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MedKoo Cat#: 207082 | Name: Miransertib HCl
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Description:

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

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.

Chemical Structure

Miransertib HCl
Miransertib HCl
CAS#1313883-00-9 (HCl)

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

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to Ship
10mg USD 250.00 Ready to Ship
25mg USD 450.00 Ready to Ship
50mg USD 750.00 Ready to Ship
100mg USD 1,350.00 Ready to Ship
500mg USD 3,850.00 Ready to ship
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Related CAS #
1313881-70-7 (free base) 1313883-00-9 (HCl) 1817727-87-9 (3HCl) 1817727-88-0 (mesylate)
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
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
>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).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Miransertib hydrochloride (ARQ-092 hydrochloride) is an allosteric Akt inhibitor with IC50s of 2.7 nM, 14 nM and 8.1 nM for Akt1, Akt2, Akt3, respectively.
In vitro activity:
The expression levels of p-AKTT308 and p-AKTS473 were both significantly decreased after treated with any of the three compounds BYL719, ARQ092, and rapamycin. Compared with BYL719 or rapamycin, a lower dose of ARQ092 exhibited stronger inhibitory effects on decreasing phosphorylation of AKT at Thr308 and Ser473 (Fig. 4). These results suggested that ARQ092 could be considered as a potential medication measurement for CLOVES syndrome or other disorders caused by hyperactivation of the PI3K/AKT/mTOR pathway. Reference: Hereditas. 2021; 158: 18. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8170820/
In vivo activity:
For in vivo efficacy of Miransertib, groups of L. donovani infected BALB/c mice (seven days post infection with stationary phase promastigotes) were dosed daily, for five consecutive days per week with an oral formulation of Miransertib (50 and 75 mg/kg). On day 28 post-infection, the parasite burdens in the livers and spleens of infected mice were quantified. The only available FDA approved oral anti-leishmanial drug miltefosine (20 mg/kg, once daily, 5 days per week) was included as a positive control. Both Miransertib and miltefosine were well tolerated at both doses throughout the study, with no mice displaying any overt signs of toxicity. The results show that Miransertib effectively suppressed parasite burdens by 80–90% (Fig 3A and 3B). In fact, at 50 and 75 mg/kg, Miransertib effectively cured 50% of the study mice (2/4 mice in both treatment groups), with no detectable parasites in the livers and spleens. 50 and 75 mg/kg doses of Miransertib compared favorably with miltefosine in the spleen (Fig 3A), whereas it was more active than miltefosine in the liver (Fig 3B). These results show that Miransertib has potent anti-leishmanial activity in vivo against L. donovani. Reference: PLoS One. 2018 Nov 6;13(11):e0206920. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30399177/
Solvent mg/mL mM
Solubility
DMSO 75.0 159.92
Ethanol 4.0 8.53
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 468.99 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
Formulation protocol:
1. Yan W, Zhang B, Wang H, Mo R, Jiang X, Qin W, Ma L, Lin Z. Somatic frameshift mutation in PIK3CA causes CLOVES syndrome by provoking PI3K/AKT/mTOR pathway. Hereditas. 2021 Jun 1;158(1):18. doi: 10.1186/s41065-021-00184-y. PMID: 34074347; PMCID: PMC8170820. 2. 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. PMID: 29549527; PMCID: PMC5956072. 3. 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. PMID: 30399177; PMCID: PMC6219794. 4. 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. PMID: 28582432; PMCID: PMC5459472.
In vitro protocol:
1. Yan W, Zhang B, Wang H, Mo R, Jiang X, Qin W, Ma L, Lin Z. Somatic frameshift mutation in PIK3CA causes CLOVES syndrome by provoking PI3K/AKT/mTOR pathway. Hereditas. 2021 Jun 1;158(1):18. doi: 10.1186/s41065-021-00184-y. PMID: 34074347; PMCID: PMC8170820. 2. 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. PMID: 29549527; PMCID: PMC5956072.
In vivo protocol:
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. PMID: 30399177; PMCID: PMC6219794. 2. 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. PMID: 28582432; PMCID: PMC5459472.
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.