Saracatinib Chemical Properties

Melting point:

84-89°C

Boiling point:

671.2±55.0 °C(Predicted)

Density 

1.348

storage temp. 

-20°C

solubility 

Soluble in DMSO (50 mg/ml) and ethanol (54 mg/mL with warming)

pka

7.55±0.10(Predicted)

form 

solid

color 

White

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

InChIKey

OUKYUETWWIPKQR-UHFFFAOYSA-N

SMILES

N1=C2C(C(OC3CCOCC3)=CC(OCCN3CCN(C)CC3)=C2)=C(NC2=C3C(=CC=C2Cl)OCO3)N=C1

Saracatinib Usage And Synthesis

Description

Saracatinib is a dual inhibitor of the tyrosine kinases c-Src and Abl (IC₅₀ = 2.7 and 30 nM, respectively). It less effectively inhibits other receptor and non-receptor tyrosine kinases as well as assorted serine/threonine kinases. Saracatinib is orally available and blocks cell motility, migration, adhesion, invasion, proliferation, differentiation, and survival. Through its effects on c-Src, it reduces osteoclast bone resorption. Saracatinib also blocks denque virus RNA replication through its effect on Fyn kinase.

Chemical Properties

White Solid

Uses

An oral, selective dual inhibitor of Src and ABL kinase. It is a COVID19-related research product.

Definition

ChEBI: Saracatinib is a member of the class of quinazolines that is quinazoline substituted by (5-chloro-2H-1,3-benzodioxol-4-yl)amino, (oxan-4-yl)oxy and 2-(4-methylpiperazin-1-yl)ethoxy groups at positions 4, 5 and 7, respectively. It is a dual inhibitor of the tyrosine kinases c-Src and Abl (IC50 = 2.7 and 30 nM, respectively). Saracatinib was originally developed by AstraZeneca for the treatment of cancer but in 2019 it was granted orphan drug designation by the US Food and Drug Administration for the treatment of idiopathic pulmonary fibrosis (IPF), a type of lung disease that results in scarring (fibrosis) of the lungs. It has a role as an antineoplastic agent, an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, a radiosensitizing agent, an autophagy inducer, an apoptosis inducer and an anticoronaviral agent. It is a member of quinazolines, a secondary amino compound, a N-methylpiperazine, an aromatic ether, a member of oxanes, a member of benzodioxoles, an organochlorine compound and a diether.

storage

Store at -20°C

References

[1] LAURENT F. HENNEQUIN. 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†[J]. Journal of Medicinal Chemistry, 2006, 49 22: 6465-6488. DOI:10.1021/jm060434q
[2] TIM P. GREEN . Preclinical anticancer activity of the potent, oral Src inhibitor AZD0530[J]. Molecular Oncology, 2009, 3 3: Pages 248-261. DOI:10.1016/j.molonc.2009.01.002
[3] MELISSANNE DE WISPELAERE  Priscilla L Y  Amy J LaCroix. The small molecules AZD0530 and dasatinib inhibit dengue virus RNA replication via Fyn kinase.[J]. Journal of Virology, 2013: 7367-7381. DOI:10.1128/jvi.00632-13
[4] JIN SOO SHIN. Saracatinib Inhibits Middle East Respiratory Syndrome-Coronavirus Replication In Vitro.[J]. Viruses, 2018. DOI:10.3390/v10060283
[5] SI JIE TANG. Fyn kinase inhibition reduces protein aggregation, increases synapse density and improves memory in transgenic and traumatic Tauopathy.[J]. Acta Neuropathologica Communications, 2020: 96. DOI:10.1186/s40478-020-00976-9
[6] ADAM C. KAUFMAN BS, PHD  Stephen M S M, PHD. Fyn inhibition rescues established memory and synapse loss in Alzheimer mice[J]. Annals of Neurology, 2015, 77 6: 953-971. DOI:10.1002/ana.24394

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