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Details

Stereochemistry ACHIRAL
Molecular Formula C25H27FN4O3.C4H4O4
Molecular Weight 566.5774
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEDIRANIB MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC2=C(C=C1OCCCN3CCCC3)N=CN=C2OC4=CC=C5NC(C)=CC5=C4F

InChI

InChIKey=JRMGHBVACUJCRP-BTJKTKAUSA-N
InChI=1S/C25H27FN4O3.C4H4O4/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;5-3(6)1-2-4(7)8/h6-7,12-15,29H,3-5,8-11H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C25H27FN4O3
Molecular Weight 450.5053
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Cediranib (AZD-2171) is a VEGFR-2 kinase inhibitor which was developed by AstraZeneca for the treatment of cancer. The drug reached the final stage of approval by European Medicines Agency in 2008 under the name Zemfirza (it was recommended to be taken in combination with platinum-based chemotherapy), however on 19 September 2016 AstraZeneca decided to withdraw the Marketing Authorisation Application.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Anti-angiogenic targets in the treatment of advanced renal cell carcinoma.
2008 Dec
Novel anti-angiogenic therapies for malignant gliomas.
2008 Dec
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Gateways to clinical trials.
2008 Oct
Targeting angiogenesis in the treatment of lung cancer.
2008 Oct
Inhibition of vascular endothelial growth factor signalling using cediranib (RECENTIN; AZD2171) enhances radiation response and causes substantial physiological changes in lung tumour xenografts.
2008 Oct
Novel drugs for renal cell carcinoma.
2008 Oct
[Tumor vasculature as a therapeutic target in non-small cell lung cancer].
2008 Sep
Therapeutic application of noncytotoxic molecular targeted therapy in gliomas: growth factor receptors and angiogenesis inhibitors.
2008 Sep
Speeding up the evaluation of new agents in cancer.
2008 Sep 3
Current available therapies and future directions in the treatment of malignant gliomas.
2009
PDGF-C induces maturation of blood vessels in a model of glioblastoma and attenuates the response to anti-VEGF treatment.
2009
Noninvasive imaging of the functional effects of anti-VEGF therapy on tumor cell extravasation and regional blood volume in an experimental brain metastasis model.
2009
VEGF inhibitors in the treatment of cerebral edema in patients with brain cancer.
2009 Apr
An exploratory survival analysis of anti-angiogenic therapy for recurrent malignant glioma.
2009 Apr
Examining the acute effects of cediranib (RECENTIN, AZD2171) treatment in tumor models: a dynamic contrast-enhanced MRI study using gadopentate.
2009 Apr
Antitumor and antiangiogenic activity of cediranib in a preclinical model of renal cell carcinoma.
2009 Dec
Increase in tumour permeability following TGF-beta type I receptor-inhibitor treatment observed by dynamic contrast-enhanced MRI.
2009 Dec 1
Effective strategies for management of hypertension after vascular endothelial growth factor signaling inhibition therapy: results from a phase II randomized, factorial, double-blind study of Cediranib in patients with advanced solid tumors.
2009 Dec 20
Phase III trial of FOLFOX plus bevacizumab or cediranib (AZD2171) as first-line treatment of patients with metastatic colorectal cancer: HORIZON III.
2009 Jan
Antiangiogenic drugs in ovarian cancer.
2009 Jan 13
Investigational agents in the management of non-small cell lung cancer.
2009 Jul
A "vascular normalization index" as potential mechanistic biomarker to predict survival after a single dose of cediranib in recurrent glioblastoma patients.
2009 Jul 1
VEGF inhibitors and prostate cancer therapy.
2009 Jun
Treatment in advanced colorectal cancer: what, when and how?
2009 Jun 2
Gateways to clinical trials.
2009 Mar
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.
2009 Mar
The vascular endothelial growth factor receptor-2 tyrosine kinase inhibitor cediranib (Recentin; AZD2171) inhibits endothelial cell function and growth of human renal tumor xenografts.
2009 Mar 1
[Second-line treatment using novel chemotherapeutic and biologic agents].
2009 May
Current status of cediranib: the rapid development of a novel anti-angiogenic therapy.
2009 May
Edema control by cediranib, a vascular endothelial growth factor receptor-targeted kinase inhibitor, prolongs survival despite persistent brain tumor growth in mice.
2009 May 20
Gateways to clinical trials.
2009 Nov
Phase I, dose escalation and pharmacokinetic study of cediranib (RECENTIN), a highly potent and selective VEGFR signaling inhibitor, in Japanese patients with advanced solid tumors.
2009 Nov
Cediranib, an oral inhibitor of vascular endothelial growth factor receptor kinases, is an active drug in recurrent epithelial ovarian, fallopian tube, and peritoneal cancer.
2009 Nov 20
Cediranib: profile of a novel anti-angiogenic agent in patients with glioblastoma.
2009 Oct
Targeting vascular endothelial growth factor receptor-1 and -3 with cediranib (AZD2171): effects on migration and invasion of gastrointestinal cancer cell lines.
2009 Sep
VEGFR1 activity modulates myeloid cell infiltration in growing lung metastases but is not required for spontaneous metastasis formation.
2009 Sep 18
DCE-MRI assessment of the effect of vandetanib on tumor vasculature in patients with advanced colorectal cancer and liver metastases: a randomized phase I study.
2009 Sep 21
Targeted therapy in ovarian cancer.
2010
Targeted therapies in epithelial ovarian cancer.
2010
An open-label, Phase I study of cediranib (RECENTIN) in patients with acute myeloid leukemia.
2010 Feb
Treatment options for small cell lung cancer - do we have more choice?
2010 Feb 16
Randomized, double-blind trial of carboplatin and paclitaxel with either daily oral cediranib or placebo in advanced non-small-cell lung cancer: NCIC clinical trials group BR24 study.
2010 Jan 1
Sorafenib in patients with advanced biliary tract carcinoma: a phase II trial.
2010 Jan 5
Tumor invasion after treatment of glioblastoma with bevacizumab: radiographic and pathologic correlation in humans and mice.
2010 Mar
Tyrosine kinase inhibitors to treat liver cancer.
2010 Mar
Phase I evaluation of cediranib, a selective VEGFR signalling inhibitor, in combination with gefitinib in patients with advanced tumours.
2010 Mar
Anti-angiogenic tyrosine kinase inhibitors: what is their mechanism of action?
2010 Mar
Initial assessment, surveillance, and management of blood pressure in patients receiving vascular endothelial growth factor signaling pathway inhibitors.
2010 May 5
Molecularly targeted therapy in hepatocellular carcinoma.
2010 Sep 1
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose is 20 mg taken orally, once daily.
Route of Administration: Oral
In Vitro Use Guide
NCI-H526 cells were treated with Cediranib for 72 hours (0.001 nM, 0.01 nM, 0.1 nM, 1 nM, 10 nM, 100 nM). Cediranib inhibited SCF-stimulated proliferation of cells with an IC50 value of 0.013 nmol/L.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:01:11 UTC 2019
Edited
by admin
on Tue Oct 22 00:01:11 UTC 2019
Record UNII
68AYS9A614
Record Status Validated (UNII)
Record Version
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Name Type Language
CEDIRANIB MALEATE
JAN   MART.   USAN  
USAN  
Official Name English
AZD2171 MALEATE
Code English
CEDIRANIB MALEAT
WHO-DD  
Common Name English
RECENTIN
Brand Name English
QUINAZOLINE, 4-((4-FLUORO-2-METHYL-1H-INDOL-5-YL)OXY)-6-METHOXY-7-(3-(1-PYRROLIDINYL)PROPOXY)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
CEDIRANIB MALEATE [JAN]
Common Name English
AZD-2171 MALEATE
Code English
CEDIRANIB MALEATE [USAN]
Common Name English
CEDIRANIB MALEATE [MART.]
Common Name English
CEDIRANIB MALEAT [WHO-DD]
Common Name English
4-((4-FLUORO-2-METHYL-1H-INDOL-5-YL)OXY)-6-METHOXY-7-(3-PYRROLIDIN-1-YLPROPOXY)QUINAZOLINE (2Z)-BUT-2-ENEDIOATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
NCI_THESAURUS C1742
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
Code System Code Type Description
EVMPD
SUB176736
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
PRIMARY
ChEMBL
CHEMBL491473
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
PRIMARY
NCI_THESAURUS
C48379
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
PRIMARY
CAS
857036-77-2
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
PRIMARY
PUBCHEM
11226834
Created by admin on Tue Oct 22 00:01:11 UTC 2019 , Edited by admin on Tue Oct 22 00:01:11 UTC 2019
PRIMARY
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