WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200200
CAS#: 150091-68-2 (2HCl)
Description: Amonafide dihydrochloride is the dihydrochloride salt of amonafide, 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.
MedKoo Cat#: 200200
Name: Amonafide dihydrochloride
CAS#: 150091-68-2 (2HCl)
Chemical Formula: C16H19Cl2N3O2
Molecular Weight: 283.32508
Elemental Analysis: C, 53.94; H, 5.38; Cl, 19.90; N, 11.80; O, 8.98
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Synonym: amonafide; amonafide hydrochloride; benzisoquinolinedione; nafidimide. US brand name: Quinamed. Abbreviations: AMON. BIDA. Code name: MFA142.
IUPAC/Chemical Name: 5-amino-2-(2-(dimethylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione dihydrochloride
InChi Key: AEMLYYQEBPJIEO-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H17N3O2.2ClH/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;2*1H
SMILES Code: O=C1N(CCN(C)C)C(C2=CC(N)=CC3=CC=CC1=C23)=O.[H]Cl.[H]Cl
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, not in water
Shelf Life: >5 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: 2934.99.9001
The following data is based on the product molecular weight 283.32508 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.
|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: Chen Z, Liang X, Zhang H, Xie H, Liu J, Xu Y, Zhu W, Wang Y, Wang X, Tan S, Kuang D, Qian X. A new class of naphthalimide-based antitumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis. J Med Chem. 2010 Mar 25;53(6):2589-600. PubMed PMID: 20170164.
2: Lv M, Xu H. Overview of naphthalimide analogs as anticancer agents. Curr Med Chem. 2009;16(36):4797-813. Review. PubMed PMID: 19929786.
3: Zhu H, Miao ZH, Huang M, Feng JM, Zhang ZX, Lu JJ, Cai YJ, Tong LJ, Xu YF, Qian XH, Ding J. Naphthalimides induce G(2) arrest through the ATM-activated Chk2-executed pathway in HCT116 cells. Neoplasia. 2009 Nov;11(11):1226-34. PubMed PMID: 19881958; PubMed Central PMCID: PMC2767224.
4: Mei ZH, Tian ZY, Ma HX, Xie SQ, Zhao J, Wang CJ. [Synthesis and in vitro cytotoxicity of naphthalimide polyamine conjugates as antitumor agents]. Yao Xue Xue Bao. 2009 Jul;44(7):754-7. Chinese. PubMed PMID: 19806915.
5: Allen SL, Kolitz JE, Lundberg AS, Bennett JM, Capizzi RL, Budman DR. Phase I trials of amonafide as monotherapy and in combination with cytarabine in patients with poor-risk acute myeloid leukemia. Leuk Res. 2010 Apr;34(4):487-91. Epub 2009 Sep 12. PubMed PMID: 19748672.
6: Wu A, Xu Y, Qian X, Wang J, Liu J. Novel naphthalimide derivatives as potential apoptosis-inducing agents: design, synthesis and biological evaluation. Eur J Med Chem. 2009 Nov;44(11):4674-80. Epub 2009 Jul 16. PubMed PMID: 19643513.
7: Wang J, Wu A, Xu Y, Liu J, Qian X. M(2)-A induces apoptosis and G(2)-M arrest via inhibiting PI3K/Akt pathway in HL60 cells. Cancer Lett. 2009 Oct 8;283(2):193-202. Epub 2009 May 10. PubMed PMID: 19435648.
8: Ingrassia L, Lefranc F, Kiss R, Mijatovic T. Naphthalimides and azonafides as promising anti-cancer agents. Curr Med Chem. 2009;16(10):1192-213. Review. PubMed PMID: 19355879.
9: Tallman M. Existing and emerging therapeutic options for the treatment of acute myeloid leukemia. Clin Adv Hematol Oncol. 2008 Nov;6(11):3-5. PubMed PMID: 19205108.
10: Xie L, Xu Y, Wang F, Liu J, Qian X, Cui J. Synthesis of new amonafide analogues via coupling reaction and their cytotoxic evaluation and DNA-binding studies. Bioorg Med Chem. 2009 Jan 15;17(2):804-10. Epub 2008 Nov 27. PubMed PMID: 19070496.