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AZD-1656

Catalog No: 24070
CAS Number: 919783-22-5
Purity: 98% Min.

AZD-1656 is a glucokinase (GK) activator potentially for the treatment of type 2 diabetes and obesity. AZD1656 may achieve its effect either by better control of blood sugar levels or modulation of the immune response through increased Treg migration to inflammation sites.

For research use only. We do not sell to patients.

Chemical Information

NameAZD-1656
Iupac Chemical Name3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(2S)-1-methoxypropan-2-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide
SynonymsAZD-1656; AZD1656; AZD 1656;
Molecular FormulaC24H26N6O5
Molecular Weight478.50
SmileO=C(NC1=NC=C(C)N=C1)C2=CC(O[C@@H](C)COC)=CC(OC3=NC=C(C(N4CCC4)=O)N=C3)=C2
InChiKeyFJEJHJINOKKDCW-INIZCTEOSA-N
InChiInChI=1S/C24H26N6O5/c1-15-10-27-21(12-25-15)29-23(31)17-7-18(34-16(2)14-33-3)9-19(8-17)35-22-13-26-20(11-28-22)24(32)30-5-4-6-30/h7-13,16H,4-6,14H2,1-3H3,(H,27,29,31)/t16-/m0/s1
CAS Number919783-22-5
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Ordering Information

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FormulationOff-white solid
Purity98% Min.
StorageDry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
SolubilitySoluble in DMSO
Handling
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
HS Code
Coming soon.
Targets
Mechanism
Cell study
Animal study
Clinical study

1: Ren Y, Li L, Wan L, Huang Y, Cao S. Glucokinase as an emerging anti-diabetes target and recent progress in the development of its agonists. J Enzyme Inhib Med Chem. 2022 Dec;37(1):606-615. doi: 10.1080/14756366.2021.2025362. PMID: 35067153; PMCID: PMC8788356.


2: Kroon T, Hagstedt T, Alexandersson I, Ferm A, Petersson M, Maurer S, Zarrouki B, Wallenius K, Oakes ND, Boucher J. Chronotherapy with a glucokinase activator profoundly improves metabolism in obese Zucker rats. Sci Transl Med. 2022 Oct 26;14(668):eabh1316. doi: 10.1126/scitranslmed.abh1316. Epub 2022 Oct 26. PMID: 36288279.


3: Chorlton J, Hollowood Z, Dyer C, Lockhart D, Boekman P, McCafferty K, Coffey P, Marelli-Berg F, Martin J. A randomised, double-blind, placebo-controlled, multicentre clinical trial of AZD1656 in diabetic patients hospitalised with COVID-19: The ARCADIA Trial - implications for therapeutic immune modulation. EClinicalMedicine. 2022 Sep;51:101604. doi: 10.1016/j.eclinm.2022.101604. Epub 2022 Aug 18. PMID: 35996565; PMCID: PMC9386394.


4: Norjavaara E, Ericsson H, Sjöberg F, Leonsson-Zachrisson M, Sjöstrand M, Morrow LA, Hompesch M. Glucokinase activators AZD6370 and AZD1656 do not affect the central counterregulatory response to hypoglycemia in healthy males. J Clin Endocrinol Metab. 2012 Sep;97(9):3319-25. doi: 10.1210/jc.2012-1496. Epub 2012 Jun 21. PMID: 22723318.


5: McCafferty K, Hollowood Z, Allen M, Lockhart D, Chorlton J, Martin J. ARCADIA study protocol: a phase II, randomised, double-blind, placebo-controlled clinical trial to assess the safety and efficacy of AZD1656 in patients with diabetes hospitalised with suspected or confirmed COVID-19. BMJ Open. 2021 Dec 1;11(12):e049650. doi: 10.1136/bmjopen-2021-049650. PMID: 34853102; PMCID: PMC8637313.


6: Wilding JP, Leonsson-Zachrisson M, Wessman C, Johnsson E. Dose-ranging study with the glucokinase activator AZD1656 in patients with type 2 diabetes mellitus on metformin. Diabetes Obes Metab. 2013 Aug;15(8):750-9. doi: 10.1111/dom.12088. Epub 2013 Mar 24. PMID: 23464532.


7: Kiyosue A, Hayashi N, Komori H, Leonsson-Zachrisson M, Johnsson E. Dose- ranging study with the glucokinase activator AZD1656 as monotherapy in Japanese patients with type 2 diabetes mellitus. Diabetes Obes Metab. 2013 Oct;15(10):923-30. doi: 10.1111/dom.12100. Epub 2013 Apr 22. PMID: 23522182.


8: Morrow LA, Leonsson-Zachrisson M, Ericsson H, Wollbratt M, Knutsson M, Hompesch M, Norjavaara E. Safety, pharmacokinetics and pharmacodynamics of multiple-ascending doses of the novel glucokinase activator AZD1656 in patients with type 2 diabetes mellitus. Diabetes Obes Metab. 2012 Dec;14(12):1114-22. doi: 10.1111/j.1463-1326.2012.01661.x. Epub 2012 Jul 31. PMID: 22775976.


9: Ericsson H, Röshammar D, Wollbratt M, Heijer M, Persson M, Ueda S, Leonsson- Zachrisson M, Norjavaara E. Tolerability, pharmacokinetics, and pharmacodynamics of the glucokinase activator AZD1656, after single ascending doses in healthy subjects during euglycemic clamp. Int J Clin Pharmacol Ther. 2012 Nov;50(11):765-77. doi: 10.5414/CP201747. PMID: 22943931.


10: Krentz AJ, Morrow L, Petersson M, Norjavaara E, Hompesch M. Effect of exogenously administered glucagon versus spontaneous endogenous counter- regulation on glycaemic recovery from insulin-induced hypoglycaemia in patients with type 2 diabetes treated with a novel glucokinase activator, AZD1656, and metformin. Diabetes Obes Metab. 2014 Nov;16(11):1096-101. doi: 10.1111/dom.12323. Epub 2014 Jul 3. PMID: 24909093.


11: 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. doi: 10.2174/1389557514666140722082713. PMID: 25052034.


12: Ford BE, Chachra SS, Alshawi A, Brennan A, Harnor S, Cano C, Baker DJ, Smith DM, Fairclough RJ, Agius L. Chronic glucokinase activator treatment activates liver Carbohydrate response element binding protein and improves hepatocyte ATP homeostasis during substrate challenge. Diabetes Obes Metab. 2020 Nov;22(11):1985-1994. doi: 10.1111/dom.14111. Epub 2020 Jul 7. PMID: 32519798.


13: Mitchard T, Stewart J. The novel use of a heterozygous knockout mouse for embryofetal development assessment of a glucokinase activator. Birth Defects Res B Dev Reprod Toxicol. 2014 Apr;101(2):152-61. doi: 10.1002/bdrb.21102. PMID: 24753370.


14: Baker DJ, Wilkinson GP, Atkinson AM, Jones HB, Coghlan M, Charles AD, Leighton B. Chronic glucokinase activator treatment at clinically translatable exposures gives durable glucose lowering in two animal models of type 2 diabetes. Br J Pharmacol. 2014 Apr;171(7):1642-54. doi: 10.1111/bph.12504. PMID: 24772484; PMCID: PMC3966745.

Chemical Structure

24070 - AZD-1656 | CAS 919783-22-5

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