Pitavastatin

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

What is the Pitavastatin?

The molecule Pitavastatin presents a molecular formula of C25H24FNO4 and its IUPAC name is (E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid.

Pitavastatin is a member of the statin class of lipid-lowering medications. It is marketed as Livalo and Pitava. (1).

Pitavastatin is a prodrug that is metabolized in the liver to its active form, pitavastatin lactone. (2) The mechanism of action of pitavastatin is to inhibit HMG-CoA reductase, an enzyme that is responsible for the production of cholesterol in the liver. (3).

Pitavastatin has been shown to be effective in reducing LDL cholesterol, total cholesterol, and triglycerides. (4) It also increases HDL cholesterol. (5).

Pitavastatin is generally well-tolerated. The most common side effects are mild and include headache, diarrhea, and nausea. (6).

Pitavastatin is a safe and effective lipid-lowering medication that can be used to treat patients with high cholesterol..

3D structure

Cartesian coordinates

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

2D drawing

 

Pitavastatin VGYFMXBACGZSIL-MCBHFWOFSA-N chemical compound 2D structure molecule svg
Pitavastatin

 

Molecule descriptors

 
IUPAC name(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
InChI codeInChI=1S/C25H24FNO4/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31)/b12-11+/t18-,19-/m1/s1
InChI KeyVGYFMXBACGZSIL-MCBHFWOFSA-N
SMILESO=C(O)C[C@H](O)C[C@H](O)/C=C/c1c(C2CC2)nc2ccccc2c1-c1ccc(F)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.

  • (+)-(3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoic acid
  • (3R,5S)-3,5-Dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-6-heptenoic acid
  • (3R,5S,6E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid
  • (3R,5S,6E)-7-(2-Cyclopropyl-4-(p-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoic acid
  • (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy hept-6-enoic acid
  • (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
  • (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid
  • (3r,5s,6e)-7-[2-cyclopropyl-4-(p-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid
  • (E)-(3R,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid
  • (E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
  • (e)-(3r,5s)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6enoic acid
  • 121659-03-8
  • 147511-69-1
  • 6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, (3R,5S,6E)-
  • 6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, (S-(R*,S*-(E)))-
  • 6-Heptenoic acid, 7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-, (3R,5S,6E)-
  • AM84440
  • BDBM86707
  • CAS_147511-69-1
  • DB08860
  • E-(3R,5S)-7-[2-Cyclopropyl-4-(4fluoro-phenyl)quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid
  • GTPL3035
  • HSDB 8367
  • HY-B0144A
  • Itavastatin
  • Itavastin
  • Livalo
  • M5681Q5F9P
  • MLS006010096
  • NIKITA
  • NK 104
  • NK-104
  • NSC 760423
  • NSC-760423
  • P 872441
  • P-872441
  • Pitavastatin
  • Pitavastatin calcium
  • Q412677
  • SMR003965244
  • pitavastatia
  • pitavastatine
  • pitavastatinum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1534965
  • UNII-M5681Q5F9P
  • AKOS005145916
  • BRD-K75958547-001-01-2
  • DTXSID1048384
  • CHEMBL1201753
  • CHEBI:32020
  • SCHEMBL3369
  • SCHEMBL464781

Physico-Chemical properties

IUPAC name(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
Molecular formulaC25H24FNO4
Molecular weight421.461
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity117.82
LogP4.5
Topological polar surface area90.7

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.