Synonym: acridinyl anisidide; Cains Acridine. US brand name: Amsa PD. Foreign brand names: Amekrin; Amsidine; Amsidyl; Lamasine. Abbreviations: AMSA; mAMSA. Code names: CI880; SN11841.

IUPAC/Chemical Name: N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide hydrochloride

InChi Key: WDISRLXRMMTXEV-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H19N3O3S.ClH/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21;/h4-13,24H,1-2H3,(H,22,23);1H

SMILES Code: CS(=O)(NC1=CC=C(NC2=C(C=CC=C3)C3=NC4=CC=CC=C42)C(OC)=C1)=O.[H]Cl

Technical Data

Additional Information

Related:
51264-14-3 (Amsacrine)
54301-15-4 (Amsacrine HCl).

References

1: Jangir DK, Kundu S, Mehrotra R. Role of minor groove width and hydration pattern on amsacrine interaction with DNA. PLoS One. 2013 Jul 29;8(7):e69933. doi: 10.1371/journal.pone.0069933. Print 2013. PubMed PMID: 23922861; PubMed Central PMCID: PMC3726726.

2: Krejci M, Doubek M, Dusek J, Brychtova Y, Racil Z, Navratil M, Tomiska M, Horky O, Pospisilova S, Mayer J. Combination of fludarabine, amsacrine, and cytarabine followed by reduced-intensity conditioning and allogeneic hematopoietic stem cell transplantation in patients with high-risk acute myeloid leukemia. Ann Hematol. 2013 Jun 1. [Epub ahead of print] PubMed PMID: 23728608.

3: Schaich M, Parmentier S, Kramer M, Illmer T, Stölzel F, Röllig C, Thiede C, Hänel M, Schäfer-Eckart K, Aulitzky W, Einsele H, Ho AD, Serve H, Berdel WE, Mayer J, Schmitz N, Krause SW, Neubauer A, Baldus CD, Schetelig J, Bornhäuser M, Ehninger G. High-dose cytarabine consolidation with or without additional amsacrine and mitoxantrone in acute myeloid leukemia: results of the prospective randomized AML2003 trial. J Clin Oncol. 2013 Jun 10;31(17):2094-102. doi: 10.1200/JCO.2012.46.4743. Epub 2013 Apr 29. PubMed PMID: 23630210.

4: Fong CY, Grigoriadis G, Hocking J, Coutsouvelis J, Muirhead J, Campbell P, Paul E, Walker P, Avery S, Patil S, Spencer A, Schwarer A, Wei A. Fludarabine, cytarabine, granulocyte-colony stimulating factor and amsacrine: an effective salvage therapy option for acute myeloid leukemia at first relapse. Leuk Lymphoma. 2013 Feb;54(2):336-41. doi: 10.3109/10428194.2012.713479. Epub 2012 Sep 8. PubMed PMID: 22812445.

5: Jangir DK, Dey SK, Kundu S, Mehrotra R. Assessment of amsacrine binding with DNA using UV-visible, circular dichroism and Raman spectroscopic techniques. J Photochem Photobiol B. 2012 Sep 3;114:38-43. doi: 10.1016/j.jphotobiol.2012.05.005. Epub 2012 May 18. PubMed PMID: 22677564.

6: Ketron AC, Denny WA, Graves DE, Osheroff N. Amsacrine as a topoisomerase II poison: importance of drug-DNA interactions. Biochemistry. 2012 Feb 28;51(8):1730-9. doi: 10.1021/bi201159b. Epub 2012 Feb 10. PubMed PMID: 22304499; PubMed Central PMCID: PMC3289736.

7: Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. J Appl Toxicol. 2013 Jun;33(6):426-33. doi: 10.1002/jat.1753. Epub 2011 Nov 11. PubMed PMID: 22081495.

8: Devi ML, Chandrasekhar KB, Surendranath KV, Rao BM, Narayana MB. A validated stability-indicating RP-HPLC assay method for Amsacrine and its related substances. J Chromatogr Sci. 2011 Aug;49(7):489-94. PubMed PMID: 21801478.

9: Wilhelm C, Neubauer A, Burchert A. Poor-risk cytogenetics may be associated with inferior outcome after fludarabine, cytarabine, and amsacrine reduced intensity conditioning in patients with high-risk acute myeloid leukemia. Leuk Lymphoma. 2011 Oct;52(10):2031-5. doi: 10.3109/10428194.2011.588760. Epub 2011 Jun 24. PubMed PMID: 21702642.

10: Zhang L, Guo Y, Wang J, Wang X, Han G, Ou W, Xu Y, Zhang X. Assisted sonodynamic damage of bovine serum albumin by metronidazole under ultrasonic irradiation combined with photosensitive antitumor drug-Amsacrine. J Photochem Photobiol B. 2010 Jan 21;98(1):61-8. doi: 10.1016/j.jphotobiol.2009.11.005. Epub 2009 Nov 22. PubMed PMID: 20006932.