715

(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

Created:2004-08-16
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count1
Bond Count45
Aromatic Bond Count11
2D diagram of 715
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Chemical Component Summary

Name(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
SynonymsSitagliptin
Systematic Name (OpenEye OEToolkits)(3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
FormulaC16 H15 F6 N5 O
Molecular Weight407.314
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04Fc1cc(c(F)cc1F)CC(N)CC(=O)N3Cc2nnc(n2CC3)C(F)(F)F
SMILESCACTVS3.341N[CH](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc3cc(F)c(F)cc3F
SMILESOpenEye OEToolkits1.5.0c1c(c(cc(c1F)F)F)CC(CC(=O)N2CCn3c(nnc3C(F)(F)F)C2)N
Canonical SMILESCACTVS3.341 N[C@@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc3cc(F)c(F)cc3F
Canonical SMILESOpenEye OEToolkits1.5.0 c1c(c(cc(c1F)F)F)C[C@H](CC(=O)N2CCn3c(nnc3C(F)(F)F)C2)N
InChIInChI1.03 InChI=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
InChIKeyInChI1.03 MFFMDFFZMYYVKS-SECBINFHSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB01261 
NameSitagliptin
Groups
  • approved
  • investigational
DescriptionSitagliptin is an oral dipeptidyl peptidase-4 (DPP-4) inhibitor used in conjunction with diet and exercise to improve glycemic control in patients with type 2 diabetes mellitus[FDA label,A2260,A2255,A2256]. The effect of this medication leads to glucose dependent increases in insulin and decreases in glucagon to improve control of blood sugar[FDA label,A2255]. Sitagliptin was granted FDA approval on October 16, 2006[L6061].
Synonyms
  • Sitagliptin tartrate hemihydrate
  • Sitagliptin malate
  • Sitagliptin phosphate
  • Sitagliptin fumarate
  • Sitagliptin hydrochloride monohydrate
Brand Names
  • Xelevia
  • Sitagliptin and Metformin Hydrochloride
  • Sitagliptin Sun
  • Sitagliptin-metformin
  • Auro-sitagliptin
IndicationSitagliptin is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. It is not used to treat type 1 diabetes or patients with a history of pancreatitis.[L41220] It is also used in combination with [metformin] [L41215] or [ertugliflozin].[L41225]
Categories
  • Agents causing angioedema
  • Alimentary Tract and Metabolism
  • Blood Glucose Lowering Agents
  • Cytochrome P-450 CYP2C8 Substrates
  • Cytochrome P-450 CYP3A Substrates
ATC-Code
  • A10BH51
  • A10BD24
  • A10BD07
  • A10BD29
  • A10BH01
CAS number486460-32-6

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Dipeptidyl peptidase 4MKTPWKVLLGLLGAAALVTIITVPVVLLNKGTDDATADSRKTYTLTDYLK...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknownsubstrate
ATP-dependent translocase ABCB1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate
Organic anion transporter 3MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1422
PubChem 4369359
ChEMBL CHEMBL1422
ChEBI CHEBI:40237