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Details

Stereochemistry ACHIRAL
Molecular Formula C27H32ClN5O5
Molecular Weight 542.0275
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARACATINIB

SMILES

CN1CCN(CC1)CCOc2cc3c(c(c2)OC4CCOCC4)c(ncn3)Nc5c(ccc6c5OCO6)Cl

InChI

InChIKey=OUKYUETWWIPKQR-UHFFFAOYSA-N
InChI=1S/C27H32ClN5O5/c1-32-6-8-33(9-7-32)10-13-35-19-14-21-24(23(15-19)38-18-4-11-34-12-5-18)27(30-16-29-21)31-25-20(28)2-3-22-26(25)37-17-36-22/h2-3,14-16,18H,4-13,17H2,1H3,(H,29,30,31)

HIDE SMILES / InChI

Molecular Formula C27H32ClN5O5
Molecular Weight 542.0275
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Saracatinib (AZD0530) is an oral, dual inhibitor of c-Src/Abl kinases initially developed by AstraZeneca for the treatment of cancer. The drug was tested for many neoplasms and reached phase III for ovarian cancer (in combination with paclitaxel), however without demonstrating any significant effect. Sarcatinib is also tested in patients with Alzheimer's Disease (Phase II). Its effect on Alzheimer's Disease patients is explained by inhibition of another kinase, Fyn, which is highly expressed in brain.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cooperative action of tamoxifen and c-Src inhibition in preventing the growth of estrogen receptor-positive human breast cancer cells.
2006 Dec
N-(5-chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5- (tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine, a novel, highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor.
2006 Nov 2
Research provides new hope for tamoxifen-resistant breast cancer patients.
2008 Mar
Src family kinase oncogenic potential and pathways in prostate cancer as revealed by AZD0530.
2008 Oct 23
The Src inhibitor AZD0530 reversibly inhibits the formation and activity of human osteoclasts.
2009 Apr
The Src inhibitor AZD0530 blocks invasion and may act as a radiosensitizer in lung cancer cells.
2009 Apr
A novel Src kinase inhibitor reduces tumour formation in a skin carcinogenesis model.
2009 Feb
The effect of the dual Src/Abl kinase inhibitor AZD0530 on Philadelphia positive leukaemia cell lines.
2009 Feb 13
Aberrant activation of androgen receptor in a new neuropeptide-autocrine model of androgen-insensitive prostate cancer.
2009 Jan 1
Activation of Src and Src-associated signaling pathways in relation to hypoxia in human cancer xenograft models.
2009 Jan 15
Preclinical anticancer activity of the potent, oral Src inhibitor AZD0530.
2009 Jun
Inhibition of Src with AZD0530 reveals the Src-Focal Adhesion kinase complex as a novel therapeutic target in papillary and anaplastic thyroid cancer.
2009 Jun
Antitumor effects and biomarkers of activity of AZD0530, a Src inhibitor, in pancreatic cancer.
2009 Jun 15
A phase II trial of the Src-kinase inhibitor AZD0530 in patients with advanced castration-resistant prostate cancer: a California Cancer Consortium study.
2009 Mar
Quantification of focal adhesion kinase activation loop phosphorylation as a biomarker of Src activity.
2009 Mar
Src inhibitors in early breast cancer: a methodology, feasibility and variability study.
2009 Mar
Combined Src and aromatase inhibition impairs human breast cancer growth in vivo and bypass pathways are activated in AZD0530-resistant tumors.
2009 May 15
Novel dual Src/Abl inhibitors for hematologic and solid malignancies.
2010 Aug
Gene array and fluorescence in situ hybridization biomarkers of activity of saracatinib (AZD0530), a Src inhibitor, in a preclinical model of colorectal cancer.
2010 Aug 15
Effects of the Src inhibitor saracatinib (AZD0530) on renal function in healthy subjects.
2010 Jul
Src family kinase inhibitor Saracatinib (AZD0530) impairs oxaliplatin uptake in colorectal cancer cells and blocks organic cation transporters.
2010 Jul 15
Effect of the specific Src family kinase inhibitor saracatinib on osteolytic lesions using the PC-3 bone model.
2010 Jun
A novel bile acid-activated vitamin D receptor signaling in human hepatocytes.
2010 Jun
Effects of the Src kinase inhibitor saracatinib (AZD0530) on bone turnover in healthy men: a randomized, double-blind, placebo-controlled, multiple-ascending-dose phase I trial.
2010 Mar
Impact of the Src inhibitor saracatinib on the metastatic phenotype of a fibrosarcoma (KHT) tumor model.
2010 Nov
[SRC kinases in tumor therapy].
2010 Oct
Phase I safety, pharmacokinetics, and inhibition of SRC activity study of saracatinib in patients with solid tumors.
2010 Oct 1
Patents

Patents

Sample Use Guides

Alzheimer's Disease: patients receive 100-125 mg daily. Ovarian cancer: patients receive 175 mg once daily in combination with paclitaxel (80 mg/m2 weekly for 6 weeks followed by a 2 week break (1 cycle), for 4 cycles initially (32 weeks)).
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/27766744
Ovarian cancer cell lines (OVCA420, TOV112D, DOV13, A2780, EFO27, SKOV3, PEO1, OV167, Hey, OVCAR8, MCAS, ES2, OVCAR5) were exposed to increasing concentrations of saracatinib (ranging from 0–10 uM).
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:19:59 UTC 2021
Edited
by admin
on Sat Jun 26 06:19:59 UTC 2021
Record UNII
9KD24QGH76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARACATINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
SARACATINIB [USAN]
Common Name English
SARACATINIB [INN]
Common Name English
4-QUINAZOLINAMINE, N-(5-CHLORO-1,3-BENZODIOXOL-4-YL)-7-(2-(4-METHYL-1-PIPERAZINYL)ETHOXY)-5-((TETRAHYDRO-2H-PYRAN-4-YL)OXY)-
Systematic Name English
AZD0530
Code English
AZD-0530
Code English
SARACATINIB [WHO-DD]
Common Name English
N-(5-CHLORO-1,3-BENZODIOXOL-4-YL)-7-(2-(4-METHYLPIPERAZIN-1-YL)ETHOXY)-5-((OXAN-4-YL)OXY)QUINAZOLIN-4-AMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
FDA ORPHAN DRUG 674218
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
NCI_THESAURUS C129825
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C48378
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
DRUG BANK
DB11805
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
CAS
379231-04-6
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
INN
9017
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
EPA CompTox
379231-04-6
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL217092
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
FDA UNII
9KD24QGH76
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
PUBCHEM
10302451
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
MESH
C515233
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
EVMPD
SUB32253
Created by admin on Sat Jun 26 06:19:59 UTC 2021 , Edited by admin on Sat Jun 26 06:19:59 UTC 2021
PRIMARY
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TARGET -> INHIBITOR
INHIBITOR
SALT/SOLVATE -> PARENT
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