Sitagliptin

CAT: 0013-GTR19161897-01Size: 500 mgDry Ice: NoHazardous: No

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CAT#:0013-GTR19161897-01Size:500 mg

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Description

Sitagliptin is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. This enzyme-inhibiting drug is to be used either alone or in combination with metformin or a thiazolidinedione for control of type 2 diabetes mellitus. The drug works to competitively inhibit a protein/enzyme, dipeptidyl peptidase 4 (DPP-4), that results in an increased amount of active incretins (GLP-1 and GIP), reduced amount of release of glucagon (diminishes its release) and increased release of insulin. (In Vitro) :Sitagliptin phosphate exhibits a potent inhibitory effect on DPP-4 with IC50 of 19 nM from Caco-2 cell extracts. Sitagliptin reduces in vitro migration of isolated splenic CD4 T-cells through a pathway involving cAMP/PKA/Rac1 activation. Stagliptin exerts a novel, direct action in order to stimulate GLP-1 secretion by the intestinal L cell through a DPP-4-independent, protein kinase A- and MEK-ERK1/2-dependent pathway. It reduces the effect of autoimmunity on graft survival. (In Vivo) :In vivo, the ED50 value of sitagliptin phosphate for inhibition of plasma DPP-4 activity is calculated to be 2.3 mg/kg 7 hour postdose and 30 mg/kg 24 hour postdose in freely fed Han-Wistar rats. The streptozotocin-induced type 1 diabetes mouse model exhibits elevated DPP-4 levels in the plasma that can be substantially inhibited in mice on an Sitagliptin phosphate diet. This is achieved by a positive effect on the regulation of hyperglycemia, potentially through prolongation of islet graft survival. The plasma clearance and volume of distribution of Sitagliptin phosphate are higher in rats (40-48 mL/min/kg, 7-9 L/kg) than in dogs (9 mL/min/kg, 3 L/kg) ; and its half-life is shorter in rats,2 hours compared with 4 hours in dogs.

CAS Number

486460-32-6

Product Name Alternative

Field of Research

Pharmacology & Drug Discovery

Purity

>98% (HPLC)

Solubility

Soluble in Water

Smiles

FC (C1=NN=C2CN (C (C[C@H] (N) CC3=CC (F) =C (F) C=C3F) =O) CCN21) (F) F

Molecular Formula

C16H15F6N5O

Molecular Weight

407.32

Storage Conditions

Storage temperature: -20°C. Stability: ≥ 2 years

Notes

For research use only.

Other Product Names

(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

Chemical Information

Sitagliptin

Sitagliptin is a triazolopyrazine that exhibits hypoglycemic activity. It has a role as a hypoglycemic agent, a xenobiotic, a serine proteinase inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor and an environmental contaminant. It is a triazolopyrazine and a trifluorobenzene.

CAS Number	486460-32-6
PubChem CID	4369359
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 Formula	C16H15F6N5O
Molecular Weight	407.31
XLogP	0.7
Topological Polar Surface Area	77
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Heavy Atom Count	28
Formal Charge	0
Complexity	566

SMILES

C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N

InChI

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

InChIKey

MFFMDFFZMYYVKS-SECBINFHSA-N

Chemical Structure

2D Structure

CAS: 486460-32-6

CID: 4369359

Formula: C16H15F6N5O

MW: 407.31

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	407.31
XLogP3	0.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Exact Mass	407.11807909
Monoisotopic Mass	407.11807909
Topological Polar Surface Area	77 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	566
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
RM-S200770-01	Sitagliptin

Sitagliptin

Chemical Information

Alternative Products

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