MK-3903 | CAS#1219737-12-8 | AMPK activator

MedKoo Cat#: 530973 | Name: MK-3903

Description:

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

MK-3903 is a potent and selective AMPK activator (EC50 = 8 nM). MK-3903 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice. Chronic oral administration of MK-3903 robustly increased ACC phosphorylation in liver with more modest effects in skeletal muscle. Treatment of various mouse models with MK-3903 resulted in expected alterations in lipid metabolism and improvements in a measure of insulin sensitization.

Chemical Structure

MK-3903

CAS#1219737-12-8

Theoretical Analysis

MedKoo Cat#: 530973

Name: MK-3903

CAS#: 1219737-12-8

Chemical Formula: C27H19ClN2O3

Exact Mass: 454.1084

Molecular Weight: 454.91

Elemental Analysis: C, 71.29; H, 4.21; Cl, 7.79; N, 6.16; O, 10.55

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,850.00	Ready to ship

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Related CAS #

No Data

Synonym

MK-3903; MK 3903; MK3903.

IUPAC/Chemical Name

5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid

InChi Key

FIKQZQDYGXAUHC-UHFFFAOYSA-N

InChi Code

InChI=1S/C27H19ClN2O3/c1-16-7-12-20(13-21(16)26(31)32)33-27-29-24-14-22(23(28)15-25(24)30-27)19-10-8-18(9-11-19)17-5-3-2-4-6-17/h2-15H,1H3,(H,29,30)(H,31,32)

SMILES Code

O=C(O)C1=CC(OC2=NC3=CC(C4=CC=C(C5=CC=CC=C5)C=C4)=C(Cl)C=C3N2)=CC=C1C

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

AMP-activated protein kinase (AMPK) plays an essential role as a cellular energy sensor and master regulator of metabolism in eukaryotes. Dysregulated lipid and carbohydrate metabolism resulting from insulin resistance leads to hyperglycemia, the hallmark of type 2 diabetes mellitus (T2DM). While pharmacological activation of AMPK is anticipated to improve these parameters, the discovery of selective, direct activators has proven challenging.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C22R05B09

QC Data

View QC data: current batch, Lot# C22R05B09

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

MK-3903 is a potent and selective AMP-activated protein kinase (AMPK) activator with an EC50 of 8 nM.

In vitro activity:

pcDNA3.1-MK-3903 plasmid was transfected to SGC7901/5-FU cells with TRIM14 silence. The overexpression of MK-3903 reversed the inhibiting role of TRIM14 knockout on the proliferation and autophagy of SGC7901/5-FU cells. Reference: Drug Dev Res. 2020 Aug;81(5):544-550. https://pubmed.ncbi.nlm.nih.gov/32096264/

In vivo activity:

A hit-to-lead effort resulting in the discovery of a potent and selective class of benzimidazole-based direct AMPK activators, exemplified by 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid, 42 (MK-3903) has been described. MK-3903 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice. Reference: J Med Chem. 2017 Nov 9;60(21):9040-9052. https://pubmed.ncbi.nlm.nih.gov/29035567/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	219.83

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 454.91 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:

1. Xiao F, Ouyang B, Zou J, Yang Y, Yi L, Yan H. Trim14 promotes autophagy and chemotherapy resistance of gastric cancer cells by regulating AMPK/mTOR pathway. Drug Dev Res. 2020 Aug;81(5):544-550. doi: 10.1002/ddr.21650. Epub 2020 Feb 25. PMID: 32096264. 2. Zhang H, Chi M, Chen L, Sun X, Wan L, Yang Q, Guo C. Daidzein alleviates cisplatin-induced muscle atrophy by regulating Glut4/AMPK/FoxO pathway. Phytother Res. 2021 Aug;35(8):4363-4376. doi: 10.1002/ptr.7132. Epub 2021 Apr 20. PMID: 33876509. 3. Lan P, Romero FA, Wodka D, Kassick AJ, Dang Q, Gibson T, Cashion D, Zhou G, Chen Y, Zhang X, Zhang A, Li Y, Trujillo ME, Shao Q, Wu M, Xu S, He H, MacKenna D, Staunton J, Chapman KT, Weber A, Sebhat IK, Makara GM. Hit-to-Lead Optimization and Discovery of 5-((5-([1,1'-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase. J Med Chem. 2017 Nov 9;60(21):9040-9052. doi: 10.1021/acs.jmedchem.7b01344. Epub 2017 Oct 25. PMID: 29035567.

In vitro protocol:

In vivo protocol:

1. Zhang H, Chi M, Chen L, Sun X, Wan L, Yang Q, Guo C. Daidzein alleviates cisplatin-induced muscle atrophy by regulating Glut4/AMPK/FoxO pathway. Phytother Res. 2021 Aug;35(8):4363-4376. doi: 10.1002/ptr.7132. Epub 2021 Apr 20. PMID: 33876509. 2. Lan P, Romero FA, Wodka D, Kassick AJ, Dang Q, Gibson T, Cashion D, Zhou G, Chen Y, Zhang X, Zhang A, Li Y, Trujillo ME, Shao Q, Wu M, Xu S, He H, MacKenna D, Staunton J, Chapman KT, Weber A, Sebhat IK, Makara GM. Hit-to-Lead Optimization and Discovery of 5-((5-([1,1'-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase. J Med Chem. 2017 Nov 9;60(21):9040-9052. doi: 10.1021/acs.jmedchem.7b01344. Epub 2017 Oct 25. PMID: 29035567.

Hit-to-Lead Optimization and Discovery of 5-((5-([1,1′-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase Ping Lan, F. Anthony Romero, Dariusz Wodka, Andrew J. Kassick, Qun Dang, Tony Gibson, Daniel Cashion, Gaochao Zhou, Yuli Chen, Xiaoping Zhang, Aihua Zhang, Ying Li, Maria E. Trujillo, Qing Shao, Margaret Wu, Shiyao Xu, Huaibing He, Deidre MacKenna, Jocelyn Staunton, Kevin T. Chapman, Ann Weber, Iyassu K. Sebhat, and Gergely M. Makara Publication Date (Web): October 16, 2017 (Article) DOI: 10.1021/acs.jmedchem.7b01344