Nitracrine (free base)

Orders received during 11/25~11/29 will be shipped in 11/30/2020 due to Thanksgiving holiday.

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

MedKoo CAT#: 584319

CAS#: 4533-39-5 (free base)

Description: Nitracrine (free base) is an acridine antineoplastic agent used in mammary and ovarian tumors. It inhibits RNA synthesis.


Price and Availability

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Pricing updated 2020-11-25. Prices are subject to change without notice.

Nitracrine (free base) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584319
Name: Nitracrine (free base)
CAS#: 4533-39-5 (free base)
Chemical Formula: C18H20N4O2
Exact Mass: 324.1586
Molecular Weight: 324.384
Elemental Analysis: C, 66.65; H, 6.21; N, 17.27; O, 9.86


Related CAS #: 4533-39-5 (free base)   6514-85-8 (HCl)  

Synonym: Nitracrine (free base); C 283; CCRIS 1973

IUPAC/Chemical Name: 1-Nitro-9-(3'-dimethylaminopropylamino)-acridine

InChi Key: YMVWGSQGCWCDGW-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H20N4O2/c1-21(2)12-6-11-19-18-13-7-3-4-8-14(13)20-15-9-5-10-16(17(15)18)22(23)24/h3-5,7-10H,6,11-12H2,1-2H3,(H,19,20)

SMILES Code: CN(CCCNC1=C(C([N+]([O-])=O)=CC=C2)C2=NC3=CC=CC=C31)C


Technical Data

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:
>2 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


References

1: Niemira M, Dastych J, Mazerska Z. Pregnane X receptor dependent up-regulation of CYP2C9 and CYP3A4 in tumor cells by antitumor acridine agents, C-1748 and C-1305, selectively diminished under hypoxia. Biochem Pharmacol. 2013 Jul 15;86(2):231-41. doi: 10.1016/j.bcp.2013.05.008. Epub 2013 May 18. PubMed PMID: 23688499.

2: Wilson WR, Thompson LH, Anderson RF, Denny WA. Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives. J Med Chem. 1989 Jan;32(1):31-8. PubMed PMID: 2909741.

3: Siim BG, Hicks KO, Pullen SM, van Zijl PL, Denny WA, Wilson WR. Comparison of aromatic and tertiary amine N-oxides of acridine DNA intercalators as bioreductive drugs. Cytotoxicity, DNA binding, cellular uptake, and metabolism. Biochem Pharmacol. 2000 Oct 1;60(7):969-78. PubMed PMID: 10974206.

4: Szumiel I, Walicka M. Cytotoxicity and the effect of combined treatment with X-rays of an anticancer 1-nitro-9-aminoacridine derivative in L5178Y-R and L5178Y-S cells. Neoplasma. 1980;27(6):697-702. PubMed PMID: 7254425.

5: Tadi K, Ashok BT, Chen Y, Banerjee D, Wysocka-Skrzela B, Konopa J, Darzynkiewicz Z, Tiwari RK. Pre-clinical evaluation of 1-nitroacridine derived chemotherapeutic agent that has preferential cytotoxic activity towards prostate cancer. Cancer Biol Ther. 2007 Oct;6(10):1632-7. Epub 2007 Jul 24. Erratum in: Cancer Biol Ther. 2008 Mar;7(3):479. PubMed PMID: 17921700; PubMed Central PMCID: PMC4134887.

6: Robertson IG, Bland TJ, Palmer BD. Effect of substituents on the metabolism of nitracrine in rat. Xenobiotica. 1996 May;26(5):559-69. PubMed PMID: 8736066.

7: Ferguson LR, Denny WA, O'Rourke SM. Mutagenic activity of nitracrine derivatives in Salmonella typhimurium: relationship to drug physicochemical parameters, and to bacterial uvrB and recA genes and plasmid pKM101. Mutat Res. 1989 May;223(1):13-22. PubMed PMID: 2654627.

8: Wiśniewska A, Niemira M, Jagiełło K, Potęga A, Swist M, Henderson C, Skwarska A, Augustin E, Konopa J, Mazerska Z. Diminished toxicity of C-1748, 4-methyl-9-hydroxyethylamino-1-nitroacridine, compared with its demethyl analog, C-857, corresponds to its resistance to metabolism in HepG2 cells. Biochem Pharmacol. 2012 Jul 1;84(1):30-42. doi: 10.1016/j.bcp.2012.03.013. Epub 2012 Apr 6. PubMed PMID: 22484277.

9: Gniazdowski M. Mechanism of inhibition of DNA-dependent RNA synthesis in vitro by Ledakrin. Mater Med Pol. 1978 Jul-Sep;10(3):159-65. PubMed PMID: 723289.

10: Warwas M, Narczeuska B, Dobryszycka W. Blood serum peptidases in patients with ovarian carcinoma treated with Ledakrin. Arch Immunol Ther Exp (Warsz). 1977;25(2):235-42. PubMed PMID: 17375.

11: Oleszkiewicz L, Zarzycki J, Szroeder J, Dereń K. The effect of Ledacrin on elements of the lobulus in human liver. Acta Med Pol. 1979;20(4):445-6. PubMed PMID: 546115.

12: Roberts PB, Anderson RF, Wilson WR. Hypoxia-selective radiosensitization of mammalian cells by nitracrine, an electron-affinic DNA intercalator. Int J Radiat Biol Relat Stud Phys Chem Med. 1987 Apr;51(4):641-54. PubMed PMID: 3495509.

13: Kulczycka E, Krzyzowska-Gruca S, Marczyński B. Effects of some 9-aminoacridine derivatives on the nucleus and nucleolus. Ann Med Sect Pol Acad Sci. 1976;21(1-2):67-8. PubMed PMID: 952072.

14: Acheson RM, Taylor GN, Waring MJ, Haylock S, Abel G. The intercalative DNA binding and antitumor activity of some bis-acridines related to nitracrine. Chem Biol Interact. 1985 May;53(3):371-5. PubMed PMID: 4006013.

15: Radzikowski C. Antineoplastic activity of C-283 preparation (Ledakrin) in model experiments. Mater Med Pol. 1976 Jul-Sep;8(3):345-9. PubMed PMID: 1034860.

16: Ferguson LR, Turner PM, Denny WA. Mutagenicity of nitracrine analogues in Salmonella typhimurium: mutational specificity and activation by bacterial enzymes and rat-liver S9. Mutat Res. 1987 Jan;187(1):1-9. PubMed PMID: 3540655.

17: Bartoszek A, Dackiewicz P, Składanowski A, Konopa J. In vitro DNA crosslinking by Ledakrin, an antitumor derivative of 1-nitro-9-aminoacridine. Chem Biol Interact. 1997 Feb 28;103(2):141-51. PubMed PMID: 9055872.

18: Konopa J, Pawlak JW, Pawlak K. The mode of action of cytotoxic and antitumor 1-nitroacridines. III. In vivo interstrand cross-linking of DNA of mammalian or bacterial cells by 1-nitroacridines. Chem Biol Interact. 1983 Feb;43(2):175-97. PubMed PMID: 6402315.

19: Mazerska Z, Chołody M, Lukowicz J, Wysocka-Skrzela B, Ledóchowski A. Comparison of antitumor properties of nitracrine and amsacrine analogs. Arzneimittelforschung. 1987 Nov;37(11):1276-81. PubMed PMID: 3326605.

20: Daghastanli NA, Rossa MM, Selistre-De-Araujo HS, Tedesco AC, Borissevitch IE, Degterev IA. Cytotoxicity of nitroheterocyclic compounds, quinifuryl and nitracrine, towards leukaemic and normal cells on the dark and under illumination with visible light. J Photochem Photobiol B. 2004 Jul 19;75(1-2):27-32. PubMed PMID: 15246347.