ASP4132 tosylate
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MedKoo CAT#: 207128

CAS#: 1640294-30-9 (tosylate)

Description: ASP4132 is an AMPK activator with potential antineoplastic activity. Upon oral administration, ASP4132 affects oxidative phosphorylation in mitochondria of metabolically-active tumor cells, which reduces both energy production and tumor cell proliferation. Mitochondrial oxidative phosphorylation is hyperactivated in tumor cells and plays a key role in the promotion of tumor cell proliferation.

Chemical Structure

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ASP4132 tosylate
CAS# 1640294-30-9 (tosylate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 207128
Name: ASP4132 tosylate
CAS#: 1640294-30-9 (tosylate)
Chemical Formula: C46H51F3N6O8S2
Exact Mass: 0.00
Molecular Weight: 937.063
Elemental Analysis: C, 58.96; H, 5.49; F, 6.08; N, 8.97; O, 13.66; S, 6.84

Price and Availability

Size Price Availability Quantity
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 1950 2 Weeks
500mg USD 3650 2 Weeks
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Related CAS #: 1640294-29-6 (free base)   1640294-30-9 (tosylate)    

Synonym: ASP4132 tosylate; ASP 4132; ASP-4132; ASP4132

IUPAC/Chemical Name: (6-(1-((6-methoxypyridin-3-yl)methyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-yl)(4-(4-(trifluoromethyl)benzyl)piperazin-1-yl)methanone bis(4-methylbenzenesulfonate)

InChi Key: KDMGCEXVMOJAAC-UHFFFAOYSA-N

InChi Code: InChI=1S/C32H35F3N6O2.2C7H8O3S/c1-43-29-9-4-23(19-36-29)21-39-12-10-24(11-13-39)25-5-8-27-28(18-25)38-30(37-27)31(42)41-16-14-40(15-17-41)20-22-2-6-26(7-3-22)32(33,34)35;2*1-6-2-4-7(5-3-6)11(8,9)10/h2-9,18-19,24H,10-17,20-21H2,1H3,(H,37,38);2*2-5H,1H3,(H,8,9,10)

SMILES Code: O=C(C1=NC2=CC=C(C3CCN(CC4=CC=C(OC)N=C4)CC3)C=C2N1)N5CCN(CC6=CC=C(C(F)(F)F)C=C6)CC5.OS(=O)(C7=CC=C(C)C=C7)=O.OS(=O)(C8=CC=C(C)C=C8)=O

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: ASP4132 is an orally active, potent AMPK activator with an EC50 of 18 nM.
In vitro activity: The resulting in vitro pharmacological properties and aqueous solubility of 28 (ASP4132 tosylate) are summarized in Table 9. Compound 28 showed comparable cell growth inhibitory (IC50 = 0.014 μM) activity against MDA-MB-453 to that of compound 2. Furthermore, 28 showed relatively weak antiproliferative activity against SK-BR-3 (IC50 > 3 μM), indicating that the selectivity of cellular growth inhibitory activity observed in lead compound 2 was maintained in 28. In addition, the aqueous solubility of 28 was significantly higher than that of 2, especially in the Japanese Pharmacopoeia 2nd fluid for disintegration test (JP2: pH = 6.8) with taurocholic acid. Reference: Bioorg Med Chem. 2020 Mar 1;28(5):115307. https://pubmed.ncbi.nlm.nih.gov/32007387/
In vivo activity: By recording tumor volumes this study found that oral administration of a single dose of ASP4132 (5 mg/kg body weight, for 21 days) largely inhibited NSCLC xenograft growth in SCID mice (Fig. 6A). This concentration was based on the recommendation from the supplier. Volumes of NSCLC xenografts with ASP4132 administration were significantly lower than those of vehicle control xenografts (Fig. 6A). Results showed that ASP4132 oral administration potently suppressed NSCLC xenograft growth in SCID mice (Fig. 6B). At Day-42 all tumors of the two groups were separated through surgery and weighted individually. Results in Fig. 6C demonstrated that ASP4132-treated NSCLC xenografts were dramatically lighter than the control tumors. Importantly, the mice body weights were not significantly different between the ASP4132 group and vehicle control group (Fig. 6D), indicating that mice should be well-tolerated to ASP4132 treatment regimen, and this study did not detect any apparent toxicities. Reference: Cell Death Dis. 2021 Apr; 12(4): 365. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8024326/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 175.0 186.75

Preparing Stock Solutions

The following data is based on the product molecular weight 937.06 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. Xia YC, Zha JH, Sang YH, Yin H, Xu GQ, Zhen J, Zhang Y, Yu BT. AMPK activation by ASP4132 inhibits non-small cell lung cancer cell growth. Cell Death Dis. 2021 Apr 6;12(4):365. doi: 10.1038/s41419-021-03655-2. PMID: 33824293; PMCID: PMC8024326. 2. Kuramoto K, Yamada H, Shin T, Sawada Y, Azami H, Yamada T, Nagashima T, Ohnuki K. Development of a potent and orally active activator of adenosine monophosphate-activated protein kinase (AMPK), ASP4132, as a clinical candidate for the treatment of human cancer. Bioorg Med Chem. 2020 Mar 1;28(5):115307. doi: 10.1016/j.bmc.2020.115307. Epub 2020 Jan 8. PMID: 32007387.
In vitro protocol: 1. Xia YC, Zha JH, Sang YH, Yin H, Xu GQ, Zhen J, Zhang Y, Yu BT. AMPK activation by ASP4132 inhibits non-small cell lung cancer cell growth. Cell Death Dis. 2021 Apr 6;12(4):365. doi: 10.1038/s41419-021-03655-2. PMID: 33824293; PMCID: PMC8024326. 2. Kuramoto K, Yamada H, Shin T, Sawada Y, Azami H, Yamada T, Nagashima T, Ohnuki K. Development of a potent and orally active activator of adenosine monophosphate-activated protein kinase (AMPK), ASP4132, as a clinical candidate for the treatment of human cancer. Bioorg Med Chem. 2020 Mar 1;28(5):115307. doi: 10.1016/j.bmc.2020.115307. Epub 2020 Jan 8. PMID: 32007387.
In vivo protocol: 1. Xia YC, Zha JH, Sang YH, Yin H, Xu GQ, Zhen J, Zhang Y, Yu BT. AMPK activation by ASP4132 inhibits non-small cell lung cancer cell growth. Cell Death Dis. 2021 Apr 6;12(4):365. doi: 10.1038/s41419-021-03655-2. PMID: 33824293; PMCID: PMC8024326. 2. Kuramoto K, Yamada H, Shin T, Sawada Y, Azami H, Yamada T, Nagashima T, Ohnuki K. Development of a potent and orally active activator of adenosine monophosphate-activated protein kinase (AMPK), ASP4132, as a clinical candidate for the treatment of human cancer. Bioorg Med Chem. 2020 Mar 1;28(5):115307. doi: 10.1016/j.bmc.2020.115307. Epub 2020 Jan 8. PMID: 32007387.

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Kuramoto K, Yamada H, Shin T, et al. Development of a potent and orally active activator of adenosine monophosphate-activated protein kinase (AMPK), ASP4132, as a clinical candidate for the treatment of human cancer. Bioorg Med Chem. 2020;28(5):115307. doi:10.1016/j.bmc.2020.115307