Barasertib
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MedKoo CAT#: 200420

CAS#: 722543-31-9 (free acid)

Description: Barasertib is an orally bioavailable, small-molecule, dihydrogen phosphate prodrug of the pyrazoloquinazoline Aurora kinase inhibitor AZD1152–hydroxyquinazoline pyrazol anilide (AZD1152-HQPA) with potential antineoplastic activity. Upon administration and rapid conversion from the prodrug form in plasma, barasertib specifically binds to and inhibits Aurora kinase B, which results in the disruption of spindle checkpoint functions and chromosome alignment and, so, the disruption of chromosome segregation and cytokinesis. Consequently, cell division and cell proliferation are inhibited and apoptosis is induced in Aurora kinase B-overexpressing tumor cells. IMPORTANT NOTE: AZD-1152HQPA IS NOT AZD-1152 or Barasertib. Many vendors are selling Barasertib with the wrong structure.


Chemical Structure

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Barasertib
CAS# 722543-31-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 200420
Name: Barasertib
CAS#: 722543-31-9 (free acid)
Chemical Formula: C26H31FN7O6P
Exact Mass: 587.21
Molecular Weight: 587.540
Elemental Analysis: C, 53.15; H, 5.32; F, 3.23; N, 16.69; O, 16.34; P, 5.2 7

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1350 Ready to ship
500mg USD 2850 Ready to ship
1g USD 4650 Ready to ship
2g USD 7650 Ready to ship
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Related CAS #: 722543-31-9 (free acid)   722543-50-2 (2HCl)   957104-91-5 (maleate)  

Synonym: AZD1152; AZD-1152; AZD 1152; Barasertib.

IUPAC/Chemical Name: 2-(ethyl(3-(4-(5-(2-(3-fluorophenylamino)-2-oxoethyl)-1H-pyrazol-3-ylamino)quinazolin-7-yloxy)propyl)amino)ethyl dihydrogen phosphate

InChi Key: GBJVVSCPOBPEIT-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H31FN7O6P/c1-2-34(10-12-40-41(36,37)38)9-4-11-39-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(35)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17H,2,4,9-12,15H2,1H3,(H,30,35)(H2,36,37,38)(H2,28,29,31,32,33)

SMILES Code: O=P(O)(OCCN(CC)CCCOC1=CC2=NC=NC(NC3=NNC(CC(NC4=CC=CC(F)=C4)=O)=C3)=C2C=C1)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, not in water

Shelf Life: >5 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: 722543-50-2 (Barasertib or AZD-1152 dihydrochloride salt) 722543-31-9 (Barasertib or AZD-1152 free form) 722544-51-6 (AZD-1152-HQPA) Phase I study of  barasertib (AZD1152) .  barasertib (AZD1152) is a highly potent and selective Aurora B kinase inhibitor. The safety, efficacy and pharmacokinetic (PK) profile of barasertib were investigated in Japanese patients with advanced acute myeloid leukemia. Barasertib (50-1200mg) was administered as a continuous 7-day intravenous infusion every 21 days. No dose-limiting toxicities were reported and barasertib 1200mg was chosen for further evaluation in Japanese patients. Neutropenia and febrile neutropenia were the most commonly reported adverse events. The PK profile was similar to Western patients. A promising overall hematologic response rate of 19% was achieved, which warrants further investigation in these patients. (source: Leuk Res. 2011 Oct;35(10):1384-9. ).  .

Biological target: Barasertib (AZD1152) is an Aurora B inhibitor with an IC50 of 0.37 nM.
In vitro activity: Barasertib effectively reduced glucose uptake and lactate production in gastric cancer (GC) cells in a dose-dependent and time-dependent manner. The expression levels of GLUT1, LDHA and HK2 were decreased by barasertib treatment of GC cells. Furthermore, barasertib induced the expression of ribosomal protein S7 (RPS7), as a tumor suppressor, to regulate glucose metabolism. Reference: Anticancer Drugs. 2019 Jan;30(1):19-26. https://journals.lww.com/anti-cancerdrugs/Abstract/2019/01000/Aurora_kinase_B_inhibitor_barasertib__AZD1152_.2.aspx
In vivo activity: To test whether treatment with barasertib prevents the development of lung fibrosis, TGFα mice were concomitantly treated with Dox to induce TGFα expression and either barasertib (40 mg/kg body weight) or vehicle twice per day for 4 weeks (Fig 5A). Induction of TGFα caused extensive subpleural, perivascular, and peribronchial fibrosis (Fig 5B). TGFα‐activated mice that were concomitantly given barasertib showed reduced collagen staining with infrequent scattered small fibrotic areas. Further, there was a significant decrease in the lung weights and hydroxyproline levels in TGFα mice treated with barasertib compared to vehicle‐treated mice (Fig 5C and D). Together, these findings suggest that inhibition of AURKB activity by barasertib attenuates progressive fibrotic changes in TGFα mice. Reference: EMBO Mol Med. 2020 Sep 7;12(9):e12131. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7507328/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.0 56.17

Preparing Stock Solutions

The following data is based on the product molecular weight 587.54 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. He J, Qi Z, Zhang X, Yang Y, Liu F, Zhao G, Wang Z. Aurora kinase B inhibitor barasertib (AZD1152) inhibits glucose metabolism in gastric cancer cells. Anticancer Drugs. 2019 Jan;30(1):19-26. doi: 10.1097/CAD.0000000000000684. PMID: 30540594. 2. Kasam RK, Ghandikota S, Soundararajan D, Reddy GB, Huang SK, Jegga AG, Madala SK. Inhibition of Aurora Kinase B attenuates fibroblast activation and pulmonary fibrosis. EMBO Mol Med. 2020 Sep 7;12(9):e12131. doi: 10.15252/emmm.202012131. Epub 2020 Aug 6. PMID: 32761869; PMCID: PMC7507328.
In vitro protocol: 1. He J, Qi Z, Zhang X, Yang Y, Liu F, Zhao G, Wang Z. Aurora kinase B inhibitor barasertib (AZD1152) inhibits glucose metabolism in gastric cancer cells. Anticancer Drugs. 2019 Jan;30(1):19-26. doi: 10.1097/CAD.0000000000000684. PMID: 30540594.
In vivo protocol: 1. Kasam RK, Ghandikota S, Soundararajan D, Reddy GB, Huang SK, Jegga AG, Madala SK. Inhibition of Aurora Kinase B attenuates fibroblast activation and pulmonary fibrosis. EMBO Mol Med. 2020 Sep 7;12(9):e12131. doi: 10.15252/emmm.202012131. Epub 2020 Aug 6. PMID: 32761869; PMCID: PMC7507328.

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1: Garlapati C, Joshi S, Bhattarai S, Krishnamurthy J, Turaga RC, Nguyen T, Li X, Aneja R. PLK1 and AURKB phosphorylate survivin differentially to affect proliferation in racially distinct triple-negative breast cancer. Cell Death Dis. 2023 Jan 10;14(1):12. doi: 10.1038/s41419-022-05539-5. PMID: 36627281; PMCID: PMC9832024.


2: Bhutia WD, Gupta S, Rani R, Batra K, Sethi K, Kumar S, Kumar R. In vitro and in vivo evaluation of kinase and protease inhibitors against Trypanosoma evansi. Vet Res Commun. 2022 Jun 25. doi: 10.1007/s11259-022-09964-x. Epub ahead of print. PMID: 35751782.


3: Shimabukuro K, Fukazawa T, Kanai A, Kawai H, Mekata K, Hirohashi N, Kakimoto N, Tanimoto K. Low-Dose-Rate Irradiation Suppresses the Expression of Cell Cycle-Related Genes, Resulting in Modification of Sensitivity to Anti-Cancer Drugs. Cells. 2022 Jan 31;11(3):501. doi: 10.3390/cells11030501. PMID: 35159310; PMCID: PMC8833988.


4: Ivanova D, Zhelev Z, Zlateva G, Lazarova D, Yaneva Z, Panovska R, Aoki I, Bakalova R. Effect of Alpha-tocopheryl Succinate on the Cytotoxicity of Anticancer Drugs Towards Leukemia Lymphocytes. Anticancer Res. 2022 Jan;42(1):547-554. doi: 10.21873/anticanres.15512. PMID: 34969764.


5: McNeal AS, Belote RL, Zeng H, Urquijo M, Barker K, Torres R, Curtin M, Shain AH, Andtbacka RH, Holmen S, Lum DH, McCalmont TH, VanBrocklin MW, Grossman D, Wei ML, Lang UE, Judson-Torres RL. BRAFV600E induces reversible mitotic arrest in human melanocytes via microrna-mediated suppression of AURKB. Elife. 2021 Nov 23;10:e70385. doi: 10.7554/eLife.70385. PMID: 34812139; PMCID: PMC8610417.


6: Sankhe K, Prabhu A, Khan T. Design strategies, SAR, and mechanistic insight of Aurora kinase inhibitors in cancer. Chem Biol Drug Des. 2021 Jul;98(1):73-93. doi: 10.1111/cbdd.13850. Epub 2021 May 15. PMID: 33934503.


7: Borah NA, Sradhanjali S, Barik MR, Jha A, Tripathy D, Kaliki S, Rath S, Raghav SK, Patnaik S, Mittal R, Reddy MM. Aurora Kinase B Expression, Its Regulation and Therapeutic Targeting in Human Retinoblastoma. Invest Ophthalmol Vis Sci. 2021 Mar 1;62(3):16. doi: 10.1167/iovs.62.3.16. PMID: 33704359; PMCID: PMC7960835.


8: Shaalan AK, Teshima THN, Tucker AS, Proctor GB. Inhibition of Aurora Kinase B activity disrupts development and differentiation of salivary glands. Cell Death Discov. 2021 Jan 18;7(1):16. doi: 10.1038/s41420-020-00393-w. PMID: 33462217; PMCID: PMC7814035.


9: Bakalova R, Semkova S, Ivanova D, Zhelev Z, Miller T, Takeshima T, Shibata S, Lazarova D, Aoki I, Higashi T. Selective Targeting of Cancerous Mitochondria and Suppression of Tumor Growth Using Redox-Active Treatment Adjuvant. Oxid Med Cell Longev. 2020 Nov 2;2020:6212935. doi: 10.1155/2020/6212935. PMID: 33204397; PMCID: PMC7652615.


10: Wang Y, Yella JK, Ghandikota S, Cherukuri TC, Ediga HH, Madala SK, Jegga AG. Pan-transcriptome-based candidate therapeutic discovery for idiopathic pulmonary fibrosis. Ther Adv Respir Dis. 2020 Jan-Dec;14:1753466620971143. doi: 10.1177/1753466620971143. PMID: 33167785; PMCID: PMC7659024.


11: Kasam RK, Ghandikota S, Soundararajan D, Reddy GB, Huang SK, Jegga AG, Madala SK. Inhibition of Aurora Kinase B attenuates fibroblast activation and pulmonary fibrosis. EMBO Mol Med. 2020 Sep 7;12(9):e12131. doi: 10.15252/emmm.202012131. Epub 2020 Aug 6. PMID: 32761869; PMCID: PMC7507328.


12: Lakkaniga NR, Zhang L, Belachew B, Gunaganti N, Frett B, Li HY. Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression. Eur J Med Chem. 2020 Oct 1;203:112589. doi: 10.1016/j.ejmech.2020.112589. Epub 2020 Jul 12. PMID: 32717530.


13: Goto H, Yoshino Y, Ito M, Nagai J, Kumamoto T, Inukai T, Sakurai Y, Miyagawa N, Keino D, Yokosuka T, Iwasaki F, Hamanoue S, Shiomi M, Goto S. Aurora B kinase as a therapeutic target in acute lymphoblastic leukemia. Cancer Chemother Pharmacol. 2020 Apr;85(4):773-783. doi: 10.1007/s00280-020-04045-9. Epub 2020 Mar 6. Erratum in: Cancer Chemother Pharmacol. 2021 Dec;88(6):1055-1056. PMID: 32144432.


14: Zhang J, Lin X, Wu L, Huang JJ, Jiang WQ, Kipps TJ, Zhang S. Aurora B induces epithelial-mesenchymal transition by stabilizing Snail1 to promote basal-like breast cancer metastasis. Oncogene. 2020 Mar;39(12):2550-2567. doi: 10.1038/s41388-020-1165-z. Epub 2020 Jan 29. PMID: 31996785.


15: Shaalan A, Proctor G. Salivary glands require Aurora Kinase B for regeneration after transient innate immune-mediated injury. Sci Rep. 2019 Aug 5;9(1):11339. doi: 10.1038/s41598-019-47762-9. PMID: 31383943; PMCID: PMC6683207.


16: Li J, Ha S, Li Z, Huang Y, Lin E, Xiao W. Aurora B prevents aneuploidy via MAD2 during the first mitotic cleavage in oxidatively damaged embryos. Cell Prolif. 2019 Sep;52(5):e12657. doi: 10.1111/cpr.12657. Epub 2019 Jul 1. PMID: 31264311; PMCID: PMC6797512.


17: Ivanova D, Zhelev Z, Semkova S, Aoki I, Bakalova R. Resveratrol Modulates the Redox-status and Cytotoxicity of Anticancer Drugs by Sensitizing Leukemic Lymphocytes and Protecting Normal Lymphocytes. Anticancer Res. 2019 Jul;39(7):3745-3755. doi: 10.21873/anticanres.13523. PMID: 31262901.


18: Sumi NJ, Ctortecka C, Hu Q, Bryant AT, Fang B, Remsing Rix LL, Ayaz M, Kinose F, Welsh EA, Eschrich SA, Lawrence HR, Koomen JM, Haura EB, Rix U. Divergent Polypharmacology-Driven Cellular Activity of Structurally Similar Multi-Kinase Inhibitors through Cumulative Effects on Individual Targets. Cell Chem Biol. 2019 Sep 19;26(9):1240-1252.e11. doi: 10.1016/j.chembiol.2019.06.003. Epub 2019 Jun 27. PMID: 31257184; PMCID: PMC6754293.


19: Qi J, Gao X, Zhong X, Zhang N, Wang R, Zhang H, Pan T, Liu X, Yao Y, Wu Q, Niu M, Xu K. Selective inhibition of Aurora A and B kinases effectively induces cell cycle arrest in t(8;21) acute myeloid leukemia. Biomed Pharmacother. 2019 Sep;117:109113. doi: 10.1016/j.biopha.2019.109113. Epub 2019 Jun 14. PMID: 31207577.


20: Bertran-Alamillo J, Cattan V, Schoumacher M, Codony-Servat J, Giménez- Capitán A, Cantero F, Burbridge M, Rodríguez S, Teixidó C, Roman R, Castellví J, García-Román S, Codony-Servat C, Viteri S, Cardona AF, Karachaliou N, Rosell R, Molina-Vila MA. AURKB as a target in non-small cell lung cancer with acquired resistance to anti-EGFR therapy. Nat Commun. 2019 Apr 18;10(1):1812. doi: 10.1038/s41467-019-09734-5. PMID: 31000705; PMCID: PMC6472415.