WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H573805
CAS#: 51264-14-3 (free base)
Description: Amsacrine is an aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.
Hodoodo Cat#: H573805
Name: Amsacrine
CAS#: 51264-14-3 (free base)
Chemical Formula: C21H19N3O3S
Exact Mass: 393.11
Molecular Weight: 393.460
Elemental Analysis: C, 64.11; H, 4.87; N, 10.68; O, 12.20; S, 8.15
Related CAS #: 54301-16-5 (mesylate) 80277-11-8 (lactate) 54301-15-4 (HCl) 80277-07-2 (gluconate) 51264-14-3 (free base)
Synonym: Acridinylanisidide, AMSA, Amsacrine, Amsidine, Amsidyl, CI 880, CI880, CI-880, m-AMSA, meta-Amsacrine
IUPAC/Chemical Name: Methanesulfon-m-anisidide, 4'-(9-acridinylamino)-
InChi Key: XCPGHVQEEXUHNC-UHFFFAOYSA-N
InChi Code: 1S/C21H19N3O3S/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)
SMILES Code: COc1cc(ccc1Nc2c3ccccc3nc4c2cccc4)NS(=O)(=O)C
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: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 393.46 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
