • AN-2690(Tavaborole)
  • AN2690
  • BCP08730
  • BDBM50370987
  • CCG-266215
  • CS-1058
  • D10169
  • DB-100333
  • DB09041
  • DS-8392
  • EX-A1086
  • F11396
  • FT-0697827
  • HSDB 8342
  • HY-10980
  • K124A4EUQ3
  • Kerydin
  • MB08883
  • MFCD10699483
  • NCGC00264110-01
  • NCGC00264110-02
  • Q21011226
  • SCH-900340
  • SY038332
  • T3775
  • Tavaborole
  • Tavaborole (AN-2690)
  • Tavaborole (USAN)
  • Z1739256284
  • p-fluorbenzoxaborole
  • s4996

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC169990691
  • UNII-K124A4EUQ3
  • AKOS006303927
  • DTXSID00169888
  • CHEMBL443052
  • CHEBI:77942
  • SCHEMBL500016

Physico-Chemical properties

IUPAC name5-fluoro-1-hydroxy-3H-2,1-benzoxaborole
Molecular formulaC7H6BFO2
Molecular weight151.931
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity39.00
LogP0.0
Topological polar surface area29.5

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.