methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
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methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
structure -
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CAS No:
154889-68-6
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Formula:
C32H36BrN5O8
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Chemical Name:
methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
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Synonyms:
Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (S)-;KW 2189;KW-2189;methyl(1S)-1-bromomethyl-7-methyl-5-((4-methylpiperazinyl)carbonyloxy)-3-((5,6,7-trimethoxy-2-indolyl)carbonyl)-1,2-dihydro-3H-pyrrolo(3,2-e)indole-8-carboxylate hydrobromide;PIBROZELESIN;UNII-IHK933KCIC;IHK933KCIC;154889-68-6;Benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic acid, 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (S)-;Pibrozelesin [INN];KW 2189;CHEMBL36015;SCHEMBL14499178;methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate;Methyl(1S)-1-bromomethyl-7-methyl-5-((4-methylpiperazinyl)carbonyloxy)-3-((5,6,7-trimethoxy-2-indolyl)carbonyl)-1,2-dihydro-3H-pyrrolo(3,2-e)indole-8-carboxylate hydrobromide;Q27280739;Methyl (S)-8-(bromomethyl)-3,6,7,8-tetrahydro-4-hydroxy-2-methyl-6-((5,6,7-trimethoxyindol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-1-carboxylate, 4-methyl-1-piperazinecarboxylate (ester)
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CAS No:
Description
Pibrozelesin is a semisynthetic water-soluble derivative of the antineoplastic antibiotic duocarmycin B2. Activated by carboxyl esterase, pibrozelesin alkylates DNA by binding to adenine-thymine (A-T)-rich sequences in the minor groove of DNA, thereby inhibiting DNA replication and inducing apoptosis.
methyl (8S)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate Basic Attributes
698.6 g/mol
697.17473 g/mol
IHK933KCIC
C1542
Drug Information
Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)|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')dipyrrole-1-carboxylic acid, 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (S)-
Computed Properties
Molecular Weight:698.6
XLogP3:3.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:9
Exact Mass:697.17473
Monoisotopic Mass:697.17473
Topological Polar Surface Area:139
Heavy Atom Count:46
Complexity:1130
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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