Amonafide - CAS 69408-81-7
Catalog number: B0084-097145
Category: Inhibitor
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Molecular Formula:
C16H17N3O2
Molecular Weight:
283.33
COA:
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Targets:
Topoisomerase
Description:
Amonafide is an imide derivative of naphthalic acid. Amonafide intercalates into DNA and inhibits topoisomerase II, resulting in protein-associated strand breaks and impaired DNA and RNA synthesis.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-097145 50 mg $168 In stock
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Purity:
0.98
Appearance:
Light yellow to yellow solid
Synonyms:
Nafidimide; Quinamed; Xanafide
MSDS:
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InChIKey:
UPALIKSFLSVKIS-UHFFFAOYSA-N
InChI:
InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3
Canonical SMILES:
CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)N
Current Developer:
Abbott (Originator), ChemGenex Therapeutics
1.Naphthalimides as anti-cancer agents: synthesis and biological activity.
Braña MF;Ramos A Curr Med Chem Anticancer Agents. 2001 Nov;1(3):237-55.
Naphthalimides are a class of compounds with high antitumor activity upon a variety of murine and human tumor cells. These compounds bind to DNA by intercalation of the chromophore and two of them, mitonafide and amonafide, were used in clinical trials. The therapeutic properties of these lead drugs were improved by designing bisintercalating agents. One of these, elinafide, showed intense in vitro and in vivo activity and is currently being used in clinical trials against solid tumors. In this paper, the history of elinafide is described.
2.Novel agents and regimens for acute myeloid leukemia: 2009 ASH annual meeting highlights.
Zhu X;Ma Y;Liu D J Hematol Oncol. 2010 Apr 23;3:17. doi: 10.1186/1756-8722-3-17.
Prognostic markers, such as NPM1, Flt3-ITD, and cytogenetic abnormalities have made it possible to formulate aggressive treatment plans for unfavorable acute myeloid leukemia (AML). However, the long-term survival of AML with unfavorable factors remains unsatisfactory. The latest data indicate that the standard dose of daunorubicin (DNR) at 45 mg/m2 is inferior to high dose 90 mg/m2 for induction therapy. The rates of complete remission and overall survival are significantly better in the high dose induction regimen. New regimens exploring the new liposomal encapsulation of Ara-C and DNR as well as addition of gemtuzumab ozogamicin monoclonal antibody have been studied. New agents, including the nucleoside analogues (clofarabine, sapacitabine, elacytarabine), FLT3 inhibitor (sorafenib), farnesyl-transferase inhibitor (tipifarnib), histone deacetylase inhibitor (vorinostat), lenalidomide, as well as DNA methyltransferase inhibitors (decitabine, azacitidine), were recently reported for AML treatment in the 2009 ASH annual meeting. This review also summarizes the updates of the clinical trials on novel agents including voreloxin, AS1413, behenoylara-C, ARRY520, ribavirin, AZD1152, AZD6244, and terameprocol (EM-1421) from the 2009 ASH annual meeting.
3.Topoisomerase II-mediated DNA cleavage by amonafide and its structural analogs.
Hsiang YH;Jiang JB;Liu LF Mol Pharmacol. 1989 Sep;36(3):371-6.
Treatment of SV40-infected monkey cells with amonafide (benzisoquinolinedione), an intercalative antitumor drug, resulted in rapid accumulation of linearized intracellular SV40 DNA molecules that were protein linked. Studies using purified mammalian DNA topoisomerase II have shown that amonafide and its structural analogs interfere with the breakage-rejoining reaction of the enzyme by stabilizing a reversible enzyme-DNA "cleavable complex." Denaturation of the cleavable complex with sodium dodecyl sulfate resulted in DNA cleavage and the covalent association of topoisomerase II polypeptides with the cleaved DNA. Unwinding measurements indicate that amonafide is a DNA intercalator. These results suggest that amonafide and its structural analogs (e.g., mitonafide) represent a new class of intercalative topoisomerase II-active antitumor drugs. Different from other topoisomerase II-active antitumor drugs, amonafide and mitonafide induce specific DNA cleavage at a single major site on pBR322 DNA. The strong site specificity of amonafide may allow detailed characterization of the intercalator-stabilized, topoisomerase II-DNA cleavable complex.
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CAS 69408-81-7 Amonafide

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