Cediranib: Difference between revisions
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m Infobox drug: rm/replace deprecated params. Fix unk parameters (via AWB script) |
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| IUPAC_name = 4-[(4-fluoro-2-methyl-1''H''-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline |
| IUPAC_name = 4-[(4-fluoro-2-methyl-1''H''-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline |
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| image = AZD2171.svg |
| image = AZD2171.svg |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| legal_status = |
| legal_status = |
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| routes_of_administration = Oral |
| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| elimination_half-life = 12 to 35 hours |
| elimination_half-life = 12 to 35 hours |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 5664 |
| IUPHAR_ligand = 5664 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 288383-20-0 |
| CAS_number = 288383-20-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = NQU9IPY4K9 |
| UNII = NQU9IPY4K9 |
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| PubChem = 9933475 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 491473 |
| ChEMBL = 491473 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8109103 |
| ChemSpiderID = 8109103 |
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| InChI = 1/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 |
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| InChIKey = XXJWYDDUDKYVKI-UHFFFAOYAE |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = XXJWYDDUDKYVKI-UHFFFAOYSA-N |
| StdInChIKey = XXJWYDDUDKYVKI-UHFFFAOYSA-N |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=25 | H=27 | F=1 | N=4 | O=3 |
| C=25 | H=27 | F=1 | N=4 | O=3 |
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| molecular_weight = 450.505 g/mol |
| molecular_weight = 450.505 g/mol |
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| smiles = Cc4nc5ccc(Oc3ncnc2cc(OCCCN1CCCC1)c(OC)cc23)c(F)c5c4 |
| smiles = Cc4nc5ccc(Oc3ncnc2cc(OCCCN1CCCC1)c(OC)cc23)c(F)c5c4 |
Revision as of 13:38, 27 June 2015
Clinical data | |
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Routes of administration | Oral |
ATC code |
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Pharmacokinetic data | |
Elimination half-life | 12 to 35 hours |
Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
ChemSpider | |
UNII | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.196.628 |
Chemical and physical data | |
Formula | C25H27FN4O3 |
Molar mass | 450.505 g/mol g·mol−1 |
3D model (JSmol) | |
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(what is this?) (verify) |
Cediranib (AZD-2171; tentative trade name Recentin) is a potent inhibitor of vascular endothelial growth factor (VEGF) receptor tyrosine kinases.[1][2][3]
The drug is being developed by AstraZeneca as a possible anti-cancer chemotherapeutic agent for oral administration.
Beginning in 2007, it underwent 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 were also undertaken.
On February 27, 2008, AstraZeneca announced that the use of cediranib in non-small cell lung cancer will not progress into phase III after failing to meet its main goal. On 8 March 2010, AstraZeneca issued a press-release stating that cediranib had failed Phase III clinical trials for use in first-line metastatic colorectal cancer when it was compared clinically with the market-leader bevacizumab.[4] As of November 2012, it was being assessed in double-blind studies for the treatment of methylated Glioblastoma Multiforme at the University of Washington Medical Center at a 20 mg daily dose.
Combination Trials
Findings from a federally funded, NCI-sponsored phase II clinical trial[5] presented at the 50th Annual Meeting of the American Society of Clinical Oncology (May 30 - June 3, 2014, Chicago, Ill; Abstract No: LBA5500),[6] show that the combination of two investigational oral drugs, olaparib (AZD-2281; AstraZeneca), a potential first-in-class poly ADP ribose polymerase or PARP inhibitor and cediranib (AZD-2171; AstraZeneca), an anti-angiogenesis drug, is significantly more active against recurrent, platinum chemotherapy-sensitive disease or ovarian cancer related to mutations in BRCA genes than olaparib alone.[7]
References
- ^ Wedge SR, Kendrew J, Hennequin LF; et al. (May 2005). "AZD2171: a highly potent, orally bioavailable, vascular endothelial growth factor receptor-2 tyrosine kinase inhibitor for the treatment of cancer". Cancer Res. 65 (10): 4389–400. doi:10.1158/0008-5472.CAN-04-4409. PMID 15899831.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ Goss G, Shepherd FA, Laurie S; et al. (December 2008). "A phase I and pharmacokinetic study of daily oral cediranib, an inhibitor of vascular endothelial growth factor tyrosine kinases, in combination with cisplatin and gemcitabine in patients with advanced non-small cell lung cancer: A study of the National Cancer Institute of Canada Clinical Trials Group". Eur. J. Cancer. 45 (5): 782–8. doi:10.1016/j.ejca.2008.10.022. PMID 19091548.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ Nikolinakos P, Heymach JV (June 2008). "The tyrosine kinase inhibitor cediranib for non-small cell lung cancer and other thoracic malignancies". J Thorac Oncol. 3 (6 Suppl 2): S131–4. doi:10.1097/JTO.0b013e318174e910. PMID 18520296.
- ^ "AstraZeneca - RECENTIN did not meet primary endpoint in Horizon III study in metastatic colorectal cancer". Retrieved 17 March 2014.
- ^ "Cediranib Maleate and Olaparib in Treating Patients With Recurrent Ovarian, Fallopian Tube, Peritoneal Cancer, or Triple-Negative Breast Cancer". Retrieved 12 June 2014.
- ^ Liu J, Barry WT, Birrer MJ, et al. A randomized phase 2 trial comparing efficacy of the combination of the PARP inhibitor olaparib and the antiangiogenic cediranib against olaparib alone in recurrent platinum-sensitive ovarian cancer; J Clin Oncol 32:5s, 2014 (suppl; abstr LBA5500))
- ^ Combination of Targeted Drugs May Significantly Increase Progression-Free Survival in Women with Recurrent Ovarian Cancer, Study Shows - Onco'Zine - The International Oncology Network; June 2, 2014