MedKoo Cat#: 563930 | Name: Amonafide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amonafide is a topoisomerase II (Topo II) inhibitor and DNA intercalator, inducing apoptotic signaling by blocking the binding of Topo II to DNA.

Chemical Structure

Amonafide
Amonafide
CAS#69408-81-7 (free base)

Theoretical Analysis

MedKoo Cat#: 563930

Name: Amonafide

CAS#: 69408-81-7 (free base)

Chemical Formula: C16H17N3O2

Exact Mass: 283.1321

Molecular Weight: 283.33

Elemental Analysis: C, 67.83; H, 6.05; N, 14.83; O, 11.29

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
50mg USD 650.00 2 Weeks
100mg USD 950.00 2 Weeks
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Synonym
Amonafide; Nafidimide; Benzisoquinolinedione; Quinamed; Xanafide
IUPAC/Chemical Name
5-Amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione
InChi Key
UPALIKSFLSVKIS-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1N(CCN(C)C)C(C2=CC(N)=CC3=CC=CC1=C23)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 283.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Allen SL, Lundberg AS. Amonafide: a potential role in treating acute myeloid leukemia. Expert Opin Investig Drugs. 2011 Jul;20(7):995-1003. doi: 10.1517/13543784.2011.585756. Epub 2011 May 19. PMID: 21591994. 2: Xia J, Zhou Y, He S, Vashisth MK, Jia H, Dai Q, He Y, Wang X. Amonafide Induces HUVEC Senescence by Inhibiting Autophagy. Discov Med. 2023 Jun;35(176):264-274. doi: 10.24976/Discov.Med.202335176.27. PMID: 37272093. 3: Freeman CL, Swords R, Giles FJ. Amonafide: a future in treatment of resistant and secondary acute myeloid leukemia? Expert Rev Hematol. 2012 Feb;5(1):17-26. doi: 10.1586/ehm.11.68. PMID: 22272701. 4: Chau M, Christensen JL, Ajami AM, Capizzi RL. Amonafide, a topoisomerase II inhibitor, is unaffected by P-glycoprotein-mediated efflux. Leuk Res. 2008 Mar;32(3):465-73. doi: 10.1016/j.leukres.2007.07.017. Epub 2007 Sep 10. PMID: 17826829. 5: Ye Y, Huang S, Wu Y. UNBS5162 and amonafide inhibits tumor progression in human melanoma by the AKT/mTOR pathway. Cancer Manag Res. 2019 Mar 22;11:2339-2348. doi: 10.2147/CMAR.S177623. PMID: 30962721; PMCID: PMC6434921. 6: Zhao J, Lu M, Lai H, Lu H, Lalevée J, Barner-Kowollik C, Stenzel MH, Xiao P. Delivery of Amonafide from Fructose-Coated Nanodiamonds by Oxime Ligation for the Treatment of Human Breast Cancer. Biomacromolecules. 2018 Feb 12;19(2):481-489. doi: 10.1021/acs.biomac.7b01592. Epub 2018 Jan 23. PMID: 29316394. 7: Norton JT, Witschi MA, Luong L, Kawamura A, Ghosh S, Stack MS, Sim E, Avram MJ, Appella DH, Huang S. Synthesis and anticancer activities of 6-amino amonafide derivatives. Anticancer Drugs. 2008 Jan;19(1):23-36. doi: 10.1097/CAD.0b013e3282f00e17. PMID: 18043127. 8: Innocenti F, Iyer L, Ratain MJ. Pharmacogenetics of anticancer agents: lessons from amonafide and irinotecan. Drug Metab Dispos. 2001 Apr;29(4 Pt 2):596-600. PMID: 11259359. 9: Ratain MJ, Rosner G, Allen SL, Costanza M, Van Echo DA, Henderson IC, Schilsky RL. Population pharmacodynamic study of amonafide: a Cancer and Leukemia Group B study. J Clin Oncol. 1995 Mar;13(3):741-7. doi: 10.1200/JCO.1995.13.3.741. PMID: 7884434. 10: Ratain MJ, Mick R, Berezin F, Janisch L, Schilsky RL, Vogelzang NJ, Lane LB. Phase I study of amonafide dosing based on acetylator phenotype. Cancer Res. 1993 May 15;53(10 Suppl):2304-8. PMID: 8485716. 11: De Isabella P, Zunino F, Capranico G. Base sequence determinants of amonafide stimulation of topoisomerase II DNA cleavage. Nucleic Acids Res. 1995 Jan 25;23(2):223-9. doi: 10.1093/nar/23.2.223. PMID: 7862525; PMCID: PMC306658. 12: Ratain MJ, Mick R, Berezin F, Janisch L, Schilsky RL, Williams SF, Smiddy J. Paradoxical relationship between acetylator phenotype and amonafide toxicity. Clin Pharmacol Ther. 1991 Nov;50(5 Pt 1):573-9. doi: 10.1038/clpt.1991.183. PMID: 1934870. 13: Zhu H, Huang M, Yang F, Chen Y, Miao ZH, Qian XH, Xu YF, Qin YX, Luo HB, Shen X, Geng MY, Cai YJ, Ding J. R16, a novel amonafide analogue, induces apoptosis and G2-M arrest via poisoning topoisomerase II. Mol Cancer Ther. 2007 Feb;6(2):484-95. doi: 10.1158/1535-7163.MCT-06-0584. PMID: 17308047. 14: Xie LJ. 5-Butyl-amino-2-[2-(dimethyl-amino)eth- yl]-1H-benz[de]isoquinoline-1,3(2H)-dione. Acta Crystallogr Sect E Struct Rep Online. 2010 May 26;66(Pt 6):o1454. doi: 10.1107/S1600536810018702. PMID: 21579523; PMCID: PMC2979579. 15: Hsiang YH, Jiang JB, Liu LF. Topoisomerase II-mediated DNA cleavage by amonafide and its structural analogs. Mol Pharmacol. 1989 Sep;36(3):371-6. PMID: 2550774. 16: Liu Y, Norton JT, Witschi MA, Xu Q, Lou G, Wang C, Appella DH, Chen Z, Huang S. Methoxyethylamino-numonafide is an efficacious and minimally toxic amonafide derivative in murine models of human cancer. Neoplasia. 2011 May;13(5):453-60. doi: 10.1593/neo.101738. PMID: 21532886; PMCID: PMC3084622. 17: Felder TB, McLean MA, Vestal ML, Lu K, Farquhar D, Legha SS, Shah R, Newman RA. Pharmacokinetics and metabolism of the antitumor drug amonafide (NSC-308847) in humans. Drug Metab Dispos. 1987 Nov-Dec;15(6):773-8. PMID: 2893701. 18: Wang Y, Zhang J, Li M, Li M, Xie S, Wang C. Synthesis and evaluation of novel amonafide-polyamine conjugates as anticancer agents. Chem Biol Drug Des. 2017 May;89(5):670-680. doi: 10.1111/cbdd.12888. Epub 2016 Nov 19. PMID: 27762101. 19: Kornek G, Raderer M, Depisch D, Haider K, Fazeny B, Dittrich C, Scheithauer W. Amonafide as first-line chemotherapy for metastatic breast cancer. Eur J Cancer. 1994;30A(3):398-400. doi: 10.1016/0959-8049(94)90264-x. PMID: 8204367. 20: Saez R, Craig JB, Kuhn JG, Weiss GR, Koeller J, Phillips J, Havlin K, Harman G, Hardy J, Melink TJ, et al. Phase I clinical investigation of amonafide. J Clin Oncol. 1989 Sep;7(9):1351-8. doi: 10.1200/JCO.1989.7.9.1351. PMID: 2549205.