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Details

Stereochemistry ACHIRAL
Molecular Formula C22H19ClN4O5.ClH.H2O
Molecular Weight 509.339
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIVOZANIB HYDROCHLORIDE

SMILES

O.Cl.COC1=CC2=C(C=C1OC)C(OC3=CC(Cl)=C(NC(=O)NC4=NOC(C)=C4)C=C3)=CC=N2

InChI

InChIKey=RQXMKRRBJITKRN-UHFFFAOYSA-N
InChI=1S/C22H19ClN4O5.ClH.H2O/c1-12-8-21(27-32-12)26-22(28)25-16-5-4-13(9-15(16)23)31-18-6-7-24-17-11-20(30-3)19(29-2)10-14(17)18;;/h4-11H,1-3H3,(H2,25,26,27,28);1H;1H2

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23788831

Tivozanib (formerly AV-951, KRN-951) is a potent and selective VEGFR tyrosine kinase inhibitor and inhibits angiogenesis and vascular permeability in tumor tissues. It completed phase III a trial investigation for the treatment of renal cell carcinomas, but has not been still approved. In addition, this drug is in the phase II of clinical trial for the investigation it in patients with glioblastoma and colorectal carcinoma.

Originator

Approval Year

2021
470
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
KRN951, a highly potent inhibitor of vascular endothelial growth factor receptor tyrosine kinases, has antitumor activities and affects functional vascular properties.
2006 Sep 15
Anti-tumor activity and tumor vessel normalization by the vascular endothelial growth factor receptor tyrosine kinase inhibitor KRN951 in a rat peritoneal disseminated tumor model.
2008 Mar
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
2011 Oct 30
Vascular endothelial growth factor (VEGF) receptors: drugs and new inhibitors.
2012 Dec 27
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
2013 Apr 15
Patents

Patents

07166722
3
07211587
5

Sample Use Guides

In Vivo Use Guide
Advanced Renal Cell Carcinoma: 1.5 mg orally once daily. Subjects will receive 1.5 mg tivozanib once daily beginning on Day 1 for 3 weeks followed by 1 week off treatment. One cycle will be defined as 4 weeks of treatment. Cycles will be repeated every 4 weeks.
Route of Administration: Oral
In Vitro Use Guide
KRN951 (TIVOZANIB) potently inhibited VEGF-induced VEGFR-2 phosphorylation in endothelial cells at in vitro subnanomolar IC50 values (IC50 = 0.16 nmol/L). It also inhibited ligand-induced phosphorylation of platelet-derived growth factor receptor-beta (PDGFR-beta) and c-Kit (IC50 = 1.72 and 1.63 nmol/L, respectively). KRN951 blocked VEGF-dependent, but not VEGF-independent, activation of mitogen-activated protein kinases and proliferation of endothelial cells. In addition, it inhibited VEGF-mediated migration of human umbilical vein endothelial cells.
Name Type Language
TIVOZANIB HYDROCHLORIDE
DASH   USAN   WHO-DD  
USAN  
Official Name English
UREA, N-(2-CHLORO-4-((6,7-DIMETHOXY-4-QUINOLINYL)OXY)PHENYL)-N'- (5-METHYL-3-ISOXAZOLYL)-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
TIVOZANIB HYDROCHLORIDE [ORANGE BOOK]
Common Name English
(TIVOZANIB HYDROCHLORIDE HYDRATE
Common Name English
TIVOZANIB HYDROCHLORIDE [USAN]
Common Name English
FOTIVDA
Brand Name English
Tivozanib hydrochloride [WHO-DD]
Common Name English
Tivozanib hydrochloride monohydrate [WHO-DD]
Common Name English
TIVOZANIB HYDROCHLORIDE MONOHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C93259
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
Code System Code Type Description
CAS
682745-41-1
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL1289494
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
PUBCHEM
11547978
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
RXCUI
2534245
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
EU-Orphan Drug
EU/3/10/747 (POSITIVE)
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY Treatment of renal-cell carcinoma 9/6/2010 Positive
EVMPD
SUB181449
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
NCI_THESAURUS
C152666
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
SMS_ID
100000167094
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
DAILYMED
8A9H4VK35Z
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
FDA UNII
8A9H4VK35Z
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
USAN
ZZ-29b
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
DRUG BANK
DBSALT002078
Created by admin on Sat Dec 16 01:30:52 GMT 2023 , Edited by admin on Sat Dec 16 01:30:52 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of TIVOZANIB
NIH
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