Oxyphenisatin acetate

Names

[ CAS No. ]:
115-33-3

[ Name ]:
Oxyphenisatin acetate

[Synonym ]:
3,3-bis-(4-acetoxy-phenyl)-indolin-2-one
Izafenin
3,3-bis[4-(acetyloxy)phenyl]-1,3-dihydro-2H-indol-2-one
Darmoletten
Diphesatine
Acetalax
Contax
Promassolax
3,3-bis(4-acetoxyphenyl)oxindole
Brocatine
Isaphenin
OXYPHENISATIN ACETATE
EINECS 204-083-6
Diphesatin
3,3-Bis-(4-acetoxy-phenyl)-indolin-2-on
oxyphenisatine di(acetate)

Biological Activity

[Description]:

Oxyphenisatin acetate, the pro-drug of oxyphenisatin, is used to be a laxative.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Others

[In Vitro]

Oxyphenisatin acetate inhibits the growth of the breast cancer cell lines MCF7, T47D, HS578T, and MDA-MB-468. In the estrogen receptor (ER) positive MCF7 and T47D cells, oxyphenisatin acetate induces TNFα expression and TNFR1 degradation, indicating autocrine receptor-mediated apoptosis in these lines. Ten micromoles per liter Oxyphenisatin acetate treatment results in autophagy and mitochondrial dysfunction[1].

[In Vivo]

Oxyphenisatin acetate (300 mg/kg, i.p.) delivers intraperitoneally inhibited tumor growth, accompanied by phosphorylation of eIF2α and degradation of TNFR1 in an MCF7 xenograft model[1].

[Animal admin]

Assessment in several other tumor models demonstrates tolerability with oxyphenisatin acetate at 300 mg/kg given once daily or 200 mg/kg given twice daily. For the MCF-7 study treatments are administered on an exact body weight basis using dose volumes of 1-2 mL/kg body weight. The vehicle control receives 100% DMSO. The treated group receives 300 mg/kg oxyphenisatin acetate once daily for a total of 10 days, followed by a 3 day rest and an additional 6 days of dosing. The dose solutions are prepared in 100% DMSO, aliquoted and stored frozen until used. The mice are monitored for a total of 52 days with treatment initiation occurring on day 27 posttumor implantation[1].

[References]

[1]. Morrison BL, et al. Oxyphenisatin acetate (NSC 59687) triggers a cell starvation response leading to autophagy, mitochondrial dysfunction, and autocrine TNFα-mediated apoptosis. Cancer Med. 2013 Oct;2(5):687-700.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.282 g/cm3

[ Boiling Point ]:
566.5ºC at 760 mmHg

[ Melting Point ]:
244℃

[ Molecular Formula ]:
C₂₄H₁₉NO₅

[ Molecular Weight ]:
401.41100

[ Flash Point ]:
296.4ºC

[ Exact Mass ]:
401.12600

[ PSA ]:
81.70000

[ LogP ]:
3.96170

[ Vapour Pressure ]:
7.5E-13mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
2-8℃

Safety Information

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%