SML3619

Linagliptin

Name: Linagliptin
Brand: SIGMA

≥98% (HPLC), dipeptidyl peptidase IV inhibitor, powder

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

NACRES:

NA.77

Key Documents

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Product Name

Linagliptin, ≥98% (HPLC)

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

SMILES string

N5(C[C@@H](CCC5)N)c1[n](c2c([n]([c]([n]([c]2=O)Cc3nc4c(c(n3)C)cccc4)=O)C)n1)CC#CC

InChI

1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1

InChI key

LTXREWYXXSTFRX-QGZVFWFLSA-N

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This Item	SML3043	SML3526	SML3641
Sigma-Aldrich SML3619 Linagliptin	Sigma-Aldrich SML3043 XL188	Sigma-Aldrich SML3526 AZD8529	Sigma-Aldrich SML3641 Volasertib
form powder	form powder	form powder	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥95% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. -10 to -25°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. -10 to -25°C
solubility DMSO: 2 mg/mL, clear (Warmed)	solubility DMSO: 2 mg/mL, clear	solubility DMSO: 2 mg/mL, clear	solubility DMSO: 2 mg/mL, clear (Warmed)
color white to beige	color white to beige	color white to beige	color white to beige

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).

Orally active, competitive, potent and selective dipeptidyl peptidase IV (DPP-IV; DPP4) inhibitor that improves glucose tolerance in vivo.

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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(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 (BI 1356), a novel xanthine-based dipeptidyl peptidase 4 inhibitor, has a superior potency and longer duration of action compared with other dipeptidyl peptidase-4 inhibitors.

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

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), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes.

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

Chronic treatment with the dipeptidyl peptidase-4 inhibitor BI 1356 [(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] increases basal glucagon-like peptide-1 and improves glycemic control in diabetic rodent models.

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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