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2D Structure
Also known as: Kw-2189, Pibrozelesin hbr, Pibrozelesin hydrobromide [usan], 148778-32-9, 0481jcc90t, Pibrozelesin hydrobromide (usan)
Molecular Formula
C32H37Br2N5O8
Molecular Weight
779.5  g/mol
InChI Key
YMALQNICPSISCA-GMUIIQOCSA-N
FDA UNII
0481JCC90T

Pibrozelesin Hydrobromide is the hydrobromide salt form of pibrozelesin, a semisynthetic water-soluble derivative of the antineoplastic antibiotic duocarmycin B2, with antineoplastic activity. 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.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC 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;hydrobromide
2.1.2 InChI
InChI=1S/C32H36BrN5O8.BrH/c1-16-23(31(40)45-6)25-24-18(14-33)15-38(20(24)13-21(27(25)34-16)46-32(41)37-9-7-36(2)8-10-37)30(39)19-11-17-12-22(42-3)28(43-4)29(44-5)26(17)35-19;/h11-13,18,34-35H,7-10,14-15H2,1-6H3;1H/t18-;/m1./s1
2.1.3 InChI Key
YMALQNICPSISCA-GMUIIQOCSA-N
2.1.4 Canonical SMILES
CC1=C(C2=C3C(CN(C3=CC(=C2N1)OC(=O)N4CCN(CC4)C)C(=O)C5=CC6=CC(=C(C(=C6N5)OC)OC)OC)CBr)C(=O)OC.Br
2.1.5 Isomeric SMILES
CC1=C(C2=C3[C@@H](CN(C3=CC(=C2N1)OC(=O)N4CCN(CC4)C)C(=O)C5=CC6=CC(=C(C(=C6N5)OC)OC)OC)CBr)C(=O)OC.Br
2.2 Other Identifiers
2.2.1 UNII
0481JCC90T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 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)-

2. Kw 2189

3. Kw-2189

4. 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

2.3.2 Depositor-Supplied Synonyms

1. Kw-2189

2. Pibrozelesin Hbr

3. Pibrozelesin Hydrobromide [usan]

4. 148778-32-9

5. 0481jcc90t

6. Pibrozelesin Hydrobromide (usan)

7. 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;hydrobromide

8. 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), Monohydrobromide

9. Unii-0481jcc90t

10. Chembl2106438

11. Pibrozelesin Hydrobromide [who-dd]

12. D05472

13. Q27247636

14. 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((1,6,7-trimethoxy-1h-indol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic Acid, Methyl Ester, Monohydrobromide

15. 8-(bromomethyl)-3,6,7,8-tetrahydro-2-methyl-4-(((4-methyl-1-piperazinyl)carbonyl)oxy)-6-((1,6,7-trimethoxy-1h-indol-2-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrole-1-carboxylic Acid,-, Methyl Ester, Monohydrobromide

16. 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, Hydrobromide (1:1)

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 779.5 g/mol
Molecular Formula C32H37Br2N5O8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count9
Exact Mass779.09884 g/mol
Monoisotopic Mass777.10089 g/mol
Topological Polar Surface Area139 Ų
Heavy Atom Count47
Formal Charge0
Complexity1130
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)


Antineoplastic Agents, Alkylating

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.)


Antineoplastic Agents, Hormonal

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.)