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
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
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
Title | Date | PubMed |
---|---|---|
Identification of YAC clones containing the mutable slender glume locus slg in rice (Oryza sativa L.). | 2001 Feb |
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Hindlimb unloading and female gender attenuate baroreflex-mediated sympathoexcitation. | 2005 Nov |
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Glucokinase activators (GKAs) promise a new pharmacotherapy for diabetics. | 2010 Jun 16 |
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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 |
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Skeletal muscle proteomics: carbohydrate metabolism oscillates with seasonal and torpor-arousal physiology of hibernation. | 2011 Nov |
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Repair of diverse diabetic defects of β-cells in man and mouse by pharmacological glucokinase activation. | 2012 Oct |
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Lack of Potential Pharmacokinetic and Pharmacodynamic Interactions Between Piragliatin, a Glucokinase Activator, and Simvastatin in Patients With Type 2 Diabetes Mellitus. | 2016 Jun |
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Pharmacokinetic and Pharmacodynamic Drug Interaction Study of Piragliatin, a Glucokinase Activator, and Glyburide, a Sulfonylurea, in Type 2 Diabetic Patients. | 2016 Nov |
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Dose-Dependent Effect of Piragliatin, a Glucokinase Activator, on the QT Interval Following Short-Term Multiple Doses in Patients With Type 2 Diabetes Mellitus. | 2017 May |
|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20739378
Single-dose 25 or 100 mg
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:02:08 UTC 2023
by
admin
on
Fri Dec 15 16:02:08 UTC 2023
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Record UNII |
BM1HR7IP1L
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29711
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C77587
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C553963
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10432339
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Related Record | Type | Details | ||
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TARGET -> ACTIVATOR |
Related Record | Type | Details | ||
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ACTIVE MOIETY |