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Home > Encyclopedia > APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)-

APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)-

APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)- structure

APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)- 

structure
  • CAS No:

    114560-48-4

  • Formula:

    C15H16N2O4

  • Chemical Name:

    APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)-

  • Synonyms:

    APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)-;EO 9;5-(1-aziridinyl)-3-(hydroxyMethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-Methyl-1H-indole-4,7-dione;5-(1-Aziridinyl)-3-(hydroxymethyl)-2-[(1E)-3-hydroxy-1-propen-1-yl]-1-methyl-1H-indole-4,7-dione;EO 9 (pharmaceutical);NSC 382456;NSC 382459;(E)-5-(aziridin-1-yl)-3-(hydroxymethyl)-2-(3-hydroxyprop-1-en-1-yl)-1-methyl-1H-indole-4,7-dione

Description

Apaziquone is a member of indoles.|Apaziquone has been investigated for the treatment of Bladder Cancer and Bladder Neoplasms.|Apaziquone is 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 selectivity 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.


ChEBI: Apaziquone is a member of indoles.

APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)- Basic Attributes

288.301

288.30

H464ZO600O

382459

C1087

Characteristics

82.54000

-1.36

1.45

632.3±55.0 °C(Predicted)

336.2±31.5 °C

1.682

13.58±0.10(Predicted)

Drug Information

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

3-hydroxymethyl-5-aziridinyl-1-methyl-2-(1H-indole-4,7-dione)prop-beta-en-alpha-ol

APAZIQUONE,1H-INDOLE-4,7-DIONE, 5-(1-AZIRIDINYL)-3-(HYDROXYMETHYL)-2-(3-HYDROXY-1-PROPENYL)-1-METHYL-, (E)- Use and Manufacturing

Apaziquone is an indolequinone that is a bioreductive prodrug and a chemical analog of Mitomycin C (M371900), a chemotherapeutic agent. Apaziquone is a potential therapeutic agent for the treatment of non-muscle invasive bladder cancer.

Computed Properties

Molecular Weight:288.30
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:288.11100700
Monoisotopic Mass:288.11100700
Topological Polar Surface Area:82.5
Heavy Atom Count:21
Complexity:524
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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