Annamycin
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Annamycin
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CAS No:
92689-49-1
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Formula:
C26H25IO11
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Chemical Name:
Annamycin
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Synonyms:
5,12-Naphthacenedione,7-[(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-,(7S,9S)-;5,12-Naphthacenedione,7-[(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-,(7S,9S)-;(7S,9S)-7-[(2,6-Dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,12-naphthacenedione;Annamycin;1195300-26-5
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CAS No:
Description
Annamycin is a lipophilic, anthracycline antineoplastic antibiotic. Annamycin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and repair as well as inhibiting RNA and protein synthesis. This agent appears to not be a substrate for the p-glycoprotein associated multidrug-resistance (MDR) transporter; therefore, overcoming the resistance pattern seen with other anthracycline compounds.
Safety Information
P201, P202, P281, P308+P313, P405, P501
H340
|Danger|H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Drug Information
Investigated for use/treatment in breast cancer and leukemia (unspecified).
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)
Annamycin belongs to the anthracycline class of drugs, and has a pleiotropic mechanism of action where it targets topoisomerase II, causing strand breaks in DNA. Annamycin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin
Computed Properties
Molecular Weight:640.4
XLogP3:2.2
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:4
Exact Mass:640.04416
Monoisotopic Mass:640.04416
Topological Polar Surface Area:191
Heavy Atom Count:38
Complexity:962
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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