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Substance Name: Apaziquone [USAN:INN]
RN: 114560-48-4
UNII: H464ZO600O
InChIKey: MXPOCMVWFLDDLZ-NSCUHMNNSA-N

Note

  • NCI: An indolequinone bioreductive prodrug and analog of mitomycin C with potential antineoplastic and radiosensitization activities. Apaziquone is converted to active metabolites in hypoxic cells by intracellular reductases, which are present in greater amounts in hypoxic tumor cells. The active metabolites alkylate DNA, resulting in apoptotic cell death. This agent displays activity towards both hypoxic solid tumors, which exhibits higher expression of cytochrome P450 reductase, and well-oxygenated malignant cells that overexpress the bioreductive enzyme NQO1 (NAD(P)H: quinone oxidoreductase). Apaziquone may selectively sensitize hypoxic tumor cells to radiocytotoxicity. (NCI Thesaurus)

Molecular Formula

  • C15-H16-N2-O4

Molecular Weight

  • 288.3014
 

Classification Codes

  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Apaziquone
  • Apaziquone [USAN:INN]

Synonyms

  • (E)-5-(1-Azirinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione
  • 5-(Azridin-1-yl)-3-(hydroxymethyl)-2-((1E)-3-hydroxyprop-1-enyl)-methyl-1H-indole-4,7-dione
  • Apaziquone
  • Apaziquonum
  • Apaziquonum [INN-Latin]
  • E 09
  • E-85/053
  • EO 9 (pharmaceutical)
  • EO9
  • EOquin
  • NOR-701
  • NSC 382456
  • NSC 382459
  • NSC-382459
  • Qapzola
  • UNII-H464ZO600O

Systematic Names

  • 1H-Indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-((1E)-3-hydroxy-1-propenyl)-1-methyl-
  • 1H-Indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-, (E)-

Registry Numbers

CAS Registry Number

  • 114560-48-4

FDA UNII

  • H464ZO600O

System Generated Number

  • 0114560484

Structure Descriptors

InChI

1S/C15H16N2O4/c1-16-10(3-2-6-18)9(8-19)13-14(16)12(20)7-11(15(13)21)17-4-5-17/h2-3,7,18-19H,4-6,8H2,1H3/b3-2+

InChIKey

MXPOCMVWFLDDLZ-NSCUHMNNSA-N

Smiles

Cn1c(c(c2c1C(=O)C=C(C2=O)N3CC3)CO)/C=C/CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 13mg/kg (13mg/kg)   European Journal of Cancer Part A. Vol. 29A, Pg. 897, 1993.
rat LD intravenous > 450ug/kg (0.45mg/kg)   European Journal of Cancer Part A. Vol. 29A, Pg. 897, 1993.