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Bizelesin

Bizelesin structure

Bizelesin 

structure
  • CAS No:

    129655-21-6

  • Formula:

    C43H36Cl2N8O5

  • Chemical Name:

    Bizelesin

  • Synonyms:

    Bizelesin;1,3-Bis[2-[[[(8S)-8β-chloromethyl-3,6,7,8-tetrahydro-4-hydroxy-1-methylbenzo[1,2-b:4,3-b']dipyrrol]-6-yl]carbonyl]-1H-indol-5-yl]urea;NSC-615291;U-77779;(8S,8'S)-6,6'-[Carbonylbis(iMino-1H-indole-5,2-diylcarbonyl)]bis[8-(chloroMethyl)-3,6,7,8-tetrahydro-1-Methylbe;N,N'-Bis[2-[[(1S)-1-(chloroMethyl)-1,6-dihydro-5-hydroxy-8-Methylbenzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]urea

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Bizelesin has been used in trials studying the treatment of Unspecified Adult Solid Tumor, Protocol Specific.|Bizelesin is a synthetic cyclopropylpyrroloindole antineoplastic antibiotic. Bizelesin binds to the minor groove of DNA and induces interstrand cross-linking of DNA, thereby inhibiting DNA replication and RNA synthesis. Bizelesin also enhances p53 and p21 induction and triggers G2/M cell-cycle arrest, resulting in cell senescence without apoptosis. (NCI04)

Bizelesin Basic Attributes

815.714

814.21900

L0O9OBI87E

615291

DTXSID00156213

C1472

Characteristics

185

9.52540

1.604g/cm3

1.856

Drug Information

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)

Benzo(1,2-b:4,3-b')dipyrrol-4-ol, 6,6'-(carbonylbis(imino-1H-indole-5,2-diylcarbonyl))bis(8-(chloromethyl)-3,6,7,8-tetrahydro-1-methyl-, (S-(R*,R*)))

Bizelesin Use and Manufacturing

As members of the cyclopropylpyrroloindole family, Adozelesin and Bizelesin cause genomic DNA lesions by alkylating DNA. Adozelesin induces single-strand DNA lesions, whereas Bizelesin induces both single-strand lesions and double-strand DNA cross-links. liferation by different pathways (i.e., Adozelesin induced apoptosis, and Bizelesin induced senescence).

Computed Properties

Molecular Weight:815.7
XLogP3:6.5
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:814.2185717
Monoisotopic Mass:814.2185717
Topological Polar Surface Area:185
Heavy Atom Count:58
Complexity:1470
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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