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Details

Stereochemistry ACHIRAL
Molecular Formula C25H27FN4O3.C4H4O4
Molecular Weight 566.5774
Optical Activity NONE
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=C(OCCCN2CCCC2)C=C3N=CN=C(OC4=C(F)C5=C(NC(C)=C5)C=C4)C3=C1

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 C25H27FN4O3
Molecular Weight 450.5053
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2006 Dec
A physiologic imaging pilot study of breast cancer treated with AZD2171.
2006 Jan 1
Inhibiting vascular endothelial growth factor receptor-2 signaling reduces tumor burden in the ApcMin/+ mouse model of early intestinal cancer.
2006 Oct
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 Apr
Acute pharmacodynamic and antivascular effects of the vascular endothelial growth factor signaling inhibitor AZD2171 in Calu-6 human lung tumor xenografts.
2007 Aug
Vascular endothelial growth factor receptor tyrosine kinase inhibitors vandetanib (ZD6474) and AZD2171 in lung cancer.
2007 Aug 1
The tyrosine kinase inhibitor, AZD2171, inhibits vascular endothelial growth factor receptor signaling and growth of anaplastic thyroid cancer in an orthotopic nude mouse model.
2007 Aug 1
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
AZD2171 shows potent antitumor activity against gastric cancer over-expressing fibroblast growth factor receptor 2/keratinocyte growth factor receptor.
2007 May 15
Gateways to clinical trials.
2008 Apr
Novel anti-angiogenic therapies for malignant gliomas.
2008 Dec
Gateways to clinical trials.
2008 Oct
Therapeutic application of noncytotoxic molecular targeted therapy in gliomas: growth factor receptors and angiogenesis inhibitors.
2008 Sep
PDGF-C induces maturation of blood vessels in a model of glioblastoma and attenuates the response to anti-VEGF treatment.
2009
Treatment in advanced colorectal cancer: what, when and how?
2009 Jun 2
Current status of cediranib: the rapid development of a novel anti-angiogenic therapy.
2009 May
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
Antivascular therapy for epithelial ovarian cancer.
2010
Changes in vascular permeability and expression of different angiogenic factors following anti-angiogenic treatment in rat glioma.
2010 Jan 15
Tyrosine kinase inhibitors to treat liver cancer.
2010 Mar
Sunitinib in combination with docetaxel in patients with advanced solid tumors: a phase I dose-escalation study.
2010 Sep
Patents

Patents

07074800
5
07851623
2
08492560
6
20030144298
5
JP2011088936A
2
JP2011512395A
4

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 Fri Dec 15 15:55:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:43 GMT 2023
Record UNII
68AYS9A614
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
Code System Code Type Description
EVMPD
SUB176736
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL491473
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
DRUG BANK
DBSALT002394
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
NSC
732208
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
NCI_THESAURUS
C48379
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
CAS
857036-77-2
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
PUBCHEM
11226834
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
SMS_ID
100000162765
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
USAN
TT-142
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
FDA UNII
68AYS9A614
Created by admin on Fri Dec 15 15:55:43 GMT 2023 , Edited by admin on Fri Dec 15 15:55:43 GMT 2023
PRIMARY
Related Record Type Details
Structure of MALEIC ACID
PARENT -> SALT/SOLVATE
Structure of CEDIRANIB
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CEDIRANIB
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