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Merck
CN

SML1946

Sigma-Aldrich

AM-9074

≥98% (HPLC)

Synonym(s):

(R)-1-(4-((5-Methoxypyridin-3-yl)oxy)-5-(tetrahydro-2H-pyran-3-yl)pyridin-2-yl)-3-methylurea, Urea, N-[4-[(5-methoxy-3-pyridinyl)oxy]-5-[(3R)-tetrahydro-2H-pyran-3-yl]-2-pyridinyl]-N′-methyl-

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About This Item

Empirical Formula (Hill Notation):
C18H22N4O4
CAS Number:
1442677-92-0
Molecular Weight:
358.39
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CNC(NC1=CC(OC2=CC(OC)=CN=C2)=C([C@H]3CCCOC3)C=N1)=O

InChI

1S/C18H22N4O4/c1-19-18(23)22-17-7-16(26-14-6-13(24-2)8-20-9-14)15(10-21-17)12-4-3-5-25-11-12/h6-10,12H,3-5,11H2,1-2H3,(H2,19,21,22,23)/t12-/m0/s1

InChI key

APSOPISMEDAYTH-LBPRGKRZSA-N

Biochem/physiol Actions

AM-9074 is a potent activator of glucokinase, which catalyzes the phosphorylation of glucose to glucose-6-phosphate. AM-9074 had an EC50 value of 160 nM with good solubility, oral bioavailability and acceptable clearance in rodents, and was shown to lower plasma glucose levels.
Glucokinase activator

Storage Class Code

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
0000045442
0000045443
0000042140

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Todd J Kohn et al.
ACS medicinal chemistry letters, 7(7), 666-670 (2016-07-21)
Two 1-(4-aryl-5-alkyl-pyridin-2-yl)-3-methylurea glucokinase activators were identified with robust in vivo efficacy. These two compounds possessed higher solubilities than the previously identified triaryl compounds (i.e., AM-2394). Structure-activity relationship studies are presented along with relevant pharmacokinetic and in vivo data.

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