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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H20ClN3O4S
Molecular Weight 421.898
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRAGLIATIN

SMILES

[H][C@]3(C[C@@H](C(=O)NC1=CN=CC=N1)C2=CC=C(C(Cl)=C2)S(C)(=O)=O)CCC(=O)C3

InChI

InChIKey=XEANIURBPHCHMG-SWLSCSKDSA-N
InChI=1S/C19H20ClN3O4S/c1-28(26,27)17-5-3-13(10-16(17)20)15(9-12-2-4-14(24)8-12)19(25)23-18-11-21-6-7-22-18/h3,5-7,10-12,15H,2,4,8-9H2,1H3,(H,22,23,25)/t12-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H20ClN3O4S
Molecular Weight 421.898
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Piragliatin is a nonessential, mixed-type (i.e. increases maximal velocity and affinity of glucokinase for glucose) small-molecule activators of glucokinase. Preclinical pharmacology studies confirmed that piragliatin had activity in both pancreatic beta-cell and hepatic cell glucose metabolism. Piragliatin augmented glucose-stimulated insulin secretion (GSIS) in human islets from both normal individuals and patients with type 2 diabetes, primarily by left-shifting the glucose dependency curve of GSIS. In healthy volunteers a single administration of piragliatin showed dose-dependent reduction of fasting plasma glucose. The glucokinase activator piragliatin has an acute glucose-lowering action in patients with mild type 2 diabetes, mainly mediated through a generalized enhancement of beta-cell function and through fasting restricted changes in glucose turnover. Headache and mild hypoglycemia were the most frequent adverse events associated with piragliatin treatment. The effect of piragliatin treatment on the QTc interval was dose/exposure dependent following short-term multiple doses. Piragliatin had been in phase II clinical trial for the treatment of Type 2 diabetes mellitus. However, this development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Glucokinase activators (GKAs) promise a new pharmacotherapy for diabetics.
2010 Jun 16
Piragliatin (RO4389620), a novel glucokinase activator, lowers plasma glucose both in the postabsorptive state and after a glucose challenge in patients with type 2 diabetes mellitus: a mechanistic study.
2010 Nov
Treatment with exendin-4 improves the antidiabetic efficacy and reverses hepatic steatosis in glucokinase activator treated db/db mice.
2013 Aug 15
Immunogenicity of aluminum-adsorbed hepatitis A vaccine (Havrix®) administered as a third dose after primary doses of Japanese aluminum-free hepatitis A vaccine (Aimmugen®) for Japanese travelers to endemic countries.
2017 Nov 7
Chemoselective methylene oxidation in aromatic molecules.
2019 Mar
Patents

Sample Use Guides

Single-dose 25 or 100 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:08 GMT 2023
Record UNII
BM1HR7IP1L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRAGLIATIN
INN   USAN  
INN   USAN  
Official Name English
Piragliatin [WHO-DD]
Common Name English
RO-4389620
Code English
(2R)-2-[3-Chloro-4-(methylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]-N-pyrazinylpropanamide
Systematic Name English
piragliatin [INN]
Common Name English
RO-4389620-R1440
Code English
RO4389620-R1440
Code English
PIRAGLIATIN [USAN]
Common Name English
R04389620\
Code English
Classification Tree Code System Code
NCI_THESAURUS C29711
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
Code System Code Type Description
INN
8839
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
PRIMARY
NCI_THESAURUS
C77587
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
PRIMARY
EVMPD
SUB122949
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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FDA UNII
BM1HR7IP1L
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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MESH
C553963
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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ChEMBL
CHEMBL1783734
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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SMS_ID
100000145109
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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EPA CompTox
DTXSID3048520
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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USAN
TT-89
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
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CAS
625114-41-2
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
PRIMARY
PUBCHEM
10432339
Created by admin on Fri Dec 15 16:02:08 GMT 2023 , Edited by admin on Fri Dec 15 16:02:08 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
Related Record Type Details
ACTIVE MOIETY