U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

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

SHOW SMILES / InChI
Structure of CEDIRANIB

SMILES

COC1=C(OCCCN2CCCC2)C=C3N=CN=C(OC4=C(F)C5=C(NC(C)=C5)C=C4)C3=C1

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 450.5053
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
A pilot study to evaluate the vascular endothelial growth factor receptor tyrosine kinase inhibitor AZD2171 and chemotherapy in locally advanced and inflammatory breast cancer.
2005 Dec
A physiologic imaging pilot study of breast cancer treated with AZD2171.
2006 Jan 1
Anti-angiogenic and anti-HER therapy.
2006 Jul
Gateways to clinical trials.
2007 Apr
Acute pharmacodynamic and antivascular effects of the vascular endothelial growth factor signaling inhibitor AZD2171 in Calu-6 human lung tumor xenografts.
2007 Aug
Gateways to clinical trials.
2007 Dec
Dual inhibition of EGFR and VEGFR pathways in combination with irradiation: antitumour supra-additive effects on human head and neck cancer xenografts.
2007 Jul 2
Phase I clinical study of AZD2171, an oral vascular endothelial growth factor signaling inhibitor, in patients with advanced solid tumors.
2007 Jul 20
Vascular endothelial growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer: a review of recent clinical trials.
2007 May
AZD2171 shows potent antitumor activity against gastric cancer over-expressing fibroblast growth factor receptor 2/keratinocyte growth factor receptor.
2007 May 15
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
Anti-angiogenic targets in the treatment of advanced renal cell carcinoma.
2008 Dec
Development of sorafenib and other molecularly targeted agents in hepatocellular carcinoma.
2008 Jan 15
The role of angiogenesis inhibitors in prostate cancer.
2008 Jan-Feb
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
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
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
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
Concerns about anti-angiogenic treatment in patients with glioblastoma multiforme.
2009 Dec 16
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
Antiangiogenic drugs in ovarian cancer.
2009 Jan 13
Treatment in advanced colorectal cancer: what, when and how?
2009 Jun 2
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
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
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
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
Angiogenesis inhibition in prostate cancer: current uses and future promises.
2010
An open-label, Phase I study of cediranib (RECENTIN) in patients with acute myeloid leukemia.
2010 Feb
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
CD133+ circulating haematopoietic progenitor cells predict for response to sorafenib plus erlotinib in non-small cell lung cancer patients.
2010 Jan 19
Sorafenib in patients with advanced biliary tract carcinoma: a phase II trial.
2010 Jan 5
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
Rapid development of hypertension and proteinuria with cediranib, an oral vascular endothelial growth factor receptor inhibitor.
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
Sunitinib in combination with docetaxel in patients with advanced solid tumors: a phase I dose-escalation study.
2010 Sep
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 Dec 15 16:26:47 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:47 GMT 2023
Record UNII
NQU9IPY4K9
Record Status Validated (UNII)
Record Version
  • Download
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
Cediranib [WHO-DD]
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
AZD2171
Code English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
FDA ORPHAN DRUG 310510
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
WHO-ATC L01XE32
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
EU-Orphan Drug EU/3/14/1303
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
Code System Code Type Description
CAS
288383-20-0
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
INN
8764
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
USAN
TT-141
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
NCI_THESAURUS
C80867
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID10183035
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
FDA UNII
NQU9IPY4K9
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
EVMPD
SUB26524
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
SMS_ID
100000090090
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
DRUG BANK
DB04849
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL491473
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
WIKIPEDIA
CEDIRANIB
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
PUBCHEM
9933475
Created by admin on Fri Dec 15 16:26:48 GMT 2023 , Edited by admin on Fri Dec 15 16:26:48 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY