Tafluprost

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

What is the Tafluprost?

The molecule Tafluprost presents a molecular formula of C25H34F2O5 and its IUPAC name is propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate.

Tafluprost is a synthetic prostaglandin analog and a selective agonist of the prostaglandin F2-alpha receptor. It is used as an ocular hypotensive agent in the treatment of glaucoma and ocular hypertension..

3D structure

Cartesian coordinates

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

2D drawing

 

Tafluprost WSNODXPBBALQOF-VEJSHDCNSA-N chemical compound 2D structure molecule svg
Tafluprost

 

Molecule descriptors

 
IUPAC namepropan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
InChI codeInChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1
InChI KeyWSNODXPBBALQOF-VEJSHDCNSA-N
SMILESCC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/C(F)(F)COc1ccccc1

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.

  • (Z)-isopropyl 7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxy cyclopentyl)hept-5-enoate
  • (Z)-isopropyl 7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
  • (Z)-isopropyl7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
  • 1-Methylethyl (5-Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoate
  • 1-methylethyl (5Z)-7-((1R,2R, 3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy -1-butenyl-3,5-dihydroxycyclopentyl)-5-heptenoate
  • 1-methylethyl (5Z)-7-{(1R,2R,3R,5S)-2-((1E)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5- dihydroxycyclopentyl}hept-5-enoate
  • 1O6WQ6T7G3
  • 209860-87-7
  • 5-Heptenoic acid, 7-((1R,2R,3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl)-3,5- dihydroxycyclopentyl)-, 1-methylethyl ester, (5Z)-
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-
  • 860T877
  • AFP-168
  • AS-75193
  • CCG-269257
  • D06274
  • DB08819
  • DE-085
  • DE-118
  • EX-A564
  • GTPL7451
  • HMS3649F04
  • HY-B0600
  • ISOPROPYL (5Z)-7-((1R,2R,3R,5S)-2-((1E)-3,3-DIFLUORO-4-PHENOXYBUT-1-ENYL)-3,5-DIHYDROXYCYCLOPENTYL)HEPT-5-ENOATE
  • Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-((1E)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl}hept-5-enoate
  • J-502635
  • MK-2452
  • MK2452
  • MK2452AFP-168
  • Q2139543
  • SR-01000946707
  • SR-01000946707-1
  • Saflutan
  • Taflotan
  • Tafluprost
  • Tafluprost (JAN/USAN/INN)
  • Tapros
  • Zioptan
  • isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate
  • propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate
  • propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-(phenoxy)but-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
  • propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
  • s4851

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13912394
  • UNII-1O6WQ6T7G3
  • AKOS025294885
  • DTXSID401021504
  • CHEMBL1963683
  • CHEBI:66899
  • SCHEMBL1286148

Physico-Chemical properties

IUPAC namepropan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
Molecular formulaC25H34F2O5
Molecular weight452.531
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity120.15
LogP4.7
Topological polar surface area76.0

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.