Sitagliptin fumarateProduct ingredient for Sitagliptin

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Name
Sitagliptin fumarate
Drug Entry
Sitagliptin

Sitagliptin 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 mellitusLabel,4,1,2. The effect of this medication leads to glucose dependent increases in insulin and decreases in glucagon to improve control of blood sugarLabel,1. Sitagliptin was granted FDA approval on October 16, 20066.

See full entry for Sitagliptin
Accession Number
DBSALT003499
Structure
Similar Structures
Synonyms
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)-, (2E)-2-butenedioate (1:1) / 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 fumarate
UNII
Not Available
CAS Number
837430-24-7
Weight
Average: 523.392
Monoisotopic: 523.12903771
Chemical Formula
C20H19F6N5O5
InChI Key
YRKLLQIZVVYDQY-OIJPFUDISA-N
InChI
InChI=1S/C16H15F6N5O.C4H4O4/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;5-3(6)1-2-4(7)8/h4,6,9H,1-3,5,7,23H2;1-2H,(H,5,6)(H,7,8)/b;2-1+/t9-;/m1./s1
IUPAC Name
(2E)-but-2-enedioic acid; (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
SMILES
OC(=O)\C=C\C(O)=O.N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=C(F)C=C(F)C(F)=C1
ChemSpider
9561797
Wikipedia
Sitagliptin
Predicted Properties
PropertyValueSource
logP1.26Chemaxon
pKa (Strongest Basic)8.66Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area77.04 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity87.49 m3·mol-1Chemaxon
Polarizability32.48 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon