Compounds > dutogliptin
Page last updated: 2024-10-14

dutogliptin

Cross-References

ID SourceID
PubMed CID11253490
CHEMBL ID4296719
SCHEMBL ID164106
MeSH IDM0549950

Synonyms (32)

Synonym
D09333
dutogliptin (usan)
852329-66-9
boronic acid, ((2r)-1-(((3r)-3-pyrrolidinylamino)acetyl)-2-pyrrolidinyl)-
dutogliptin ,
phx1149
dutogliptin [usan:inn]
38eao245zx ,
unii-38eao245zx
((2r)-1-(((3r)-pyrrolidin-3-ylamino)acetyl)pyrrolidin-2-yl)boronic acid
dutogliptin [who-dd]
[(2r)-1-{[(3r)-pyrrolidin-3-ylamino]acetyl}pyrrolidin-2-yl]boronic acid
dutogliptin [usan]
dutogliptin [inn]
SCHEMBL164106
[(2r)-1-[[(3r)-3-pyrrolidinylamino]acetyl]-2-pyrrolidinyl]-boronic acid
[(2r)-1-[2-[[(3r)-pyrrolidin-3-yl]amino]acetyl]pyrrolidin-2-yl]boronic acid
AKOS027326882
CS-6633
HY-10286
[(2r)-1-(2-{[(3r)-pyrrolidin-3-yl]amino}acetyl)pyrrolidin-2-yl]boronic acid
((r)-1-(((r)-pyrrolidin-3-yl)glycyl)pyrrolidin-2-yl)boronic acid
DB11723
BCP24061
phx-1149 free base
Q27256778
CHEMBL4296719
MS-23411
{1-[n-(pyrrolidin-3-yl)glycyl]pyrrolidin-2-yl}boronic acid
DTXSID301005713
bdbm50589214
CJB32966

Research Excerpts

Overview

Dutogliptin is a selective dipeptidyl peptidase-4 inhibitor shown to be efficacious and safe in patients with type 2 diabetes mellitus (T2DM)

ExcerptReference
"Dutogliptin is a selective dipeptidyl peptidase-4 inhibitor shown to be efficacious and safe in patients with type 2 diabetes mellitus (T2DM). "( Population pharmacokinetic analysis of dutogliptin, a selective dipeptidyl peptidase-4 inhibitor.
Gosselin, NH; Li, J; Marier, JF; Mouksassi, MS, 2014)
"Dutogliptin is a novel, orally available, potent, and selective DPP4 inhibitor that improves glycemic control in type 2 diabetic patients. "( Evaluation of the potential for pharmacokinetic and pharmacodynamic interactions between dutogliptin, a novel DPP4 inhibitor, and metformin, in type 2 diabetic patients.
Boyea, T; Cherrington, JM; Guler, HP; Klemm, K; Li, J; O'Farrell, AM; Schwartz, S, 2010)

Treatment

ExcerptReference
"Dutogliptin treatment for 12 weeks improved glycaemic control in patients with type 2 diabetes who were on a background medication of metformin, a TZD or metformin plus a TZD. "( Dutogliptin, a selective DPP4 inhibitor, improves glycaemic control in patients with type 2 diabetes: a 12-week, double-blind, randomized, placebo-controlled, multicentre trial.
Alpizar, M; Bennett, C; Cherrington, JM; Guler, HP; Li, J; O'Farrell, AM; Pattzi, HM; Pitale, S, 2010)

Toxicity

ExcerptReference
" No related serious adverse events occurred."( Safety, tolerability, pharmacokinetics and pharmacodynamics of parenterally administered dutogliptin: A prospective dose-escalating trial.
Buchtele, N; Derhaschnig, U; Firbas, C; Jilma, B; Karch, R; Nix, D; Schenk, R; Schoergenhofer, C; Schwameis, M, 2020)
"Parenteral injection of dutogliptin was safe and subcutaneous bioavailability is excellent."( Safety, tolerability, pharmacokinetics and pharmacodynamics of parenterally administered dutogliptin: A prospective dose-escalating trial.
Buchtele, N; Derhaschnig, U; Firbas, C; Jilma, B; Karch, R; Nix, D; Schenk, R; Schoergenhofer, C; Schwameis, M, 2020)

Pharmacokinetics

Population pharmacokinetic (PK) analysis of dutogliptin was performed based on data collected in 561 healthy subjects and patients with T2DM enrolled in Phase I and II studies. The objective of this study was to evaluate the potential pharmacokinetics and pharmacodynamic interactions.

ExcerptReference
" The objective of this study was to evaluate the potential pharmacokinetic and pharmacodynamic interactions, as well as the tolerability, of dutogliptin and metformin alone and in combination in type 2 diabetic patients."( Evaluation of the potential for pharmacokinetic and pharmacodynamic interactions between dutogliptin, a novel DPP4 inhibitor, and metformin, in type 2 diabetic patients.
Boyea, T; Cherrington, JM; Guler, HP; Klemm, K; Li, J; O'Farrell, AM; Schwartz, S, 2010)
" There is no need to consider pharmacokinetic and pharmacodynamic interactions when determining the dosage of either agent for co-administration."( Evaluation of the potential for pharmacokinetic and pharmacodynamic interactions between dutogliptin, a novel DPP4 inhibitor, and metformin, in type 2 diabetic patients.
Boyea, T; Cherrington, JM; Guler, HP; Klemm, K; Li, J; O'Farrell, AM; Schwartz, S, 2010)
" Population pharmacokinetic (PK) analysis of dutogliptin was performed based on data collected in 561 healthy subjects and patients with T2DM enrolled in Phase I and II studies to assess sources of variability and support dosing rationale."( Population pharmacokinetic analysis of dutogliptin, a selective dipeptidyl peptidase-4 inhibitor.
Gosselin, NH; Li, J; Marier, JF; Mouksassi, MS, 2014)

Compound-Compound Interactions

The REC-DUT-002 trial is the first to evaluate dutogliptin in combination with G-CSF in patients with STEMI. Dutoglisptin, a novel DPP4 inhibitor, combined with stem cell mobilization using G- CSF significantly improved survival and reduced infarct size in a murine model.

ExcerptReference
" Dutogliptin, a novel DPP4 inhibitor, combined with stem cell mobilization using G-CSF significantly improved survival and reduced infarct size in a murine model."( "Protocol for a phase 2, randomized, double-blind, placebo-controlled, safety and efficacy study of dutogliptin in combination with filgrastim in early recovery post-myocardial infarction": study protocol for a randomized controlled trial.
Henauer, S; Jilma, B; Kubica, J; Nix, D; Povsic, TJ; Schatz, RA; Selvanayagam, JB; von Lewinski, D; Wallner, M, 2020)
"We test the safety and tolerability and efficacy of dutogliptin in combination with filgrastim (G-CSF) in patients with STEMI (EF < 45%) following percutaneous coronary intervention (PCI)."( "Protocol for a phase 2, randomized, double-blind, placebo-controlled, safety and efficacy study of dutogliptin in combination with filgrastim in early recovery post-myocardial infarction": study protocol for a randomized controlled trial.
Henauer, S; Jilma, B; Kubica, J; Nix, D; Povsic, TJ; Schatz, RA; Selvanayagam, JB; von Lewinski, D; Wallner, M, 2020)
"The REC-DUT-002 trial is the first to evaluate dutogliptin in combination with G-CSF in patients with STEMI."( "Protocol for a phase 2, randomized, double-blind, placebo-controlled, safety and efficacy study of dutogliptin in combination with filgrastim in early recovery post-myocardial infarction": study protocol for a randomized controlled trial.
Henauer, S; Jilma, B; Kubica, J; Nix, D; Povsic, TJ; Schatz, RA; Selvanayagam, JB; von Lewinski, D; Wallner, M, 2020)

Bioavailability

ExcerptReference
" Subcutaneous bioavailability was approximately 100%."( Safety, tolerability, pharmacokinetics and pharmacodynamics of parenterally administered dutogliptin: A prospective dose-escalating trial.
Buchtele, N; Derhaschnig, U; Firbas, C; Jilma, B; Karch, R; Nix, D; Schenk, R; Schoergenhofer, C; Schwameis, M, 2020)
"Parenteral injection of dutogliptin was safe and subcutaneous bioavailability is excellent."( Safety, tolerability, pharmacokinetics and pharmacodynamics of parenterally administered dutogliptin: A prospective dose-escalating trial.
Buchtele, N; Derhaschnig, U; Firbas, C; Jilma, B; Karch, R; Nix, D; Schenk, R; Schoergenhofer, C; Schwameis, M, 2020)

Dosage Studied

ExcerptReference
" There is no need to consider pharmacokinetic and pharmacodynamic interactions when determining the dosage of either agent for co-administration."( Evaluation of the potential for pharmacokinetic and pharmacodynamic interactions between dutogliptin, a novel DPP4 inhibitor, and metformin, in type 2 diabetic patients.
Boyea, T; Cherrington, JM; Guler, HP; Klemm, K; Li, J; O'Farrell, AM; Schwartz, S, 2010)
" Population pharmacokinetic (PK) analysis of dutogliptin was performed based on data collected in 561 healthy subjects and patients with T2DM enrolled in Phase I and II studies to assess sources of variability and support dosing rationale."( Population pharmacokinetic analysis of dutogliptin, a selective dipeptidyl peptidase-4 inhibitor.
Gosselin, NH; Li, J; Marier, JF; Mouksassi, MS, 2014)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dipeptidyl peptidase 4Homo sapiens (human)IC50 (µMol)0.02500.00010.444410.0000AID1850423
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
behavioral fear responseDipeptidyl peptidase 4Homo sapiens (human)
response to hypoxiaDipeptidyl peptidase 4Homo sapiens (human)
proteolysisDipeptidyl peptidase 4Homo sapiens (human)
cell adhesionDipeptidyl peptidase 4Homo sapiens (human)
positive regulation of cell population proliferationDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of extracellular matrix disassemblyDipeptidyl peptidase 4Homo sapiens (human)
peptide hormone processingDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated endocytosis of virus by host cellDipeptidyl peptidase 4Homo sapiens (human)
T cell costimulationDipeptidyl peptidase 4Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrinDipeptidyl peptidase 4Homo sapiens (human)
locomotory exploration behaviorDipeptidyl peptidase 4Homo sapiens (human)
psychomotor behaviorDipeptidyl peptidase 4Homo sapiens (human)
T cell activationDipeptidyl peptidase 4Homo sapiens (human)
endothelial cell migrationDipeptidyl peptidase 4Homo sapiens (human)
symbiont entry into host cellDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated virion attachment to host cellDipeptidyl peptidase 4Homo sapiens (human)
negative chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
membrane fusionDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of neutrophil chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
glucagon processingDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
virus receptor activityDipeptidyl peptidase 4Homo sapiens (human)
protease bindingDipeptidyl peptidase 4Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
signaling receptor bindingDipeptidyl peptidase 4Homo sapiens (human)
protein bindingDipeptidyl peptidase 4Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 4Homo sapiens (human)
protein homodimerization activityDipeptidyl peptidase 4Homo sapiens (human)
chemorepellent activityDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular regionDipeptidyl peptidase 4Homo sapiens (human)
lysosomal membraneDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
focal adhesionDipeptidyl peptidase 4Homo sapiens (human)
cell surfaceDipeptidyl peptidase 4Homo sapiens (human)
membraneDipeptidyl peptidase 4Homo sapiens (human)
apical plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
lamellipodiumDipeptidyl peptidase 4Homo sapiens (human)
endocytic vesicleDipeptidyl peptidase 4Homo sapiens (human)
lamellipodium membraneDipeptidyl peptidase 4Homo sapiens (human)
membrane raftDipeptidyl peptidase 4Homo sapiens (human)
intercellular canaliculusDipeptidyl peptidase 4Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1850423Inhibition of DPP-4 (unknown origin)2022Bioorganic & medicinal chemistry, 06-01, Volume: 63Boron-Containing heterocycles as promising pharmacological agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (57.14)24.3611
2020's3 (42.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (57.14%)5.53%
Reviews2 (28.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other1 (14.29%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		3.1610pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
metformin
Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.		8.4411guanidinesenvironmental contaminant;
geroprotector;
hypoglycemic agent;
xenobiotic
quinazolines
Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.		3.1610azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinazolines
1,2-dihydro-1-hydroxy-6-methyl-2-(propanesulfonyl)-thieno(3,2d)(1,2,3)-diazaborine
1,2-dihydro-1-hydroxy-6-methyl-2-(propanesulfonyl)-thieno(3,2D)(1,2,3)-diazaborine: enoyl-ACP reductase inhibitor; synthetic antibacterial agent which inhibits lipopolysaccharide biosyn; structure given in first source		3.5110
talabostat
talabostat: an antineoplastic agent; structure in first source		3.5110
linagliptin
Linagliptin: A purine and quinazoline derivative that functions as an INCRETIN and DIPEPTIDYL-PEPTIDASE IV INHIBTOR. It is used as a HYPOGLYCEMIC AGENT in the treatment of TYPE II DIABETES MELLITUS.. linagliptin : A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type II diabetes.		3.1610aminopiperidine;
quinazolines		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
hypoglycemic agent
alogliptin
alogliptin: structure in first source. alogliptin : A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes.		3.1610nitrile;
piperidines;
primary amino compound;
pyrimidines		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
hypoglycemic agent
tavaborole
tavaborole: has antifungal activity; structure in first source. tavaborole : A member of the class of benzoxaboroles that is 1,3-dihydro-1-hydroxy-2,1-benzoxaborole substituted at position 5 by a fluoro group. A topical antifungal agent used for the treatment of onychomycosis (fungal infection of the toenails and fingernails).		3.5110benzoxaborole;
organofluorine compound		antifungal agent;
EC 6.1.1.4 (leucine--tRNA ligase) inhibitor;
protein synthesis inhibitor
scyx 7158
[no description available]		3.5110(trifluoromethyl)benzenes
piperidines
Piperidines: A family of hexahydropyridines.		3.1610
ConditionIndicatedRelationship StrengthStudiesTrials
ST Elevated Myocardial Infarction
[description not available]		03.6411
ST Elevation Myocardial Infarction
A clinical syndrome defined by MYOCARDIAL ISCHEMIA symptoms; persistent elevation in the ST segments of the ELECTROCARDIOGRAM; and release of BIOMARKERS of myocardial NECROSIS (e.g., elevated TROPONIN levels). ST segment elevation in the ECG is often used in determining the treatment protocol (see also NON-ST ELEVATION MYOCARDIAL INFARCTION).		03.6411
Diabetes Mellitus, Adult-Onset
[description not available]		05.8442
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		17.8442
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.110