Oxyphenisatine

Names

[ CAS No. ]:
125-13-3

[ Name ]:
Oxyphenisatine

[Synonym ]:
Phenolisatin
Oxyphenisatine
Propellax
Hoscolax
Neodrast
3,3-bis-(4-hydroxy-phenyl)-indolin-2-one
EINECS 204-728-1
Veripaque
3,3-bis(4'-hydroxyphenyl)-2-oxo-2,3-dihydroindole
Diphenolisatin
3,3-bis-(4-hydroxy-phenyl)-1,3-dihydro-indol-2-one
Normalax
Oxyphenisatin
Isatinbisphenol
3,3-bis-(4-hydroxyphenyl)-2-indolinone

Biological Activity

[Description]:

Oxyphenisatine (Oxyphenisatin) is a laxative. Oxyphenisatin acetate is the pro-drug of oxyphenisatin with anticancer activity.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[In Vitro]

Oxyphenisatin has been shown to have antiproliferative activity. Oxyphenisatin acetate (OXY, NSC 59687) is the pro-drug of oxyphenisatin. OXY inhibits the growth of the breast cancer cell lines MCF7, T47D, HS578T, and MDA-MB-468 (IC50=0.8, 0.6, 2.1, 1.8 μM). This effect is associated with selective inhibition of translation accompanied by rapid phosphorylation of the nutrient sensing eIF2α kinases, GCN2 and PERK[1].

[In Vivo]

Toxicity studies demonstrate that mice tolerate IP administration of OXY at 300 mg/kg once daily or 200 mg/kg twice daily. Administration of OXY at 300 mg/kg IP once daily for 10 days results in significantly smaller tumors from day 33 to day 52[1].

[Animal admin]

Mice: When tumors reaches 120 mg, mice are randomized into treatment groups and therapy is initiated. Asimple toxicity assessment to determine tolerability to OXY is conducted by administering single intraperitoneal (IP) doses of compound at 100, 200, and 400 mg/kg. The mice were observed for adverse effects for 14 days postdose[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]:
1.352g/cm3

[ Boiling Point ]:
562.9ºC at 760 mmHg

[ Molecular Formula ]:
C₂₀H₁₅NO₃

[ Molecular Weight ]:
317.33800

[ Flash Point ]:
294.2ºC

[ Exact Mass ]:
317.10500

[ PSA ]:
69.56000

[ LogP ]:
3.52230

[ Vapour Pressure ]:
2.82E-13mmHg at 25°C

[ Index of Refraction ]:
1.691

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM2083780

CHEMICAL NAME :: 2-Indolinone, 3,3-bis(p-hydroxyphenyl)-

CAS REGISTRY NUMBER :: 125-13-3

BEILSTEIN REFERENCE NO. :: 0286070

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H15-N-O3

MOLECULAR WEIGHT :: 317.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 300 ug/kg/36H-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Liver - jaundice, other or unclassified Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 285,813,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 214 ug/kg/1D

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Liver - jaundice, other or unclassified Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 285,813,1971

Safety Information

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933790090

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