(R)-Fluoxetine

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

What is the (R)-Fluoxetine?

The molecule (R)-Fluoxetine presents a molecular formula of C22H26N2O4 and its IUPAC name is (3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine.

R-Fluoxetine is a molecule that is used in the treatment of depression and other mental disorders. It is a selective serotonin reuptake inhibitor (SSRI), which means it increases the level of serotonin in the brain by blocking its reuptake into the neurons. This action is thought to be the mechanism by which SSRIs alleviate depression..

R-Fluoxetine was first synthesized in 1974 by Belgian chemist Leo Sternbach while working for the pharmaceutical company Hoffman-La Roche. It was originally patented as a treatment for depression in 1986 and was approved by the US Food and Drug Administration (FDA) for that use in 1987. It is now also approved for the treatment of obsessive-compulsive disorder (OCD), bulimia nervosa, and panic disorder..

R-Fluoxetine exists as a generic drug and is marketed under a variety of brand names, including Prozac and Sarafem. It is typically taken orally in the form of a capsule or tablet, although it can also be administered as an oral solution or suspension. The usual starting dose is 20 mg per day, which may be increased to a maximum of 80 mg per day if needed..

R-Fluoxetine is generally well-tolerated, with the most common side effects being nausea, headache, dry mouth, and insomnia. It can also cause sexual side effects, such as decreased libido and anorgasmia. Rare but serious side effects include serotonin syndrome and suicidal thoughts or behaviors..

R-Fluoxetine should not be taken with monoamine oxidase inhibitors (MAOIs) or tricyclic antidepressants, as this can lead to serious and potentially life-threatening side effects. It is also important to tell your doctor if you are taking any other medications, as R-Fluoxetine may interact with them..

If you are considering taking R-Fluoxetine for the treatment of depression or another mental disorder, talk to your doctor about the potential risks and benefits..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Fluoxetine RUJBDQSFYCKFAA-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(R)-Fluoxetine

 

Molecule descriptors

 
IUPAC name(3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
InChI codeInChI=1S/C22H26N2O4/c1-7-15-13(2)23-24-22(14-8-9-18(25-3)19(10-14)26-4)17-12-21(28-6)20(27-5)11-16(15)17/h8-12,15H,7H2,1-6H3/t15-/m1/s1
InChI KeyRUJBDQSFYCKFAA-OAHLLOKOSA-N
SMILESCC[C@@H]1C(C)=NN=C(c2ccc(OC)c(OC)c2)c2cc(OC)c(OC)cc21

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.

  • (+)-fluoxetine
  • (+/-)-Fluoxetine
  • (3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine
  • (3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
  • (R)-(+)-fluoxetine
  • (R)-(+/-)-Fluoxetine
  • (R)-Fluoxetine
  • (R)-N-Methyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine
  • (R)-N-methyl-3-(4-trifluoromethylphenoxy)-3-phenylpropylamine
  • (R)-N-methyl-3-(4-trifluoromethylphenyloxy)-3-(phenyl)propylamine
  • (R)-N-methyl-3-phenyl-3-[(alpha,alpha,alpha-trifluoro-p-tolyl)oxy]propylamine
  • (R)-N-methyl-gamma-(4-trifluoromethylphenoxy)-3-phenylpropylamine
  • (R)-Prozac
  • 100568-03-4
  • 247F095
  • A830402
  • BDBM50136166
  • BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(4-(TRIFLUOROMETHYL)PHENOXY)-, (.GAMMA.R)-
  • BIDD:GT0614
  • Benzenepropanamine, N-methyl-gamma-(4-(trifluoromethyl)phenoxy)-, (gammaR)-
  • Benzenepropanamine,?N-methyl-.gamma.-[4-(trifluoromethyl)phenoxy]-, (.gamma.R)-
  • CCG-204576
  • DB08472
  • F279341RUQ
  • Fluoxetine, (R)-
  • Lopac0_000485
  • Methyl-[(R)-3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
  • Methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]-amine
  • NCGC00162170-01
  • PDSP1_001304
  • PDSP2_001288
  • Q27097676
  • R-FLUOXETINE
  • RFX

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530638
  • UNII-F279341RUQ
  • AKOS015914491
  • DTXSID10872290
  • CHEMBL153036
  • CHEBI:86991
  • SCHEMBL1200433

Physico-Chemical properties

IUPAC name(3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
Molecular formulaC22H26N2O4
Molecular weight382.453
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity117.97
LogP3.3
Topological polar surface area61.6

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.