AZD-1656 | CAS#919783-22-5 | glucokinase (GK) activator

AZD-1656
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529914

CAS#: 919783-22-5

Description: 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.

Chemical Structure

AZD-1656

CAS# 919783-22-5

Instruction

Theoretical Analysis

MedKoo Cat#: 529914
Name: AZD-1656
CAS#: 919783-22-5
Chemical Formula: C24H26N6O5
Exact Mass: 478.20
Molecular Weight: 478.510
Elemental Analysis: C, 60.24; H, 5.48; N, 17.56; O, 16.72

Price and Availability

Size	Price	Availability
5mg	USD 450	2 Weeks
25mg	USD 1450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: AZD-1656; AZD1656; AZD 1656;

IUPAC/Chemical Name: 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(2S)-1-methoxypropan-2-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide

InChi Key: FJEJHJINOKKDCW-INIZCTEOSA-N

InChi Code: InChI=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

SMILES Code: O=C(NC1=NC=C(C)N=C1)C2=CC(O[C@@H](C)COC)=CC(OC3=NC=C(C(N4CCC4)=O)N=C3)=C2

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

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: Circadian rhythms play a critical role in regulating metabolism, including daily cycles of feeding/fasting. Glucokinase (GCK) is central for whole-body glucose homeostasis and oscillates according to a circadian clock. GCK activators (GKAs) effectively reduce hyperglycemia, but their use is also associated with hypoglycemia, hyperlipidemia, and hepatic steatosis. Given the circadian rhythmicity and natural postprandial activation of GCK, GKA treatment would benefit from being timed specifically during feeding periods.

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 478.51 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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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