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Apaziquone

Names

[ CAS No. ]:
114560-48-4

[ Name ]:
Apaziquone

[Synonym ]:
Neoquin
NOR-701
1H-Indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propen-1-yl)-1-methyl-
EO-9
5-(1-Aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propen-1-yl)-1-methyl-1H-indole-4,7-dione
Apaziquonum
Apaziquone
EOquin

Biological Activity

[Description]:

Apaziquone (EO-9), an analog of Mitomycin C, is a prodrug that is activated to DNA damaging species by oxidoreductases (particularly NQO1). Apaziquone has the ability to kill aerobic and/or hypoxic cancer cells. Apaziquone, a bioreductive alkylating agent, inhibits cell proliferation and induces apoptosis in oral squamous cell carcinoma (OSCC) cells. Apaziquone significantly reduces oral tumor xenograft volume in immunocompromised NOD/SCID/Crl mice[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[References]

[1]. Gunjan Srivastava, et al. Anticancer Activity of Apaziquone in Oral Cancer Cells and Xenograft Model: Implications for Oral Cancer Therapy. PLoS One. 2015 Jul 24;10(7):e0133735.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
632.3±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H16N2O4

[ Molecular Weight ]:
288.298

[ Flash Point ]:
336.2±31.5 °C

[ Exact Mass ]:
288.110992

[ PSA ]:
82.54000

[ LogP ]:
-1.36

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.682

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NL7873970
CHEMICAL NAME :
1H-Indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-pro penyl)-1-methyl-, (E)-
CAS REGISTRY NUMBER :
114560-48-4
LAST UPDATED :
199709
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C15-H16-N2-O4
MOLECULAR WEIGHT :
288.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>450 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EJCTEA European Journal of Cancer Part A. (Pergamon Press, c/o Elsevier Science, 660 White Plains Rd., Tarrytown, NY 10591) V.28A(4/5)- 1992- Volume(issue)/page/year: 29A,897,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
13 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EJCTEA European Journal of Cancer Part A. (Pergamon Press, c/o Elsevier Science, 660 White Plains Rd., Tarrytown, NY 10591) V.28A(4/5)- 1992- Volume(issue)/page/year: 29A,897,1993

Synthetic Route

Click to get detail synthetic route

Related Compounds

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