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Merck
CN

SML3697

Anagliptin

≥98% (HPLC)

Synonym(s):

(S)-N-(2-(2-(2-Cyanopyrrolidin-1-yl)-2-oxoethylamino)-2-methylpropyl)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide, N-[2-({2-[(2S)-2-Cyanopyrrolidine-1-yl]-2-oxoethyl}amino)-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide, SK 0403, SK-0403, SK0403

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About This Item

Empirical Formula (Hill Notation):
C19H25N7O2
CAS Number:
739366-20-2
Molecular Weight:
383.45
UNSPSC Code:
51111800
NACRES:
NA.21
MDL number:
MFCD19443729

Key Documents

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Product Name

Anagliptin, ≥98% (HPLC)

SMILES string

[n]21nc(cc2ncc(c1)C(=O)NCC(NCC(=O)N3[C@@H](CCC3)C#N)(C)C)C

InChI

1S/C19H25N7O2/c1-13-7-16-21-9-14(11-26(16)24-13)18(28)22-12-19(2,3)23-10-17(27)25-6-4-5-15(25)8-20/h7,9,11,15,23H,4-6,10,12H2,1-3H3,(H,22,28)/t15-/m0/s1

InChI key

LDXYBEHACFJIEL-HNNXBMFYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Anagliptin is an orally active, potent and selective dipeptidyl peptidase 4 (DPP-IV; DPP4) inhibitor (DPP4/8/9 IC50 = 3.8/68/60 nM). When administered in vivo (0.3% w/w in diet), anagliptin shows anti-atherosclerotic efficay in apoE-deficient mice and ameliorates diabetes in mice with haploinsufficiency of glucokinase on a high-fat diet.
Orally active, potent and selective dipeptidyl peptidase 4 (DPP-IV; DPP4) inhibitor with anti-atherosclerotic and anti-diabetic efficacy in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000254978
0000254979
0000241805
0000241805
0000254979

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Noriyasu Kato et al.
Bioorganic & medicinal chemistry, 19(23), 7221-7227 (2011-10-25)
In the course of our program for discovery of novel DPP-IV inhibitors, a series of pyrazolo[1,5-a]pyrimidines were found to be novel DPP-IV inhibitors. We identified N-[2-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide hydrochloride (4a) and described its pharmacological profiles.
Keizo Nakaya et al.
Metabolism: clinical and experimental, 62(7), 939-951 (2013-06-26)
Type 2 diabetes is a chronic metabolic disorder characterized by hyperglycemia with insulin resistance and impaired insulin secretion. DPP-4 inhibitors have attracted attention as a new class of anti-diabetic agents for the treatment of type 2 diabetes. We investigated the
Nasib Ervinna et al.
Endocrinology, 154(3), 1260-1270 (2013-01-23)
Dipeptyl peptidase-4 (DPP-4) inhibitors modulate the progression of atherosclerosis. To gain insights into their mechanism of action, 9-wk-old male apolipoprotein E (apoE)-deficient mice were fed a DPP-4 inhibitor, anagliptin-containing diet. The effects of anagliptin were investigated in, a monocyte cell

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