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MedKoo Cat#: 319924 | Name: Piragliatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piragliatin, also known as RO4389620, is a glucokinase activator. Piragliatin greatly enhances glucose-induced pancreatic islet respiration and insulin release. Piragliatin lowers plasma glucose both in the postabsorptive state and after a glucose challenge in patients with type 2 diabetes mellitus. Piragliatin has an acute glucose-lowering action in patients with mild type 2 diabetes, mainly mediated through a generalized enhancement of β-cell function and through fasting restricted changes in glucose turnover.

Chemical Structure

Piragliatin
Piragliatin
CAS#625114-41-2

Theoretical Analysis

MedKoo Cat#: 319924

Name: Piragliatin

CAS#: 625114-41-2

Chemical Formula: C19H20ClN3O4S

Exact Mass: 421.0863

Molecular Weight: 421.90

Elemental Analysis: C, 54.09; H, 4.78; Cl, 8.40; N, 9.96; O, 15.17; S, 7.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
RO4389620; RO-4389620; RO 4389620; RO4389620-R1440; Piragliatin.
IUPAC/Chemical Name
(2R)-2-(3-Chloro-4-(methylsulfonyl)phenyl)-3-((1R)-3-oxocyclopentyl)-N-pyrazinylpropanamide
InChi Key
XEANIURBPHCHMG-SWLSCSKDSA-N
InChi Code
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
SMILES Code
O=C(NC1=NC=CN=C1)[C@@H](C2=CC=C(S(=O)(C)=O)C(Cl)=C2)C[C@@H]3CC(CC3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 421.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Georgy A, Zhai S, Liang Z, Boldrin M, Zhi J. Lack of potential pharmacokinetic and pharmacodynamic interactions between piragliatin, a glucokinase activator, and simvastatin in patients with T2DM. J Clin Pharmacol. 2015 Sep 18. doi: 10.1002/jcph.640. [Epub ahead of print] PubMed PMID: 26381165. 2: Zhi J, Zhai S, Georgy A, Liang Z, Boldrin M. Exploratory effects of a strong CYP3A inhibitor (ketoconazole), a strong CYP3A inducer (rifampicin), and concomitant ethanol on piragliatin pharmacokinetics and pharmacodynamics in type 2 diabetic patients. J Clin Pharmacol. 2015 Aug 13. doi: 10.1002/jcph.617. [Epub ahead of print] PubMed PMID: 26272330. 3: Zhi J, Zhai S. Effects of piragliatin, a glucokinase activator, on fasting and postprandial plasma glucose in patients with type 2 diabetes mellitus. J Clin Pharmacol. 2016 Feb;56(2):231-8. doi: 10.1002/jcph.589. Epub 2015 Sep 10. PubMed PMID: 26183686. 4: Kamiyama H, Terauchi Y. [Current status of clinical development of novel anti-diabetic drugs]. Nihon Rinsho. 2015 Mar;73(3):517-22. Japanese. PubMed PMID: 25812383. 5: Grewal AS, Sekhon BS, Lather V. Recent updates on glucokinase activators for the treatment of type 2 diabetes mellitus. Mini Rev Med Chem. 2014;14(7):585-602. Review. PubMed PMID: 25052034. 6: Pettersen JC, Litchfield J, Neef N, Schmidt SP, Shirai N, Walters KM, Enerson BE, Chatman LA, Pfefferkorn JA. The relationship of glucokinase activator-induced hypoglycemia with arteriopathy, neuronal necrosis, and peripheral neuropathy in nonclinical studies. Toxicol Pathol. 2014 Jun;42(4):696-708. doi: 10.1177/0192623314526006. Epub 2014 Apr 24. PubMed PMID: 24771080. 7: Kim MK, Cho JH, Lee JJ, Cheong YH, Son MH, Lee KJ. Differential protective effects of exenatide, an agonist of GLP-1 receptor and Piragliatin, a glucokinase activator in beta cell response to streptozotocin-induced and endoplasmic reticulum stresses. PLoS One. 2013 Sep 19;8(9):e73340. doi: 10.1371/journal.pone.0073340. eCollection 2013. PubMed PMID: 24069189; PubMed Central PMCID: PMC3777936. 8: Dhanesha N, Joharapurkar A, Shah G, Kshirsagar S, Patel V, Patel K, Bahekar R, Jain M. Treatment with exendin-4 improves the antidiabetic efficacy and reverses hepatic steatosis in glucokinase activator treated db/db mice. Eur J Pharmacol. 2013 Aug 15;714(1-3):188-92. doi: 10.1016/j.ejphar.2013.06.015. Epub 2013 Jun 25. PubMed PMID: 23810686. 9: Doliba NM, Fenner D, Zelent B, Bass J, Sarabu R, Matschinsky FM. Repair of diverse diabetic defects of β-cells in man and mouse by pharmacological glucokinase activation. Diabetes Obes Metab. 2012 Oct;14 Suppl 3:109-19. doi: 10.1111/j.1463-1326.2012.01652.x. Review. PubMed PMID: 22928571; PubMed Central PMCID: PMC4433321. 10: Sarabu R, Bizzarro FT, Corbett WL, Dvorozniak MT, Geng W, Grippo JF, Haynes NE, Hutchings S, Garofalo L, Guertin KR, Hilliard DW, Kabat M, Kester RF, Ka W, Liang Z, Mahaney PE, Marcus L, Matschinsky FM, Moore D, Racha J, Radinov R, Ren Y, Qi L, Pignatello M, Spence CL, Steele T, Tengi J, Grimsby J. Discovery of piragliatin--first glucokinase activator studied in type 2 diabetic patients. J Med Chem. 2012 Aug 23;55(16):7021-36. doi: 10.1021/jm3008689. Epub 2012 Aug 1. PubMed PMID: 22809456. 11: Nissim I, Horyn O, Nissim I, Daikhin Y, Wehrli SL, Yudkoff M, Matschinsky FM. Effects of a glucokinase activator on hepatic intermediary metabolism: study with 13C-isotopomer-based metabolomics. Biochem J. 2012 Jun 15;444(3):537-51. doi: 10.1042/BJ20120163. PubMed PMID: 22448977; PubMed Central PMCID: PMC3679927. 12: Doliba NM, Qin W, Najafi H, Liu C, Buettger CW, Sotiris J, Collins HW, Li C, Stanley CA, Wilson DF, Grimsby J, Sarabu R, Naji A, Matschinsky FM. Glucokinase activation repairs defective bioenergetics of islets of Langerhans isolated from type 2 diabetics. Am J Physiol Endocrinol Metab. 2012 Jan 1;302(1):E87-E102. doi: 10.1152/ajpendo.00218.2011. Epub 2011 Sep 27. PubMed PMID: 21952036; PubMed Central PMCID: PMC3328091. 13: Bonadonna RC, Heise T, Arbet-Engels C, Kapitza C, Avogaro A, Grimsby J, Zhi J, Grippo JF, Balena R. 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. J Clin Endocrinol Metab. 2010 Nov;95(11):5028-36. doi: 10.1210/jc.2010-1041. Epub 2010 Aug 25. PubMed PMID: 20739378. 14: Doliba N, Qin W, Najafi H, Wilson D, Grimsby J, Matschinsky F. Piragliatin, an allosteric activator of glucokinase, greatly enhances glucose-induced pancreatic islet respiration and insulin release. Can J Diabetes. 2009;33(3):209. doi: 10.1016/S1499-2671(09)33071-3. Epub 2012 Dec 10. PubMed PMID: 25998593.

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