Basic information Safety Supplier Related

5-Aziridino-2,4-dinitrobenzamide

Basic information Safety Supplier Related

5-Aziridino-2,4-dinitrobenzamide Basic information

Product Name:
5-Aziridino-2,4-dinitrobenzamide
Synonyms:
  • CB 1954;CB-1954
  • 5-(1-aziridinyl)-2,4-dinitrobenzamide
  • NSC 115829
  • tretazicar
  • 5-(1-Aziridinyl)-2,4-dinitrobenzamide, 5-(Aziridin-1-yl)-2,4-dinitrobenzamide
  • 5-Aziridino-2,4-dinitrobenzamide
  • 2,4-Dinitro-5-(aziridine-1-yl)benzamide
  • CB-954
CAS:
21919-05-1
MF:
C9H8N4O5
MW:
252.18
Mol File:
21919-05-1.mol
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5-Aziridino-2,4-dinitrobenzamide Chemical Properties

Melting point:
173 °C
Boiling point:
427.2±45.0 °C(Predicted)
Density 
1.671±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Acetonitrile (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
solid
pka
14.23±0.50(Predicted)
color 
Yellow to Dark Yellow
InChIKey
WOCXQMCIOTUMJV-UHFFFAOYSA-N
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Safety Information

WGK Germany 
3
HS Code 
2933.99.7500
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5-Aziridino-2,4-dinitrobenzamide Usage And Synthesis

Description

CB-1954 is a prodrug that is enzymatically activated to generate an antitumor agent that forms DNA-DNA interstrand crosslinks. In rat Walker 256 carcinoma cells, CB-1954 is reduced by NAD(P)H:quinone oxidoreductase (NQO1) to the cytotoxic derivative 5-(aziridin-1-yl)-4-hydroxylamineo 2 nitrobenzamide, a bifunctional alkylating agent.

Uses

5-Aziridino-2,4-dinitrobenzamide is an anticancer prodrug used in gene therapy research and is known to be activated by NAD(P)H Quinone Oxidoreductase 2.

Uses

Tretazicar is an anticancer prodrug used in gene therapy research and is known to be activated by NAD(P)H Quinone Oxidoreductase 2.

Biochem/physiol Actions

CB 1954 is an anticancer prodrug used in gene therapy research; activated by NAD(P)H quinone oxidoreductase?2.

in vivo

Tretazicar (CB 1954) (80 mg/kg; i.p. on days 2 and 9) results in a significant increase in survival[3].

Animal Model:Female BALB/c mice (AB22-nr, SKOV3 human ovarian tumour xenograft)[3]
Dosage:80 mg/kg
Administration:i.p. on days 2 and 9
Result:The median survival of the AB22-nr was 49 days. Resulted in a significant increase in survival.

References

[1] R J KNOX. Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy.[J]. Cancer research, 2000, 60 15: 4179-4186.

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