Ametantrone
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MedKoo CAT#: 200182

CAS#: 64862-96-0

Description: Ametantrone (AM) is a synthetic 9,10-anthracenedione bearing two (hydroxyethylamino)ethylamino residues at positions 1 and 4; along with other anthraquinones and anthracyclines, it shares a polycyclic intercalating moiety and charged side chains that stabilize DNA binding. Ametantrone is the second anthracene derivative to enter clinical trials.

Chemical Structure

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Ametantrone
CAS# 64862-96-0
Instruction

Theoretical Analysis

MedKoo Cat#: 200182
Name: Ametantrone
CAS#: 64862-96-0
Chemical Formula: C22H28N4O4
Exact Mass: 412.21
Molecular Weight: 412.480
Elemental Analysis: C, 64.06; H, 6.84; N, 13.58; O, 15.52

Price and Availability

Size Price Availability Quantity
5mg USD 315
10mg USD 585
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Synonym: CI881; NSC196473; NSC 287513; NSC-196473; NSC 287513; ametantrone diacetate.

IUPAC/Chemical Name: 1,4-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione

InChi Key: FFGSXKJJVBXWCY-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H28N4O4/c27-13-11-23-7-9-25-17-5-6-18(26-10-8-24-12-14-28)20-19(17)21(29)15-3-1-2-4-16(15)22(20)30/h1-6,23-28H,7-14H2

SMILES Code: O=C1C2=C(C=CC=C2)C(C3=C(NCCNCCO)C=CC(NCCNCCO)=C13)=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, 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

More Info: Ametantrone is anticancer drug candidate targeting DNA. Ametantrone induces interstrand DNA cross-links in HeLa S3 cells. These cross-links were observed only in cellular system suggesting that metabolism of the drugs is a necessary step leading to DNA cross-linking. Biologically inactive analogue of mitoxantrone, compound NSC 321458, did not induce cross-links in DNA of tumour cells which suggests that DNA cross-linking is associated with the cytotoxic and anti-tumour activity of these compounds. Source: Br J Cancer. 2000 Apr;82(7):1300-4. or  http://www.ncbi.nlm.nih.gov/pubmed/10755405.   Current developer:       

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 412.48 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Schabel FM Jr, Corbett TH, Griswold DP Jr, Laster WR Jr, Trader MW. Therapeutic activity of mitoxantrone and ametantrone against murine tumors. Cancer Treat Rev. 1983 Dec;10 Suppl B:13-21. doi: 10.1016/0305-7372(83)90017-8. PMID: 6362874.


2: Artigas G, López-Senín P, González C, Escaja N, Marchán V. Ametantrone-based compounds as potential regulators of Tau pre-mRNA alternative splicing. Org Biomol Chem. 2015 Jan 14;13(2):452-64. doi: 10.1039/c4ob01925c. Epub 2014 Nov 5. PMID: 25372055.


3: Zagotto G, Gianoncelli A, Sissi C, Marzano C, Gandin V, Pasquale R, Capranico G, Ribaudo G, Palumbo M. Novel ametantrone-amsacrine related hybrids as topoisomerase IIβ poisons and cytotoxic agents. Arch Pharm (Weinheim). 2014 Oct;347(10):728-37. doi: 10.1002/ardp.201400111. Epub 2014 Jul 17. PMID: 25042690.


4: Kuhn JG, Balmer CE, Ludden TM, Loesch DM, Von Hoff DD, Bender JF, Grillo- Lopez AJ. Pharmacokinetics of ametantrone acetate (NSC-287513). Cancer Chemother Pharmacol. 1987;19(2):133-7. doi: 10.1007/BF00254565. PMID: 3568271.


5: Artigas G, Marchán V. Synthesis and tau RNA binding evaluation of ametantrone-containing ligands. J Org Chem. 2015 Feb 20;80(4):2155-64. doi: 10.1021/jo502661j. Epub 2015 Jan 29. PMID: 25602935.


6: Kharasch ED, Novak RF. Mitoxantrone and ametantrone inhibit hydroperoxide- dependent initiation and propagation reactions in fatty acid peroxidation. J Biol Chem. 1985 Sep 5;260(19):10645-52. PMID: 2993283.


7: Yang XL, Robinson H, Gao YG, Wang AH. Binding of a macrocyclic bisacridine and ametantrone to CGTACG involves similar unusual intercalation platforms. Biochemistry. 2000 Sep 12;39(36):10950-7. PMID: 10998231.


8: Jamison JM, Krabill K, Flowers DG, Tsai C. Enhancement of the antiviral activity of poly r(A-U) by ametantrone and mitoxantrone. Life Sci. 1990;46(9):653-61. doi: 10.1016/0024-3205(90)90134-d. PMID: 2155366.


9: Kolodziejczyk P, Garnier-Suillerot A. Circular dichroism study of the interaction of mitoxantrone, ametantrone and their Pd(II) complexes with deoxyribonucleic acid. Biochim Biophys Acta. 1987 Dec 7;926(3):249-57. doi: 10.1016/0304-4165(87)90210-8. PMID: 3689823.


10: Skladanowski A, Konopa J. Mitoxantrone and ametantrone induce interstrand cross-links in DNA of tumour cells. Br J Cancer. 2000 Apr;82(7):1300-4. doi: 10.1054/bjoc.1999.1095. PMID: 10755405; PMCID: PMC2374491.


11: Kapuscinski J, Darzynkiewicz Z. Interactions of antitumor agents Ametantrone and Mitoxantrone (Novatrone) with double-stranded DNA. Biochem Pharmacol. 1985 Dec 15;34(24):4203-13. doi: 10.1016/0006-2952(85)90275-8. PMID: 4074383.


12: Dackiewicz P, Skladanowski A, Konopa J. 32P-postlabelling analysis of adducts formed by mitoxantrone and ametantrone with DNA and homopolydeoxyribonucleotides after enzymatic activation. Chem Biol Interact. 1995 Nov 17;98(2):153-66. doi: 10.1016/0009-2797(95)03643-1. PMID: 8548855.


13: Thiry M, Jamison JM, Gilloteaux J, Summers JL, Goessens G. Ultrastructural nucleolar alterations induced by an ametantrone/polyr(A-U) complex. Exp Cell Res. 1997 Oct 10;236(1):275-84. doi: 10.1006/excr.1997.3743. PMID: 9344608.


14: Kapuscinski J, Darzynkiewicz Z. Relationship between the pharmacological activity of antitumor drugs Ametantrone and mitoxantrone (Novatrone) and their ability to condense nucleic acids. Proc Natl Acad Sci U S A. 1986 Sep;83(17):6302-6. doi: 10.1073/pnas.83.17.6302. PMID: 3462696; PMCID: PMC386491.


15: Denny WA, Wakelin LP. Kinetics of the binding of mitoxantrone, ametantrone and analogues to DNA: relationship with binding mode and anti-tumour activity. Anticancer Drug Des. 1990 May;5(2):189-200. PMID: 2357264.


16: Kharasch ED, Wendel NK, Novak RF. Anthracenedione antineoplastic agent effects on drug metabolism in vitro and in vivo: relationship between structure and mechanism of inhibition. Fundam Appl Toxicol. 1987 Jul;9(1):18-25. doi: 10.1016/0272-0590(87)90149-7. PMID: 3114031.


17: al-Gailany KA, Alwan AH. Interactions of the anti-tumor ametantrone and mitoxantrone with rat hepatic microsomes. Biochem Pharmacol. 1988 Oct 15;37(20):3803-6. doi: 10.1016/0006-2952(88)90059-7. PMID: 3142480.


18: Cheemalamarri C, Batchu UR, Thallamapuram NP, Katragadda SB, Reddy Shetty P. A review on hydroxy anthraquinones from bacteria: crosstalk's of structures and biological activities. Nat Prod Res. 2022 Dec;36(23):6186-6205. doi: 10.1080/14786419.2022.2039920. Epub 2022 Feb 17. PMID: 35175877.


19: Rozencweig M, Sanders C, Rombaut W, Crespeigne N, Kenis Y, Klastersky J. Phase II study of ametantrone in a human tumor cloning assay. Eur J Cancer Clin Oncol. 1985 Feb;21(2):195-8. doi: 10.1016/0277-5379(85)90173-7. PMID: 3987756.


20: Loesch DM, Von Hoff DD, Kuhn J, Coltman CA, Tio F, Chaudhuri TK, Bender JF, Grillo-Lopez AJ. Phase I investigation of ametantrone. Cancer Treat Rep. 1983 Nov;67(11):987-91. PMID: 6640557.