ABT279 - CAS 676559-83-4
Catalog number: 676559-83-4
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C21H25N5O3
Molecular Weight:
395.46
COA:
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Description:
ABT279 is a bio-active chemical coumpound. It is used for the treatment of type 2 diabetes. It was developed by Abbvie and was in clinical phase 1 trial, but now it is terminated.
Purity:
98%
Appearance:
Solid powder
Synonyms:
ABT-279;2-[4-[[2-[(2S,5R)-2-Cyano-5-ethynyl-1-pyrrolidinyl]-2-oxoethyl]amino]-4-methyl-1-piperidinyl]-4-pyridinecarboxylic acid;4-Pyridinecarboxylic acid, 2-(4-((2-((2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl)-2-oxoethyl)amino)-4-methyl-1-piperidinyl)-
Solubility:
Soluble in DMSO, not in water
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
ABT279 is used for the treatment of type 2 diabetes.
Quality Standard:
In-house standard
Quantity:
Grams to Kilograms
Boiling Point:
721.2±60.0 °C | Condition: Press: 760 Torr
Density:
1.32±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
FIMRNLAKAARHPD-IRXDYDNUSA-N
InChI:
InChI=1S/C21H25N5O3/c1-3-16-4-5-17(13-22)26(16)19(27)14-24-21(2)7-10-25(11-8-21)18-12-15(20(28)29)6-9-23-18/h1,6,9,12,16-17,24H,4-5,7-8,10-11,14H2,2H3,(H,28,29)/t16-,17-/m0/s1
Canonical SMILES:
CC1(CCN(CC1)C2=NC=CC(=C2)C(=O)O)NCC(=O)N3C(CCC3C#N)C#C
Current Developer:
ABT279 was developed by Abbvie and was in clinical phase 1 trial, but now it is terminated.
1.Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.
Havale SH;Pal M Bioorg Med Chem. 2009 Mar 1;17(5):1783-802. doi: 10.1016/j.bmc.2009.01.061. Epub 2009 Jan 31.
Emerging as an epidemic of the 21st century type 2 diabetes has become a major health problem throughout the globe. The number of deaths attributable to diabetes reflects the insufficient glycemic control achieved with the treatments used in recent past. DPP-4 inhibitors have been investigated as a new therapy with novel mechanisms of action and improved tolerability. DPP-4, a protease that specifically cleaves dipeptides from proteins and oligopeptides after a penultimate N-terminal proline or alanine, is involved in the degradation of a number of neuropeptides, peptide hormones and cytokines, including the incretins GLP-1 and GIP. As soon as released from the gut in response to food intake, GLP-1 and GIP exert a potent glucose-dependent insulinotropic action, thereby playing a key role in the maintenance of post-meal glycemic control. Consequently, inhibiting DPP-4 prolongs the action of GLP-1 and GIP, which in turn improves glucose homeostasis with a low risk of hypoglycemia and potential for disease modification. Indeed, clinical trials involving diabetic patients have shown improved glucose control by administering DPP-4 inhibitors, thus demonstrating the benefit of this promising new class of antidiabetics.
2.Discovery of 2-[4-{{2-(2S,5R)-2-cyano-5-ethynyl-1-pyrrolidinyl]-2-oxoethyl]amino]- 4-methyl-1-piperidinyl]-4-pyridinecarboxylic acid (ABT-279): a very potent, selective, effective, and well-tolerated inhibitor of dipeptidyl peptidase-IV, useful for the treatment of diabetes.
Madar DJ;Kopecka H;Pireh D;Yong H;Pei Z;Li X;Wiedeman PE;Djuric SW;Von Geldern TW;Fickes MG;Bhagavatula L;McDermott T;Wittenberger S;Richards SJ;Longenecker KL;Stewart KD;Lubben TH;Ballaron SJ;Stashko MA;Long MA;Wells H;Zinker BA;Mika AK;Beno DW;Kempf-Grote AJ;Polakowski J;Segreti J;Reinhart GA;Fryer RM;Sham HL;Trevillyan JM J Med Chem. 2006 Oct 19;49(21):6416-20.
Dipeptidyl peptidase-IV (DPP-IV) inhibitors are poised to be the next major drug class for the treatment of type 2 diabetes. Structure-activity studies of substitutions at the C5 position of the 2-cyanopyrrolidide warhead led to the discovery of potent inhibitors of DPP-IV that lack activity against DPP8 and DPP9. Further modification led to an extremely potent (Ki(DPP)(-)(IV) = 1.0 nM) and selective (Ki(DPP8) > 30 microM; Ki(DPP9) > 30 microM) clinical candidate, ABT-279, that is orally available, efficacious, and remarkably safe in preclinical safety studies.
3.Retrospective and Prospective Human Intravenous and Oral Pharmacokinetic Projection of Dipeptidyl peptidase-IV Inhibitors Using Simple Allometric Principles - Case Studies of ABT-279, ABT-341, Alogliptin, Carmegliptin, Sitagliptin and Vildagliptin.
Gilibili RR;Bhamidipati RK;Mullangi R;Srinivas NR J Pharm Pharm Sci. 2015;18(3):434-48.
PURPOSE: ;The purpose of this exercise was to explore the utility of allometric scaling approach for the prediction of intravenous and oral pharmacokinetics of six dipeptidy peptidase-IV (DPP-IV) inhibitors viz. ABT-279, ABT-341, alogliptin, carmegliptin, sitagliptin and vildagliptin.;METHODS: ;The availability of intravenous and oral pharmacokinetic data in animals enabled the allometry scaling of 6 DPP-IV inhibitors. The relationship between the main pharmacokinetic parameters [viz. volume of distribution (Vd) and clearance (CL)] and body weight was studied across three or four mammalian species, using double logarithmic plots to predict the human pharmacokinetic parameters of CL and Vd using simple allometry.;RESULTS: ;A simply allometry relationship: Y = aWb was found to be adequate for the prediction of intravenous and oral human clearance/volume of distribution for DPP-IV inhibitors. The allometric equations for alogliptin, carmegliptin, sitagliptin, vildagliptin, ABT-279 and ABT-341 were 1.867W0.780, 1.170W0.756, 2.020W0.529, 1.959 W0.847, 0.672 W1.016, 1.077W 0.649, respectively, to predict intravenous clearance (CL) and the corresponding equations to predict intravenous volume of distribution (Vd) were: 3.
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