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SML3619

Sigma-Aldrich

Linagliptin

≥98% (HPLC)

Synonym(s):

(R)-8-(3-Amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione, 8-(3-(R)-Aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydropurine-2,6-dione, BI 1356, BI-1356, BI1356, Ondero

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About This Item

Empirical Formula (Hill Notation):
C25H28N8O2
CAS Number:
668270-12-0
Molecular Weight:
472.54
MDL number:
MFCD14635356
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

Biochem/physiol Actions

Linagliptin is an orally active, competitive, potent and selective dipeptidyl peptidase IV (DPP4; DPP-IV) inhibitor (IC50 = 1 nM vs. 19 nM/sitagliptin, 24 nM/alogliptin, 50 nM/saxagliptin, 62 nM/vildagliptin) with no inhibitory potency against DPP-2/8/9 (IC50 >10 µM). Sitagliptin improves glucose tolerance and exhibits efficacy in diabetic rodent models in vivo (1-10 mg/kg via daily p.o. in mice and rats).

hcodes

H412

Hazard Classifications

Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Matthias Eckhardt et al.
Journal of medicinal chemistry, 50(26), 6450-6453 (2007-12-07)
A new chemical class of potent DPP-4 inhibitors structurally derived from the xanthine scaffold for the treatment of type 2 diabetes has been discovered and evaluated. Systematic structural variations have led to 1 (BI 1356), a highly potent, selective, long-acting
Leo Thomas et al.
The Journal of pharmacology and experimental therapeutics, 325(1), 175-182 (2008-01-29)
BI 1356 [proposed trade name ONDERO; (R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione] is a novel dipeptidyl peptidase (DPP)-4 inhibitor under clinical development for the treatment of type 2 diabetes. In this study, we investigated the potency, selectivity, mechanism, and duration of action of BI 1356
Leo Thomas et al.
The Journal of pharmacology and experimental therapeutics, 328(2), 556-563 (2008-10-31)
Antidiabetic effects of dipeptidyl peptidase-4 (DPP-4) inhibitors are exerted by potentiation of the biological activity of incretin hormones like glucagon-like peptide (GLP)-1. BI 1356 [proposed trade name Ondero; (R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione] is a novel competitive, selective, potent, and long-acting DPP-4 inhibitor under

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