Sitagliptin

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

What is the Sitagliptin?

The molecule Sitagliptin presents a molecular formula of C16H15F6N5O and its IUPAC name is (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one.

Sitagliptin is a medication used to treat type 2 diabetes. It works by increasing levels of two hormones, glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic peptide (GIP), which help the body to better control blood sugar levels. Sitagliptin is typically used in combination with other diabetes medications, such as metformin, and is not typically used in people with type 1 diabetes. Common side effects of sitagliptin include headache, nausea, and diarrhea..

3D structure

Cartesian coordinates

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

2D drawing

 

Sitagliptin MFFMDFFZMYYVKS-SECBINFHSA-N chemical compound 2D structure molecule svg
Sitagliptin

 

Molecule descriptors

 
IUPAC name(3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
InChI codeInChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1
InChI KeyMFFMDFFZMYYVKS-SECBINFHSA-N
SMILESN[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F

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.

  • (1R)-3-oxo-3-[3-(trifluoroethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorobenzyl)propylamine
  • (2R)-4-OXO-4-(3-(TRIFLUOROMETHYL)-5,6-DIHYDRO(1,2,4)TRIAZOLO(4,3-A)PYRAZIN-7(8H)-YL)-1-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE
  • (2R)-4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-A MINE
  • (2R)-4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE
  • (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-alpha]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
  • (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a] pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
  • (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-a
  • (3R)-3-AMINO-1-[3-(TRIFLUOROMETHYL)-5H,6H,7H,8H-[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7-YL]-4-(2,4,5-TRIFLUOROPHENYL)BUTAN-1-ONE
  • (3R)-3-Amino-1-[3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
  • (3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
  • (3R)-3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[3,4-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one hydrochloride
  • (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
  • (R)-3-AMINO-1-(3-(TRIFLUOROMETHYL)-5,6-DIHYDRO-[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL)-4-(2,4,5-TRIFLUOROPHENYL)BUTAN-1-ONE
  • (R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
  • 1,2,4-TRIAZOLO(4,3-A)PYRAZINE-7(8H)-PROPANAMINE, 5,6-DIHYDRO-.GAMMA.-OXO-3-(TRIFLUOROMETHYL)-.ALPHA.-((2,4,5-TRIFLUOROPHENYL)METHYL)-, (.ALPHA.R)-
  • 1,2,4-Triazolo(4,3-a)pyrazine, 7-((3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8-tetrahydor-3-(trifluoromethyl)-
  • 1,2,4-Triazolo[4,3-a]pyrazine,7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-
  • 1x70
  • 3-oxo-1-(2,4,5-trifluorobenzyl)-3-(3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)propylamine
  • 486460-32-6
  • 7-((3R)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)buyl)-5,6,7,8-tetrahydro-3-trifluoromethyl)-1,4-triazolo(4,3-a)
  • 7-[(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine
  • 790712-60-6
  • A14377
  • A25516
  • AB01563393_01
  • ACT02665
  • AMY6930
  • AR-270/43507782
  • AS-19118
  • BDBM11162
  • BSPBio_002262
  • CCG-268731
  • D08516
  • DB01261
  • EC 690-730-1
  • EX-A2816
  • GTPL6286
  • HMS2093F20
  • HSDB 7516
  • HY-13749
  • LEZ 763
  • LEZ-763
  • LEZ763
  • MFCD09838015
  • MK-0431
  • MK0431
  • MLS006011959
  • NCGC00178734-03
  • NCGC00178734-06
  • NCGC00178734-13
  • NSC-813215
  • NSC813215
  • Q-101366
  • Q-201711
  • Q419832
  • QFP0P1DV7Z
  • S5079
  • SBI-0206871.P001
  • SMR002546724
  • SR-05000001748
  • SR-05000001748-1
  • Sitagliptan
  • Sitagliptin
  • Sitagliptin (13)
  • Sitagliptin (Metformin,MK-0431)
  • Sitagliptin (Prop.INN)
  • Sitagliptin; MK0431
  • Tesavel
  • Triazolopiperazine Analogue 1
  • WHO 8692
  • Xelevia
  • Z1541638523
  • sitagliptina
  • sitagliptine
  • sitagliptinum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1489478
  • UNII-QFP0P1DV7Z
  • AKOS015888724
  • BRD-K19416115-001-01-2
  • BRD-K19416115-001-03-8
  • DTXSID70197572
  • CHEMBL1422
  • CHEBI:40237
  • SCHEMBL17783

Physico-Chemical properties

IUPAC name(3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
Molecular formulaC16H15F6N5O
Molecular weight407.314
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.25
LogP2.7
Topological polar surface area77.0

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.