Nitracrine dihydrochloride monohydrate | CAS# 55429-45-3 | Biochemical

MedKoo Cat#: 578211 | Name: Nitracrine dihydrochloride monohydrate

Description:

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

Nitracrine dihydrochloride monohydrate is an acridine antineoplastic agent used in mammary and ovarian tumors. It inhibits RNA synthesis.

Chemical Structure

Nitracrine dihydrochloride monohydrate

CAS#55429-45-3

Theoretical Analysis

MedKoo Cat#: 578211

Name: Nitracrine dihydrochloride monohydrate

CAS#: 55429-45-3

Chemical Formula: C18H24Cl2N4O3

Exact Mass: 414.1225

Molecular Weight: 415.31

Elemental Analysis: C, 52.06; H, 5.82; Cl, 17.07; N, 13.49; O, 11.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

C-283; C 283; C283; Ledakrin; Nitracrine dihydrochloride monohydrate; Nitracrine dihydrochloride hydrate; Nitracrine 2HCl monohydrate

IUPAC/Chemical Name

N1,N1-dimethyl-N3-(1-nitroacridin-9-yl)propane-1,3-diamine dihydrochloride hydrate

InChi Key

NHZMLGQMVDPHND-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H20N4O2.2ClH.H2O/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);2*1H;1H2

SMILES Code

O.Cl.Cl.CN(C)CCCNc1c2ccccc2nc3cccc(c13)[N+](=O)[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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 415.31 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

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.