Miransertib HCl
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MedKoo CAT#: 207082

CAS#: 1313883-00-9 (HCl)

Description: Miransertib, also known as ARQ 092, is an oral activie, potent and selective AKT inhibitor with IC50 values: 5.0 nM (AKT1); 4.5 nM (AKT2); 16 nM (AKT3). ARQ 092 binds to and inhibits the activity of AKT in a non-ATP competitive manner, which may result in the inhibition of the PI3K/AKT signaling pathway. This may lead to the reduction in tumor cell proliferation and the induction of tumor cell apoptosis. ARQ-092 demonstrated high enzymatic potency against AKT1, AKT2, and AKT3, as well as potent cellular inhibition of AKT activation and the phosphorylation of the downstream target PRAS40. ARQ-092 also served as a potent inhibitor of the AKT1-E17K mutant protein and inhibited tumor growth in a human xenograft mouse model of endometrial adenocarcinoma.


Price and Availability

Size
Price

50mg
USD 250
500mg
USD 1650
5g
USD 7650
Size
Price

100mg
USD 450
1g
USD 2950
Size
Price

200mg
USD 850
2g
USD 4650

Miransertib HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 207082
Name: Miransertib HCl
CAS#: 1313883-00-9 (HCl)
Chemical Formula: C27H25ClN6
Exact Mass: 468.1829
Molecular Weight: 468.99
Elemental Analysis: C, 69.15; H, 5.37; Cl, 7.56; N, 17.92


Related CAS #: 1313881-70-7 (free base)   1313883-00-9 (HCl)   1817727-87-9 (3HCl)    

Synonym: Miransertib HCl; Miransertib hydrochloride; ARQ092; ARQ-092; ARQ 092 HCl;

IUPAC/Chemical Name: 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine hydrochloride

InChi Key: DRHSWSSVIKDJME-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H24N6.ClH/c28-24-21(8-4-17-30-24)25-32-23-14-13-22(18-6-2-1-3-7-18)31-26(23)33(25)20-11-9-19(10-12-20)27(29)15-5-16-27;/h1-4,6-14,17H,5,15-16,29H2,(H2,28,30);1H

SMILES Code: NC1=NC=CC=C1C2=NC3=CC=C(C4=CC=CC=C4)N=C3N2C5=CC=C(C6(N)CCC6)C=C5.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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:
>3 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).

Harmonized System Code:
2934990300


References

1: Nandan D, Zhang N, Yu Y, Schwartz B, Chen S, Kima PE, Reiner NE. Miransertib (ARQ 092), an orally-available, selective Akt inhibitor is effective against Leishmania. PLoS One. 2018 Nov 6;13(11):e0206920. doi: 10.1371/journal.pone.0206920. eCollection 2018. PubMed PMID: 30399177; PubMed Central PMCID: PMC6219794.

2: Bastian C, Quinn J, Tripathi A, Aquila D, McCray A, Dutta R, Baltan S, Brunet S. CK2 inhibition confers functional protection to young and aging axons against ischemia by differentially regulating the CDK5 and AKT signaling pathways. Neurobiol Dis. 2018 Jun 23. pii: S0969-9961(18)30149-9. doi: 10.1016/j.nbd.2018.05.011. [Epub ahead of print] PubMed PMID: 29944965.

3: Ranieri C, Di Tommaso S, Loconte DC, Grossi V, Sanese P, Bagnulo R, Susca FC, Forte G, Peserico A, De Luisi A, Bartuli A, Selicorni A, Melis D, Lerone M, Praticò AD, Abbadessa G, Yu Y, Schwartz B, Ruggieri M, Simone C, Resta N. In vitro efficacy of ARQ 092, an allosteric AKT inhibitor, on primary fibroblast cells derived from patients with PIK3CA-related overgrowth spectrum (PROS). Neurogenetics. 2018 May;19(2):77-91. doi: 10.1007/s10048-018-0540-1. Epub 2018 Mar 16. PubMed PMID: 29549527; PubMed Central PMCID: PMC5956072.

4: Jilkova ZM, Kuyucu AZ, Kurma K, Ahmad Pour ST, Roth GS, Abbadessa G, Yu Y, Schwartz B, Sturm N, Marche PN, Hainaut P, Decaens T. Combination of AKT inhibitor ARQ 092 and sorafenib potentiates inhibition of tumor progression in cirrhotic rat model of hepatocellular carcinoma. Oncotarget. 2018 Jan 23;9(13):11145-11158. doi: 10.18632/oncotarget.24298. eCollection 2018 Feb 16. PubMed PMID: 29541403; PubMed Central PMCID: PMC5834253.

5: Wang J, Chandrasekhar V, Abbadessa G, Yu Y, Schwartz B, Kontaridis MI. In vivo efficacy of the AKT inhibitor ARQ 092 in Noonan Syndrome with multiple lentigines-associated hypertrophic cardiomyopathy. PLoS One. 2017 Jun 5;12(6):e0178905. doi: 10.1371/journal.pone.0178905. eCollection 2017. PubMed PMID: 28582432; PubMed Central PMCID: PMC5459472.

6: Roth GS, Macek Jilkova Z, Zeybek Kuyucu A, Kurma K, Ahmad Pour ST, Abbadessa G, Yu Y, Busser B, Marche PN, Leroy V, Decaens T. Efficacy of AKT Inhibitor ARQ 092 Compared with Sorafenib in a Cirrhotic Rat Model with Hepatocellular Carcinoma. Mol Cancer Ther. 2017 Oct;16(10):2157-2165. doi: 10.1158/1535-7163.MCT-16-0602-T. Epub 2017 May 31. PubMed PMID: 28566435.

7: Yu Y, Hall T, Eathiraj S, Wick MJ, Schwartz B, Abbadessa G. In-vitro and in-vivo combined effect of ARQ 092, an AKT inhibitor, with ARQ 087, a FGFR inhibitor. Anticancer Drugs. 2017 Jun;28(5):503-513. doi: 10.1097/CAD.0000000000000486. PubMed PMID: 28240679; PubMed Central PMCID: PMC5404396.

8: Kim K, Li J, Barazia A, Tseng A, Youn SW, Abbadessa G, Yu Y, Schwartz B, Andrews RK, Gordeuk VR, Cho J. ARQ 092, an orally-available, selective AKT inhibitor, attenuates neutrophil-platelet interactions in sickle cell disease. Haematologica. 2017 Feb;102(2):246-259. doi: 10.3324/haematol.2016.151159. Epub 2016 Oct 6. PubMed PMID: 27758820; PubMed Central PMCID: PMC5286933.

9: Lapierre JM, Eathiraj S, Vensel D, Liu Y, Bull CO, Cornell-Kennon S, Iimura S, Kelleher EW, Kizer DE, Koerner S, Makhija S, Matsuda A, Moussa M, Namdev N, Savage RE, Szwaya J, Volckova E, Westlund N, Wu H, Schwartz B. Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin -2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor. J Med Chem. 2016 Jul 14;59(13):6455-69. doi: 10.1021/acs.jmedchem.6b00619. Epub 2016 Jun 29. PubMed PMID: 27305487.

10: Lindhurst MJ, Yourick MR, Yu Y, Savage RE, Ferrari D, Biesecker LG. Repression of AKT signaling by ARQ 092 in cells and tissues from patients with Proteus syndrome. Sci Rep. 2015 Dec 11;5:17162. doi: 10.1038/srep17162. PubMed PMID: 26657992; PubMed Central PMCID: PMC4675973.

11: Yu Y, Savage RE, Eathiraj S, Meade J, Wick MJ, Hall T, Abbadessa G, Schwartz B. Targeting AKT1-E17K and the PI3K/AKT Pathway with an Allosteric AKT Inhibitor, ARQ 092. PLoS One. 2015 Oct 15;10(10):e0140479. doi: 10.1371/journal.pone.0140479. eCollection 2015. PubMed PMID: 26469692; PubMed Central PMCID: PMC4607407.