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Details

Stereochemistry ACHIRAL
Molecular Formula C25H27FN4O3
Molecular Weight 450.5062
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEDIRANIB

SMILES

Cc1cc2c(ccc(c2F)Oc3c4cc(c(cc4ncn3)OCCCN5CCCC5)OC)[nH]1

InChI

InChIKey=XXJWYDDUDKYVKI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H27FN4O3
Molecular Weight 450.5062
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Defective differentiation of myeloid and plasmacytoid dendritic cells in advanced cancer patients is not normalized by tyrosine kinase inhibition of the vascular endothelial growth factor receptor.
2007
Gateways to clinical trials.
2007 Dec
Vascular endothelial growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer: a review of recent clinical trials.
2007 May
Gateways to clinical trials.
2008 Apr
Phase I and pharmacokinetic study of daily oral AZD2171, an inhibitor of vascular endothelial growth factor tyrosine kinases, in combination with carboplatin and paclitaxel in patients with advanced non-small-cell lung cancer: the National Cancer Institute of Canada clinical trials group.
2008 Apr 10
Differential response of primary tumor versus lymphatic metastasis to VEGFR-2 and VEGFR-3 kinase inhibitors cediranib and vandetanib.
2008 Aug
Novel anti-angiogenic therapies for malignant gliomas.
2008 Dec
The role of angiogenesis inhibitors in prostate cancer.
2008 Jan-Feb
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
The tyrosine kinase inhibitor cediranib for non-small cell lung cancer and other thoracic malignancies.
2008 Jun
The tyrosine kinase inhibitor cediranib blocks ligand-induced vascular endothelial growth factor receptor-3 activity and lymphangiogenesis.
2008 Jun 15
Inhibition of vascular endothelial growth factor-a signaling induces hypertension: examining the effect of cediranib (recentin; AZD2171) treatment on blood pressure in rat and the use of concomitant antihypertensive therapy.
2008 May 15
Gateways to clinical trials.
2008 Oct
Novel drugs for renal cell carcinoma.
2008 Oct
Therapeutic application of noncytotoxic molecular targeted therapy in gliomas: growth factor receptors and angiogenesis inhibitors.
2008 Sep
Vertical VEGF targeting: A combination of ligand blockade with receptor tyrosine kinase inhibition.
2008 Sep
Systemic therapy after first-line docetaxel in metastatic castration-resistant prostate cancer.
2008 Sep
Speeding up the evaluation of new agents in cancer.
2008 Sep 3
Acoustic radiation force and optical spectroscopy for assessing tumor vessel normalization during anti-angiogenic therapy.
2009
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
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 I study of cediranib in combination with oxaliplatin and infusional 5-Fluorouracil in patients with advanced colorectal cancer.
2009 Feb 15
Phase III trial of FOLFOX plus bevacizumab or cediranib (AZD2171) as first-line treatment of patients with metastatic colorectal cancer: HORIZON III.
2009 Jan
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
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
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
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 (recentin, AZD2171) reverses ABCB1- and ABCC1-mediated multidrug resistance by inhibition of their transport function.
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
Angiogenesis inhibition in prostate cancer: current uses and future promises.
2010
Targeted therapies in epithelial ovarian cancer.
2010
A current review of targeted therapeutics for ovarian cancer.
2010
An open-label, Phase I study of cediranib (RECENTIN) in patients with acute myeloid leukemia.
2010 Feb
CT response assessment combining reduction in both size and arterial phase density correlates with time to progression in metastatic renal cancer patients treated with targeted therapies.
2010 Jan
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
Changes in vascular permeability and expression of different angiogenic factors following anti-angiogenic treatment in rat glioma.
2010 Jan 15
Recent advances and future directions in the management of metastatic renal cell carcinoma.
2010 Mar
Tumor invasion after treatment of glioblastoma with bevacizumab: radiographic and pathologic correlation in humans and mice.
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
Molecularly targeted therapy in hepatocellular carcinoma.
2010 Sep 1
Patents

Sample Use Guides

The recommended dose is 20 mg taken orally, once daily.
Route of Administration: Oral
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 Fri Jun 25 23:49:43 UTC 2021
Edited
by admin
on Fri Jun 25 23:49:43 UTC 2021
Record UNII
NQU9IPY4K9
Record Status Validated (UNII)
Record Version
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Name Type Language
CEDIRANIB
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
CEDIRANIB [USAN]
Common Name English
AZD-2171
Code English
CEDIRANIB [INN]
Common Name English
QUINAZOLINE, 4-((4-FLUORO-2-METHYL-1H-INDOL-5-YL)OXY)-6-METHOXY-7-(3-(1-PYRROLIDINYL)PROPOXY)-
Systematic Name English
4-((4-FLUORO-2-METHYL-1H-INDOL-5-YL)OXY)-6-METHOXY-7-(3-PYRROLIDIN-1-YLPROPOXY)QUINAZOLINE
Systematic Name English
CEDIRANIB [MART.]
Common Name English
CEDIRANIB [WHO-DD]
Common Name English
AZD2171
Code English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
NCI_THESAURUS C1742
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
FDA ORPHAN DRUG 310510
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
WHO-ATC L01XE32
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
EU-Orphan Drug EU/3/14/1303
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
Code System Code Type Description
CAS
288383-20-0
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
INN
8764
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
NCI_THESAURUS
C80867
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
EPA CompTox
288383-20-0
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
FDA UNII
NQU9IPY4K9
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
EVMPD
SUB26524
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
DRUG BANK
DB04849
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL491473
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
WIKIPEDIA
CEDIRANIB
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
PUBCHEM
9933475
Created by admin on Fri Jun 25 23:49:43 UTC 2021 , Edited by admin on Fri Jun 25 23:49:43 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY