Amsacrine HCl

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

Description:Amsacrine is an aminoacridine derivative with potential antineoplastic activity. Although its mechanism of action is incompletely defined, amsacrine may intercalate into DNA and inhibit topoisomerase II, resulting in DNA double-strand breaks, arrest of the S/G2 phase of the cell cycle, and cell death. This agent's cytotoxicity is maximal during the S phase of the cell cycle when topoisomerase levels are greatest. In addition, amsacrine may induce transcription of tumor promoter p53 protein and block p53 ubiquitination and proteasomal degradation, resulting in p53-dependent tumor cell apoptosis.

Price and Availability

Amsacrine HCl, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 100057Name: Amsacrine HClCAS#: 54301-15-4 (HCl)Chemical Formula: C21H20ClN3O3SExact Mass: Molecular Weight: 429.92Elemental Analysis: C, 58.67; H, 4.69; Cl, 8.25; N, 9.77; O, 11.16; S, 7.46

Related CAS #:51264-14-3 (free base)54301-16-5 (mesylate)80277-07-2 (gluconate)80277-11-8 (lactate)54301-15-4 (HCl)

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;/h3-13,24H,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 minorgroove 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 andallogeneic hematopoietic stem cell transplantation in patients withhigh-risk acute myeloid leukemia. Ann Hematol. 2013 Jun 1. [Epub aheadof 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, ServeH, Berdel WE, Mayer J, Schmitz N, Krause SW, Neubauer A, Baldus CD,Schetelig J, Bornhäuser M, Ehninger G. High-dose cytarabineconsolidation with or without additional amsacrine and mitoxantrone inacute myeloid leukemia: results of the prospective randomized AML2003trial. 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 factorand amsacrine: an effective salvage therapy option for acute myeloidleukemia 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 amsacrinebinding with DNA using UV-visible, circular dichroism and Ramanspectroscopic 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 atopoisomerase II poison: importance of drug-DNA interactions.Biochemistry. 2012 Feb 28;51(8):1730-9. doi: 10.1021/bi201159b. Epub2012 Feb 10. PubMed PMID: 22304499; PubMed Central PMCID: PMC3289736.

7: Attia SM. Molecular cytogenetic evaluation of the mechanism ofgenotoxic potential of amsacrine and nocodazole in mouse bone marrowcells. 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. Avalidated stability-indicating RP-HPLC assay method for Amsacrine andits related substances. J Chromatogr Sci. 2011 Aug;49(7):489-94. PubMedPMID: 21801478.

9: Wilhelm C, Neubauer A, Burchert A. Poor-risk cytogenetics may beassociated with inferior outcome after fludarabine, cytarabine, andamsacrine reduced intensity conditioning in patients with high-riskacute 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. Assistedsonodynamic damage of bovine serum albumin by metronidazole underultrasonic 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.