Cediranib free base

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

Description:Cediranib, also known as AZD-2171, is a potent and selective VEGF inhibitor with antineoplastic activities. Competing with adenosine triphosphate, cediranib binds to and inhibits all three vascular endothelial growth factor receptor (VEGF-1,-2,-3) tyrosine kinases, thereby blocking VEGF-signaling, angiogenesis, and tumor cell growth.

Price and Availability

Cediranib free base,purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200690Name: Cediranib free baseCAS#: 288383-20-0 (free base)Chemical Formula: C25H27FN4O3Exact Mass: 450.20672Molecular Weight: 450.5Elemental Analysis: C, 66.65; H, 6.04; F, 4.22; N, 12.44; O, 10.65.

Related CAS #:857036-77-2 (maleate)288383-20-0 (free base)

Synonym:AZD2171; AZD 2171; AZD-2171; AZD2171 free base; Cediranib;brand name: Recentin.

IUPAC/Chemical Name:4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

InChi Key:XXJWYDDUDKYVKI-UHFFFAOYSA-N

InChi Code:InChI=1S/C25H27FN4O3/c1-16-12-17-19(29-16)6-7-21(24(17)26)33-25-18-13-22(31-2)23(14-20(18)27-15-28-25)32-11-5-10-30-8-3-4-9-30/h6-7,12-15,29H,3-5,8-11H2,1-2H3

SMILES Code:COC1=CC2=C(OC3=C(F)C4=C(NC(C)=C4)C=C3)N=CN=C2C=C1OCCCN5CCCC5

Technical Data

Additional Information

According to http://en.wikipedia.org/wiki/Cediranib, Cediranib is a potent inhibitor of vascular endothelial growth factor (VEGF) receptor tyrosine kinases. It is being developed by AstraZeneca as a possible anti-cancer chemotherapeutic agent for oral administration. Beginning in 2007, it is undergoing Phase I clinical trials for the treatment of non-small cell lung cancer, kidney cancer, and colorectal cancer in adults, as well as tumors of the central nervous system in children. Phase I trials of interactions with other drugs used in cancer treatment are also underway. On February 27, 2008, AstraZeneca announced that the use of Recentin in non-small cell lung cancer will not progress into phase III after failing to meet its main goal. On 8th March 2010, AstraZeneca issued a press-release stating that Recentin had failed Phase III clinical trials for use in first-line metastatic colorectal cancer when it was compared clinically with the market-leader Avastin.  

References

1: Al-Huniti N, Petersson K, Tang W, Masson E, Li J. Population exposure-safety analysis of cediranib for Phase I and II studies in patients with cancer. Br J Clin Pharmacol. 2017 Dec 22. doi: 10.1111/bcp.13495. [Epub ahead of print] PubMed PMID: 29274100.

2: Andronesi OC, Esmaeili M, Borra RJH, Emblem K, Gerstner ER, Pinho MC, PlotkinSR, Chi AS, Eichler AF, Dietrich J, Ivy SP, Wen PY, Duda DG, Jain R, Rosen BR, Sorensen GA, Batchelor TT. Early changes in glioblastoma metabolism measured by MR spectroscopic imaging during combination of anti-angiogenic cediranib and chemoradiation therapy are associated with survival. NPJ Precis Oncol. 2017;1. pii: 20. doi: 10.1038/s41698-017-0020-3. Epub 2017 Jun 12. PubMed PMID: 29202103; PubMed Central PMCID: PMC5708878.

3: Orbegoso C, Marquina G, George A, Banerjee S. The role of Cediranib in ovarian cancer. Expert Opin Pharmacother. 2017 Oct;18(15):1637-1648. doi: 10.1080/14656566.2017.1383384. PubMed PMID: 28933580.

4: Tsao AS, Moon J, Wistuba II, Vogelzang NJ, Kalemkerian GP, Redman MW, GandaraDR, Kelly K. Phase I Trial of Cediranib in Combination with Cisplatin and Pemetrexed in Chemonaive Patients with Unresectable Malignant Pleural Mesothelioma (SWOG S0905). J Thorac Oncol. 2017 Aug;12(8):1299-1308. doi: 10.1016/j.jtho.2017.05.021. Epub 2017 Jun 6. PubMed PMID: 28599887; PubMed Central PMCID: PMC5690479.

5: Lee JM, Cimino-Mathews A, Peer CJ, Zimmer A, Lipkowitz S, Annunziata CM, Cao L, Harrell MI, Swisher EM, Houston N, Botesteanu DA, Taube JM, Thompson E, Ogurtsova A, Xu H, Nguyen J, Ho TW, Figg WD, Kohn EC. Safety and Clinical Activity of the Programmed Death-Ligand 1 Inhibitor Durvalumab in Combination With Poly (ADP-Ribose) Polymerase Inhibitor Olaparib or Vascular Endothelial Growth Factor Receptor 1-3 Inhibitor Cediranib in Women"s Cancers: A Dose-Escalation, Phase I Study. J Clin Oncol. 2017 Jul 1;35(19):2193-2202. doi: 10.1200/JCO.2016.72.1340. Epub 2017 May 4. PubMed PMID: 28471727; PubMed CentralPMCID: PMC5493052.

6: Jiang W, Liu P, Li X, Wang P. Identification of target genes of cediranib in alveolar soft part sarcoma using a gene microarray. Oncol Lett. 2017 Apr;13(4):2623-2630. doi: 10.3892/ol.2017.5779. Epub 2017 Feb 24. PubMed PMID: 28454442; PubMed Central PMCID: PMC5403492.

7: Stark DP, Cook A, Brown JM, Brundage MD, Embleton AC, Kaplan RS, Raja FA, Swart AMW, Velikova G, Qian W, Ledermann JA. Quality of life with cediranib in relapsed ovarian cancer: The ICON6 phase 3 randomized clinical trial. Cancer. 2017 Jul 15;123(14):2752-2761. doi: 10.1002/cncr.30657. Epub 2017 Mar 24. PubMedPMID: 28339098; PubMed Central PMCID: PMC5516140.

8: Li J, Al-Huniti N, Henningsson A, Tang W, Masson E. Population pharmacokinetic and exposure simulation analysis for cediranib (AZD2171) in pooled Phase I/II studies in patients with cancer. Br J Clin Pharmacol. 2017 Aug;83(8):1723-1733. doi: 10.1111/bcp.13266. Epub 2017 Mar 27. PubMed PMID: 28213941; PubMed Central PMCID: PMC5510068.

9: Melsens E, Verberckmoes B, Rosseel N, Vanhove C, Descamps B, Pattyn P, CeelenW. The VEGFR Inhibitor Cediranib Improves the Efficacy of Fractionated Radiotherapy in a Colorectal Cancer Xenograft Model. Eur Surg Res. 2017;58(3-4):95-108. doi: 10.1159/000452741. Epub 2016 Dec 22. PubMed PMID: 28002822.

10: Tang W, McCormick A, Li J, Masson E. Clinical Pharmacokinetics and Pharmacodynamics of Cediranib. Clin Pharmacokinet. 2017 Jul;56(7):689-702. doi: 10.1007/s40262-016-0488-y. Review. PubMed PMID: 27943222.

11: Bordinhão AL, Evangelista AF, Oliveira RJ, Macedo T, Silveira HC, Reis RM, Marques MM. MicroRNA profiling in human breast cancer cell lines exposed to the anti-neoplastic drug cediranib. Oncol Rep. 2016 Dec;36(6):3197-3206. doi: 10.3892/or.2016.5153. Epub 2016 Oct 7. PubMed PMID: 27748845.

12: Brown N, McBain C, Nash S, Hopkins K, Sanghera P, Saran F, Phillips M, Dungey F, Clifton-Hadley L, Wanek K, Krell D, Jeffries S, Khan I, Smith P, Mulholland P. Multi-Center Randomized Phase II Study Comparing Cediranib plus Gefitinib with Cediranib plus Placebo in Subjects with Recurrent/Progressive Glioblastoma. PLoSOne. 2016 May 27;11(5):e0156369. doi: 10.1371/journal.pone.0156369. eCollection 2016. PubMed PMID: 27232884; PubMed Central PMCID: PMC4883746.

13: Ledermann JA, Embleton AC, Raja F, Perren TJ, Jayson GC, Rustin GJS, Kaye SB, Hirte H, Eisenhauer E, Vaughan M, Friedlander M, González-Martín A, Stark D, Clark E, Farrelly L, Swart AM, Cook A, Kaplan RS, Parmar MKB; ICON6 collaborators. Cediranib in patients with relapsed platinum-sensitive ovarian cancer (ICON6): a randomised, double-blind, placebo-controlled phase 3 trial. Lancet. 2016 Mar 12;387(10023):1066-1074. doi: 10.1016/S0140-6736(15)01167-8. Erratum in: Lancet. 2016 Apr 23;387(10029):1722. PubMed PMID: 27025186.

14: Drazin D, Al-Khouja L, Patel A, Hu J, Phuphanich S. Long-term Remission OverSix Years for a Patient with Recurrent Glioblastoma Treated with Cediranib/Lomustine. Cureus. 2016 Jan 16;8(1):e460. doi: 10.7759/cureus.460. PubMed PMID: 26929887; PubMed Central PMCID: PMC4757029.

15: Ivy SP, Liu JF, Lee JM, Matulonis UA, Kohn EC. Cediranib, a pan-VEGFR inhibitor, and olaparib, a PARP inhibitor, in combination therapy for high gradeserous ovarian cancer. Expert Opin Investig Drugs. 2016;25(5):597-611. doi: 10.1517/13543784.2016.1156857. Epub 2016 Mar 16. Review. PubMed PMID: 26899229.

16: McWhirter E, Quirt I, Gajewski T, Pond G, Wang L, Hui J, Oza A. A phase II study of cediranib, an oral VEGF inhibitor, in previously untreated patients with metastatic or recurrent malignant melanoma. Invest New Drugs. 2016 Apr;34(2):231-5. doi: 10.1007/s10637-016-0324-0. Epub 2016 Feb 3. PubMed PMID: 26841902.

17: Powles T, Brown J, Larkin J, Jones R, Ralph C, Hawkins R, Chowdhury S, Boleti E, Bhal A, Fife K, Webb A, Crabb S, Geldart T, Hill R, Dunlop J, Hall PE, McLaren D, Ackerman C, Beltran L, Nathan P. A randomized, double-blind phase II study evaluating cediranib versus cediranib and saracatinib in patients with relapsed metastatic clear-cell renal cancer (COSAK). Ann Oncol. 2016 May;27(5):880-6. doi: 10.1093/annonc/mdw014. Epub 2016 Jan 22. PubMed PMID: 26802156.

18: Ruscito I, Gasparri ML, Marchetti C, De Medici C, Bracchi C, Palaia I, Imboden S, Mueller MD, Papadia A, Muzii L, Panici PB. Cediranib in ovarian cancer: state of the art and future perspectives. Tumour Biol. 2016 Mar;37(3):2833-9. doi: 10.1007/s13277-015-4781-4. Epub 2016 Jan 11. Review. PubMed PMID: 26753963.

19: Lobo MR, Kukino A, Tran H, Schabel MC, Springer CS Jr, Gillespie GY, Grafe MR, Woltjer RL, Pike MM. Synergistic Antivascular and Antitumor Efficacy with Combined Cediranib and SC6889 in Intracranial Mouse Glioma. PLoS One. 2015 Dec 8;10(12):e0144488. doi: 10.1371/journal.pone.0144488. eCollection 2015. PubMed PMID: 26645398; PubMed Central PMCID: PMC4672903.

20: Tewari KS. Clinical implications for cediranib in advanced cervical cancer. Lancet Oncol. 2015 Nov;16(15):1447-8. doi: 10.1016/S1470-2045(15)00252-1. Epub 2015 Oct 22. PubMed PMID: 26474520.