Ceralasertib formate

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MedKoo CAT#: 528901

CAS#: 1352280-98-8 (formic acid)

Description: Ceralasertib, also known as AZD6738, is an orally available morpholino-pyrimidine-based inhibitor of ataxia telangiectasia and rad3 related (ATR) kinase, with potential antineoplastic activity. Upon oral administration, ATR kinase inhibitor Ceralasertib selectively inhibits ATR activity by blocking the downstream phosphorylation of the serine/threonine protein kinase CHK1. This prevents ATR-mediated signaling, and results in the inhibition of DNA damage checkpoint activation, disruption of DNA damage repair, and the induction of tumor cell apoptosis.


Price and Availability

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Pricing updated 2020-07-14. Prices are subject to change without notice.

Ceralasertib formate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528901
Name: Ceralasertib formate
CAS#: 1352280-98-8 (formic acid)
Chemical Formula: C21H26N6O4S
Exact Mass:
Molecular Weight: 458.537
Elemental Analysis: C, 55.01; H, 5.72; N, 18.33; O, 13.96; S, 6.99


Related CAS #: 1352226-88-0 (free base)   1352280-98-8 (formic acid)   1352226-97-1 (racemic)    

Synonym: Ceralasertib formate; Ceralasertib; AZD-6738; AZD6738; AZD 6738;

IUPAC/Chemical Name: 4-[4-[1-[[S(R)]-S-Methylsulfonimidoyl]cyclopropyl]-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinyl]-1H-pyrrolo[2,3-b]pyridine, formic acid

InChi Key: JOKLXYXIZOXQHY-FQAMYIAXSA-N

InChi Code: InChI=1S/C20H24N6O2S.CH2O2/c1-13-12-28-10-9-26(13)17-11-16(20(5-6-20)29(2,21)27)24-19(25-17)15-4-8-23-18-14(15)3-7-22-18;2-1-3/h3-4,7-8,11,13,21H,5-6,9-10,12H2,1-2H3,(H,22,23);1H,(H,2,3)/t13-,29-;/m1./s1

SMILES Code: C[C@H]1N(C2=CC(C3([S@@](=N)(C)=O)CC3)=NC(C4=C5C(NC=C5)=NC=C4)=N2)CCOC1.O=CO


Technical Data

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:
>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:
2934.99.9001


References

1: Min A, Im SA, Jang H, Kim S, Lee M, Kim DK, Yang Y, Kim HJ, Lee KH, Kim JW, Kim TY, Oh DY, Brown J, Lau A, O Connor MJ, Bang YJ. AZD6738, a novel oral inhibitor of ATR, induces synthetic lethality with ATM-deficiency in gastric cancer cells. Mol Cancer Ther. 2017 Jan 30. pii: molcanther.0378.2016. doi: 10.1158/1535-7163.MCT-16-0378. [Epub ahead of print] PubMed PMID: 28138034.

2: Vendetti FP, Lau A, Schamus S, Conrads TP, O'Connor MJ, Bakkenist CJ. The orally active and bioavailable ATR kinase inhibitor AZD6738 potentiates the anti-tumor effects of cisplatin to resolve ATM-deficient non-small cell lung cancer in vivo. Oncotarget. 2015 Dec 29;6(42):44289-305. doi: 10.18632/oncotarget.6247. PubMed PMID: 26517239; PubMed Central PMCID: PMC4792557.

3: Kim HJ, Min A, Im SA, Jang H, Lee KH, Lau A, Lee M, Kim S, Yang Y, Kim J, Kim TY, Oh DY, Brown J, O'Connor MJ, Bang YJ. Anti-tumor activity of the ATR inhibitor AZD6738 in HER2 positive breast cancer cells. Int J Cancer. 2017 Jan 1;140(1):109-119. doi: 10.1002/ijc.30373. PubMed PMID: 27501113.

4: Dillon MT, Barker HE, Pedersen M, Hafsi H, Bhide SA, Newbold KL, Nutting CM, McLaughlin M, Harrington KJ. Radiosensitization by the ATR Inhibitor AZD6738 through Generation of Acentric Micronuclei. Mol Cancer Ther. 2017 Jan;16(1):25-34. doi: 10.1158/1535-7163.MCT-16-0239. PubMed PMID: 28062704; PubMed Central PMCID: PMC5302142.

5: Kiesel BF, Shogan JC, Rachid M, Parise RA, Vendetti FP, Bakkenist CJ, Beumer JH. LC-MS/MS assay for the simultaneous quantitation of the ATM inhibitor AZ31 and the ATR inhibitor AZD6738 in mouse plasma. J Pharm Biomed Anal. 2017 May 10;138:158-165. doi: 10.1016/j.jpba.2017.01.055. PubMed PMID: 28213176; PubMed Central PMCID: PMC5357441.

6: Checkley S, MacCallum L, Yates J, Jasper P, Luo H, Tolsma J, Bendtsen C. Bridging the gap between in vitro and in vivo: Dose and schedule predictions for the ATR inhibitor AZD6738. Sci Rep. 2015 Aug 27;5:13545. doi: 10.1038/srep13545. Erratum in: Sci Rep. 2016;6:16545. PubMed PMID: 26310312; PubMed Central PMCID: PMC4550834.

7: Checkley S, MacCallum L, Yates J, Jasper P, Luo H, Tolsma J, Bendtsen C. Corrigendum: Bridging the gap between in vitro and in vivo: Dose and schedule predictions for the ATR inhibitor AZD6738. Sci Rep. 2016 Feb 9;6:16545. doi: 10.1038/srep16545. PubMed PMID: 26859465; PubMed Central PMCID: PMC4747154.

8: Kwok M, Davies N, Agathanggelou A, Smith E, Petermann E, Yates E, Brown J, Lau A, Stankovic T. Synthetic lethality in chronic lymphocytic leukaemia with DNA damage response defects by targeting the ATR pathway. Lancet. 2015 Feb 26;385 Suppl 1:S58. doi: 10.1016/S0140-6736(15)60373-7. PubMed PMID: 26312880.

9: Kwok M, Davies N, Agathanggelou A, Smith E, Oldreive C, Petermann E, Stewart G, Brown J, Lau A, Pratt G, Parry H, Taylor M, Moss P, Hillmen P, Stankovic T. ATR inhibition induces synthetic lethality and overcomes chemoresistance in TP53- or ATM-defective chronic lymphocytic leukemia cells. Blood. 2016 Feb 4;127(5):582-95. doi: 10.1182/blood-2015-05-644872. PubMed PMID: 26563132.

10: Biskup E, Naym DG, Gniadecki R. Small-molecule inhibitors of Ataxia Telangiectasia and Rad3 related kinase (ATR) sensitize lymphoma cells to UVA radiation. J Dermatol Sci. 2016 Dec;84(3):239-247. doi: 10.1016/j.jdermsci.2016.09.010. PubMed PMID: 27743911.

11: Ma J, Li X, Su Y, Zhao J, Luedtke DA, Epshteyn V, Edwards H, Wang G, Wang Z, Chu R, Taub JW, Lin H, Wang Y, Ge Y. Mechanisms responsible for the synergistic antileukemic interactions between ATR inhibition and cytarabine in acute myeloid leukemia cells. Sci Rep. 2017 Feb 8;7:41950. doi: 10.1038/srep41950. PubMed PMID: 28176818; PubMed Central PMCID: PMC5296912.

12: Vendetti FP, Leibowitz BJ, Barnes J, Schamus S, Kiesel BF, Abberbock S, Conrads T, Clump DA, Cadogan E, O'Connor MJ, Yu J, Beumer JH, Bakkenist CJ. Pharmacologic ATM but not ATR kinase inhibition abrogates p21-dependent G1 arrest and promotes gastrointestinal syndrome after total body irradiation. Sci Rep. 2017 Feb 1;7:41892. doi: 10.1038/srep41892. PubMed PMID: 28145510; PubMed Central PMCID: PMC5286430.

13: Kim H, George E, Ragland RL, Rafail S, Zhang R, Krepler C, Morgan M, Herlyn M, Brown EJ, Simpkins F. Targeting the ATR/CHK1 axis with PARP inhibition results in tumor regression in BRCA mutant ovarian cancer models. Clin Cancer Res. 2016 Dec 19. pii: clincanres.2273.2016. [Epub ahead of print] PubMed PMID: 27993965.

14: Karnitz LM, Zou L. Molecular Pathways: Targeting ATR in Cancer Therapy. Clin Cancer Res. 2015 Nov 1;21(21):4780-5. doi: 10.1158/1078-0432.CCR-15-0479. Review. PubMed PMID: 26362996; PubMed Central PMCID: PMC4631635.

15: Foote KM, Lau A, Nissink JW. Drugging ATR: progress in the development of specific inhibitors for the treatment of cancer. Future Med Chem. 2015;7(7):873-91. doi: 10.4155/fmc.15.33. Review. PubMed PMID: 26061106.