Apaziquone

Modify Date: 2024-01-07 17:45:34

Apaziquone Structure
Apaziquone structure
Common Name Apaziquone
CAS Number 114560-48-4 Molecular Weight 288.298
Density 1.5±0.1 g/cm3 Boiling Point 632.3±55.0 °C at 760 mmHg
Molecular Formula C15H16N2O4 Melting Point N/A
MSDS N/A Flash Point 336.2±31.5 °C

 Use of Apaziquone


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].

 Names

Name 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione
Synonym More Synonyms

 Apaziquone 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
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

~%

Apaziquone Structure

Apaziquone

CAS#:114560-48-4

Literature: Synthesis, , # 5 p. 633 - 636

 Synonyms

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
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