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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H20BN3O3
Molecular Weight 241.095
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DUTOGLIPTIN

SMILES

OB(O)[C@@H]1CCCN1C(=O)CN[C@@H]2CCNC2

InChI

InChIKey=DVJAMEIQRSHVKC-BDAKNGLRSA-N
InChI=1S/C10H20BN3O3/c15-10(7-13-8-3-4-12-6-8)14-5-1-2-9(14)11(16)17/h8-9,12-13,16-17H,1-7H2/t8-,9+/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H20BN3O3
Molecular Weight 241.095
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dutogliptin (PHX-1149T) is a small-molecule dipeptidyl peptidase-4 (DPP-4) inhibitor for the potential oral treatment of type 2 diabetes mellitus (T2DM). DPP-4 quickly degrades the insulin secretory hormones, glucose-dependent insulinotropic peptide and glucagon-like peptide-1; thus inhibiting the degradation of these hormones is a viable treatment option for patients with T2DM. In preclinical studies, dutogliptin potently inhibited DPP-4 and, in a model of T2DM, treatment with dutogliptin improved glucose homeostasis. Pharmacokinetic analyses in animals, healthy individuals and patients with T2DM demonstrated that drug exposure increased in a dose-dependent manner. Results from phase II clinical trials indicated that once-daily dutogliptin, in combination with other oral diabetes therapies, reduces postprandial blood glucose and HbA1c levels, both indicators of successful diabetes management. The incidence of adverse events was similar in treatment and placebo groups, with slightly more headache, arthralgia, sinusitis, and dizziness occurring in the 400 mg dutogliptin group compared with placebo. Phase II clinical trial for the myocardial infarction treatment is underway.

Approval Year

PubMed

PubMed

TitleDatePubMed
Dutogliptin, a dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes mellitus.
2010 Apr
Small molecule dipeptidylpeptidase IV inhibitors under investigation for diabetes mellitus therapy.
2011 Jun
Population pharmacokinetic analysis of dutogliptin, a selective dipeptidyl peptidase-4 inhibitor.
2014 Jul
Dipeptidyl peptidase-4 inhibitors and heart failure: a meta-analysis of randomized clinical trials.
2014 Jul
Comparison of dipeptidyl peptidase-4 inhibitors and pioglitazone combination therapy versus pioglitazone monotherapy in type 2 diabetes: A system review and meta-analysis.
2018 Nov

Sample Use Guides

Substance Class Chemical
Created
by admin
on Wed Jul 05 23:38:17 UTC 2023
Edited
by admin
on Wed Jul 05 23:38:17 UTC 2023
Record UNII
38EAO245ZX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DUTOGLIPTIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
Dutogliptin [WHO-DD]
Common Name English
[(2R)-1-{[(3R)-Pyrrolidin-3-ylamino]acetyl}pyrrolidin-2-yl]boronic acid
Systematic Name English
PHX-1149
Code English
dutogliptin [INN]
Common Name English
PHX1149
Code English
DUTOGLIPTIN [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98086
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID301005713
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
NCI_THESAURUS
C87492
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
CAS
852329-66-9
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
EVMPD
SUB32930
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
SMS_ID
100000125989
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
INN
8986
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
FDA UNII
38EAO245ZX
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
DRUG BANK
DB11723
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
MESH
C552164
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
USAN
UU-14
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
PUBCHEM
11253490
Created by admin on Wed Jul 05 23:38:17 UTC 2023 , Edited by admin on Wed Jul 05 23:38:17 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY