ABT-751
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MedKoo CAT#: 200050

CAS#: 141430-65-1 (free base)

Description: ABT-751, also known as E7010, is an orally bioavailable antimitotic sulfonamide. ABT-751 binds to the colchicine-binding site on beta-tubulin and inhibits the polymerization of microtubules, thereby preventing tumor cell replication. This agent also disrupts tumor neovascularization, reducing tumor blood flow and so inducing a cytotoxic effect.


Chemical Structure

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ABT-751
CAS# 141430-65-1 (free base)

Theoretical Analysis

MedKoo Cat#: 200050
Name: ABT-751
CAS#: 141430-65-1 (free base)
Chemical Formula: C18H17N3O4S
Exact Mass: 371.09398
Molecular Weight: 371.41
Elemental Analysis: C, 58.21; H, 4.61; N, 11.31; O, 17.23; S, 8.63

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 Same Day
50.0mg USD 250.0 Same Day
100.0mg USD 450.0 Same Day
200.0mg USD 650.0 Same Day
500.0mg USD 950.0 Same Day
1.0g USD 1450.0 Same Day
2.0g USD 2450.0 Same day
5.0g USD 4250.0 2 Weeks
10.0g USD 6950.0 2 Weeks
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Related CAS #: 141430-65-1 (free base)   857447-92-8   141450-48-8 (HCl)    

Synonym: ABT751; ABT-751; ABT 751; E 7010; E-7010; E7010

IUPAC/Chemical Name: N-(2-((4-hydroxyphenyl)amino)pyridin-3-yl)-4-methoxybenzenesulfonamide

InChi Key: URCVCIZFVQDVPM-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H17N3O4S/c1-25-15-8-10-16(11-9-15)26(23,24)21-17-3-2-12-19-18(17)20-13-4-6-14(22)7-5-13/h2-12,21-22H,1H3,(H,19,20)

SMILES Code: O=S(C1=CC=C(OC)C=C1)(NC2=CC=CN=C2NC3=CC=C(O)C=C3)=O

Appearance: Pink Solid

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, not in water

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: 2935009090

Biological target: ABT-751 (E7010) is a tubulin-binding and antimitotic sulfonamide agent with IC50s of ~ 1.5 and 3.4 μM in neuroblastoma and non-neuroblastoma cell lines, respectively.
In vitro activity: The upstream mechanisms of apoptosis which were triggered by a novel anti-microtubule drug, ABT-751, were investigated in hepatocellular carcinoma-derived Huh-7 cells. ABT-751 caused dysregulation of microtubule, collapse of mitochondrial membrane potential, generation of reactive oxygen species (ROS), DNA damage, G2/M cell cycle arrest, inhibition of anchorage-independent cell growth and apoptosis in Huh-7 cells. ABT-751 also induced early autophagy via upregulation of nuclear TP53 and downregulation of the AKT serine/threonine kinase (AKT)/mechanistic target of rapamycin (MTOR) pathway. Through modulation of the expression levels of DNA damage checkpoint proteins and G2/M cell cycle regulators, ABT-751 induced G2/M cell cycle arrest. Subsequently, ABT-751 triggered apoptosis with marked downregulation of B-cell CLL/lymphoma 2, upregulation of mitochondrial BCL2 antagonist/killer 1 and BCL2 like 11 protein levels, and cleavages of caspase 8 (CASP8), CASP9, CASP3 and DNA fragmentation factor subunit alpha proteins. Reference: Toxicol Appl Pharmacol. 2016 Nov 15;311:88-98. https://www.sciencedirect.com/science/article/abs/pii/S0041008X16302873?via%3Dihub
In vivo activity: The antivascular properties of ABT-751 were investigated in a rat subcutaneous tumor model using dynamic contrast-enhanced magnetic resonance imaging. A single dose of ABT-751 (30 mg/kg, intravenously) induced a rapid, transient reduction in tumor perfusion. After 1 h, tumor perfusion decreased by 57% before recovering to near pretreatment levels within 6 h. In contrast, ABT-751 produced little change in muscle perfusion at either time point. Reference: Anticancer Drugs. 2009 Jul;20(6):483-92. https://journals.lww.com/anti-cancerdrugs/Abstract/2009/07000/ABT_751,_a_novel_tubulin_binding_agent,_decreases.10.aspx

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 53.05 142.83
Ethanol 10.65 28.67

Preparing Stock Solutions

The following data is based on the product molecular weight 371.41 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. Wei RJ, Lin SS, Wu WR, Chen LR, Li CF, Chen HD, Chou CT, Chen YC, Liang SS, Chien ST, Shiue YL. A microtubule inhibitor, ABT-751, induces autophagy and delays apoptosis in Huh-7 cells. Toxicol Appl Pharmacol. 2016 Nov 15;311:88-98. doi: 10.1016/j.taap.2016.09.021. Epub 2016 Sep 24. PMID: 27678524. 2. Dehghanian SZ, Pan CT, Lee JM, Shiue YL. ABT-751 Induces Multiple Anticancer Effects in Urinary Bladder Urothelial Carcinoma-Derived Cells: Highlighting the Induction of Cytostasis through the Inhibition of SKP2 at Both Transcriptional and Post-Translational Levels. Int J Mol Sci. 2021 Jan 19;22(2):945. doi: 10.3390/ijms22020945. PMID: 33478005; PMCID: PMC7835924. 3. Luo Y, Hradil VP, Frost DJ, Rosenberg SH, Gordon GB, Morgan SJ, Gagne GD, Cox BF, Tahir SK, Fox GB. ABT-751, a novel tubulin-binding agent, decreases tumor perfusion and disrupts tumor vasculature. Anticancer Drugs. 2009 Jul;20(6):483-92. doi: 10.1097/CAD.0b013e32832c0acf. PMID: 19398903.
In vitro protocol: 1. Wei RJ, Lin SS, Wu WR, Chen LR, Li CF, Chen HD, Chou CT, Chen YC, Liang SS, Chien ST, Shiue YL. A microtubule inhibitor, ABT-751, induces autophagy and delays apoptosis in Huh-7 cells. Toxicol Appl Pharmacol. 2016 Nov 15;311:88-98. doi: 10.1016/j.taap.2016.09.021. Epub 2016 Sep 24. PMID: 27678524. 2. Dehghanian SZ, Pan CT, Lee JM, Shiue YL. ABT-751 Induces Multiple Anticancer Effects in Urinary Bladder Urothelial Carcinoma-Derived Cells: Highlighting the Induction of Cytostasis through the Inhibition of SKP2 at Both Transcriptional and Post-Translational Levels. Int J Mol Sci. 2021 Jan 19;22(2):945. doi: 10.3390/ijms22020945. PMID: 33478005; PMCID: PMC7835924.
In vivo protocol: 1. Luo Y, Hradil VP, Frost DJ, Rosenberg SH, Gordon GB, Morgan SJ, Gagne GD, Cox BF, Tahir SK, Fox GB. ABT-751, a novel tubulin-binding agent, decreases tumor perfusion and disrupts tumor vasculature. Anticancer Drugs. 2009 Jul;20(6):483-92. doi: 10.1097/CAD.0b013e32832c0acf. PMID: 19398903.

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1: Fox E, Mosse' YP, Meany HM, Gurney JG, Khanna G, Jackson HA, Gordon G, Shusterman S, Park JR, Cohn SL, Adamson PC, London WB, Maris JM, Balis FM. Time to disease progression in children with relapsed or refractory neuroblastoma treated with ABT-751: a report from the Children's Oncology Group (ANBL0621). Pediatr Blood Cancer. 2014 Jun;61(6):990-6. doi: 10.1002/pbc.24900. Epub 2013 Dec 18. PubMed PMID: 24347462.

2: Innocenti F, Ramírez J, Obel J, Xiong J, Mirkov S, Chiu YL, Katz DA, Carr RA, Zhang W, Das S, Adjei A, Moyer AM, Chen PX, Krivoshik A, Medina D, Gordon GB, Ratain MJ, Sahelijo L, Weinshilboum RM, Fleming GF, Bhathena A. Preclinical discovery of candidate genes to guide pharmacogenetics during phase I development: the example of the novel anticancer agent ABT-751. Pharmacogenet Genomics. 2013 Jul;23(7):374-81. doi: 10.1097/FPC.0b013e3283623e81. PubMed PMID: 23670235; PubMed Central PMCID: PMC3858967.

3: Ma T, Fuld AD, Rigas JR, Hagey AE, Gordon GB, Dmitrovsky E, Dragnev KH. A phase I trial and in vitro studies combining ABT-751 with carboplatin in previously treated non-small cell lung cancer patients. Chemotherapy. 2012;58(4):321-9. doi: 10.1159/000343165. Epub 2012 Nov 12. PubMed PMID: 23147218; PubMed Central PMCID: PMC3570826.

4: Gaynon PS, Harned TM; Therapeutic Advances in Childhood Leukemia/Lymphoma Consortium. ABT-751 in relapsed childhood acute lymphoblastic leukemia. J Pediatr Hematol Oncol. 2012 Oct;34(7):583-4. PubMed PMID: 22584778.

5: Silver M, Rusk A, Phillips B, Beck E, Jankowski M, Philibert J, Hahn K, Hershey E, McKeegan E, Bauch J, Krivoshik A, Khanna C. Evaluation of the oral antimitotic agent (ABT-751) in dogs with lymphoma. J Vet Intern Med. 2012 Mar-Apr;26(2):349-54. doi: 10.1111/j.1939-1676.2012.00892.x. Epub 2012 Feb 28. PubMed PMID: 22369215.

6: Rudin CM, Mauer A, Smakal M, Juergens R, Spelda S, Wertheim M, Coates A, McKeegan E, Ansell P, Zhou X, Qian J, Pradhan R, Dowell B, Krivoshik A, Gordon G. Phase I/II study of pemetrexed with or without ABT-751 in advanced or metastatic non-small-cell lung cancer. J Clin Oncol. 2011 Mar 10;29(8):1075-82. doi: 10.1200/JCO.2010.32.5944. Epub 2011 Feb 7. PubMed PMID: 21300929.

7: Fox E, Maris JM, Cohn SL, Goodspeed W, Goodwin A, Kromplewski M, Medina D, Xiong H, Krivoshik A, Widemann B, Adamson PC, Balis FM. Pharmacokinetics of orally administered ABT-751 in children with neuroblastoma and other solid tumors. Cancer Chemother Pharmacol. 2010 Sep;66(4):737-43. doi: 10.1007/s00280-009-1218-z. Epub 2010 Jan 1. PubMed PMID: 20044751.

8: Meany HJ, Sackett DL, Maris JM, Ward Y, Krivoshik A, Cohn SL, Steinberg SM, Balis FM, Fox E. Clinical outcome in children with recurrent neuroblastoma treated with ABT-751 and effect of ABT-751 on proliferation of neuroblastoma cell lines and on tubulin polymerization in vitro. Pediatr Blood Cancer. 2010 Jan;54(1):47-54. doi: 10.1002/pbc.22267. PubMed PMID: 19731320; PubMed Central PMCID: PMC2783914.

9: Michels J, Ellard SL, Le L, Kollmannsberger C, Murray N, Tomlinson Guns ES, Carr R, Chi KN. A phase IB study of ABT-751 in combination with docetaxel in patients with advanced castration-resistant prostate cancer. Ann Oncol. 2010 Feb;21(2):305-11. doi: 10.1093/annonc/mdp311. Epub 2009 Jul 24. PubMed PMID: 19633045.

10: Luo Y, Hradil VP, Frost DJ, Rosenberg SH, Gordon GB, Morgan SJ, Gagne GD, Cox BF, Tahir SK, Fox GB. ABT-751, a novel tubulin-binding agent, decreases tumor perfusion and disrupts tumor vasculature. Anticancer Drugs. 2009 Jul;20(6):483-92. doi: 10.1097/CAD.0b013e32832c0acf. PubMed PMID: 19398903.

ABT-751

25.0mg / USD 150.0


Additional Information

Related CAS#
141430-65-1 (ABT-751)
857447-92-8 (previous assigned for ABT-751 's CAS#, it was deleted now)