Nitrofurazone | CAS#59-87-0

MedKoo Cat#: 318373 | Name: Nitrofurazone

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Description:

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

Nitrofurazone is a topical anti-infective agent that is effective against gram-negative and gram-positive bacteria. It is used for superficial wounds and injuries and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis.

Chemical Structure

Nitrofurazone

CAS#59-87-0

Theoretical Analysis

MedKoo Cat#: 318373

Name: Nitrofurazone

CAS#: 59-87-0

Chemical Formula: C6H6N4O4

Exact Mass: 198.0389

Molecular Weight: 198.14

Elemental Analysis: C, 36.37; H, 3.05; N, 28.28; O, 32.30

Price and Availability

Size	Price	Availability	Quantity
10g	USD 90.00
20g	USD 150.00
50g	USD 250.00
100g	USD 450.00
200g	USD 650.00

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Related CAS #

No Data

Synonym

Nitrofurazone, Nitrofural, Furacin, Furacilin

IUPAC/Chemical Name

(E)-2-((5-nitrofuran-2-yl)methylene)hydrazinecarboxamide

InChi Key

IAIWVQXQOWNYOU-FPYGCLRLSA-N

InChi Code

InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+

SMILES Code

O=[N+]([O-])C1=CC=C(/C=N/NC(N)=O)O1

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

>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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nitrofurazone (Nitrofural) is a bactericidal compound used as an antibiotic.

In vitro activity:

Nitrofurazone significantly stimulated the proliferation of estrogen-dependent MCF-7 cells. Nitrofurazone caused Cu(II)-mediated damage to 32P-5'-end-labeled DNA fragments obtained from human genes only when cytochrome P450 reductase was added. Reference: Cancer Lett. 2004 Nov 25;215(2):141-50. https://pubmed.ncbi.nlm.nih.gov/15488632/

In vivo activity:

The antibiotic nitrofurazone (NF) has been known for its testicular toxicity; in contrast, much less is known about its effect on the liver. NF was given to male rats for up to 7 consecutive days to evaluate NF-induced effects on the liver. NF increased hepatocyte DNA synthesis and liver weight in a dose-dependent manner, with no apparent histological or biochemical evidence of cell damage or loss. Reference: Exp Toxicol Pathol. 2002 Feb;53(6):421-6. https://pubmed.ncbi.nlm.nih.gov/11926282/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	97.5	492.09

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 198.14 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:

1. Hiraku Y, Sekine A, Nabeshi H, Midorikawa K, Murata M, Kumagai Y, Kawanishi S. Mechanism of carcinogenesis induced by a veterinary antimicrobial drug, nitrofurazone, via oxidative DNA damage and cell proliferation. Cancer Lett. 2004 Nov 25;215(2):141-50. doi: 10.1016/j.canlet.2004.05.016. PMID: 15488632. 2. Ito K, Kajikawa S, Aisuke N, Hanada T, Doi K. Antioxidants suppress nitrofurazone-induced proliferation of hepatocytes. Exp Toxicol Pathol. 2003 Nov;55(4):247-50. doi: 10.1078/0940-2993-00326. PMID: 14703769. 3. Ito K, Ishida K, Takeuchi A, Nii A, Okamiya H, Doi K. Nitrofurazone induces non-regenerative hepatocyte proliferation in rats. Exp Toxicol Pathol. 2002 Feb;53(6):421-6. doi: 10.1078/0940-2993-00210. PMID: 11926282. 4. Shoda T, Yasuhara K, Moriyasu M, Takahashi T, Uneyama C, Hirose M, Mitsumori K. Testicular toxicity of nitrofurazone causing germ cell apoptosis in rats. Arch Toxicol. 2001 Jul;75(5):297-305. doi: 10.1007/s002040100231. PMID: 11548123.

In vitro protocol:

In vivo protocol:

1. Ito K, Ishida K, Takeuchi A, Nii A, Okamiya H, Doi K. Nitrofurazone induces non-regenerative hepatocyte proliferation in rats. Exp Toxicol Pathol. 2002 Feb;53(6):421-6. doi: 10.1078/0940-2993-00210. PMID: 11926282. 2. Shoda T, Yasuhara K, Moriyasu M, Takahashi T, Uneyama C, Hirose M, Mitsumori K. Testicular toxicity of nitrofurazone causing germ cell apoptosis in rats. Arch Toxicol. 2001 Jul;75(5):297-305. doi: 10.1007/s002040100231. PMID: 11548123.

1: Pogoda D, Janczak J, Videnova-Adrabinska V. New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr 1;72(Pt 2):263-73. doi: 10.1107/S2052520615024956. Epub 2016 Apr 1. PubMed PMID: 27048728. 2: Guo X, Wang Y, Wu F, Ni Y, Kokot S. The use of tungsten disulfide dots as highly selective, fluorescent probes for analysis of nitrofurazone. Talanta. 2015 Nov 1;144:1036-43. doi: 10.1016/j.talanta.2015.07.055. Epub 2015 Jul 19. PubMed PMID: 26452924. 3: Zhang S, Guo Y, Yan Z, Sun X, Zhang X. A selective biomarker for confirming nitrofurazone residues in crab and shrimp using ultra-performance liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2015 Dec;407(30):8971-7. doi: 10.1007/s00216-015-9058-7. Epub 2015 Oct 1. PubMed PMID: 26427505. 4: Yasojima EY, Ribeiro Júnior RF, Pessôa TC, Cavalcante LC, Ramos SR, Serruya YA, de Moraes MM. Effects of nitrofurazone on correction of abdominal wall defect treated with polypropylene mesh involved by fibrous tissue. Acta Cir Bras. 2015 Oct;30(10):686-90. doi: 10.1590/S0102-865020150100000006. Erratum in: Acta Cir Bras. 2015 Dec;30(12):858. PubMed PMID: 26560427. 5: Hong Y, Liu S, Lin X, Li J, Yi Z, Al-Rasheid KA. Recognizing the importance of exposure-dose-response dynamics for ecotoxicity assessment: nitrofurazone-induced antioxidase activity and mRNA expression in model protozoan Euplotes vannus. Environ Sci Pollut Res Int. 2015 Jun;22(12):9544-53. doi: 10.1007/s11356-015-4096-4. Epub 2015 Jan 29. PubMed PMID: 25628113. 6: Stadler RH, Verzegnassi L, Seefelder W, Racault L. Why semicarbazide (SEM) is not an appropriate marker for the usage of nitrofurazone on agricultural animals. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(11):1842-50. doi: 10.1080/19440049.2015.1086028. Epub 2015 Oct 6. PubMed PMID: 26359628. 7: Kottur J, Sharma A, Gore KR, Narayanan N, Samanta B, Pradeepkumar PI, Nair DT. Unique structural features in DNA polymerase IV enable efficient bypass of the N2 adduct induced by the nitrofurazone antibiotic. Structure. 2015 Jan 6;23(1):56-67. doi: 10.1016/j.str.2014.10.019. Epub 2014 Dec 11. PubMed PMID: 25497730. 8: Li J, Zhou L, Lin X, Yi Z, Al-Rasheid KA. Characterizing dose-responses of catalase to nitrofurazone exposure in model ciliated protozoan Euplotes vannus for ecotoxicity assessment: enzyme activity and mRNA expression. Ecotoxicol Environ Saf. 2014 Feb;100:294-302. doi: 10.1016/j.ecoenv.2013.08.021. Epub 2013 Sep 26. PubMed PMID: 24075098. 9: Vila MM, Coelho SL, Chaud MV, Tubino M, Oliveira JM Jr, Balcao VM. Development and characterization of a hydrogel containing nitrofurazone for antimicrobial topical applications. Curr Pharm Biotechnol. 2014;15(2):182-90. PubMed PMID: 25135342. 10: Prieto J. Whether nitrofurazone-impregnated catheters have a clinically important impact on the risk of UTI compared to standard catheters is uncertain, but they may be cost-effective for the NHS. Evid Based Nurs. 2014 Jan;17(1):28-9. doi: 10.1136/eb-2013-101283. Epub 2013 May 21. PubMed PMID: 23696230. 11: Kouchak M, Ameri A, Naseri B, Kargar Boldaji S. Chitosan and polyvinyl alcohol composite films containing nitrofurazone: preparation and evaluation. Iran J Basic Med Sci. 2014 Jan;17(1):14-20. PubMed PMID: 24592302; PubMed Central PMCID: PMC3938881. 12: Balcao VM, Santos MG, Martins PR, Chaud MV, Oliveira Junior JM, Tubino M, Vila MM. Development and characterization of a gel formulation integrating microencapsulated nitrofurazone. Curr Pharm Biotechnol. 2014;14(12):1036-47. PubMed PMID: 24433503. 13: Barati F, Javanbakht J, Adib-Hashemi F, Hosseini E, Safaeie R, Rajabian M, Razmjoo M, Sedaghat R, Aghamohammad Hassan M. Histopathological and clinical evaluation of Kombucha tea and Nitrofurazone on cutaneous full-thickness wounds healing in rats: an experimental study. Diagn Pathol. 2013 Jul 17;8:120. doi: 10.1186/1746-1596-8-120. PubMed PMID: 23866960; PubMed Central PMCID: PMC3846920. 14: Nogueira Filho MA, Padilha EC, Campos ML, Pontes Machado DV, Davanço MG, Pestana KC, Chin CM, Peccinini RG. Pharmacokinetics of hydroxymethylnitrofurazone and its parent drug nitrofurazone in rabbits. Drug Metab Lett. 2013 Mar;7(1):58-64. PubMed PMID: 23957951. 15: Erdos Z, Pearson K, Goedken M, Menzel K, Sistare FD, Glaab WE, Saldutti LP. Inhibin B response to testicular toxicants hexachlorophene, ethane dimethane sulfonate, di-(n-butyl)-phthalate, nitrofurazone, DL-ethionine, 17-alpha ethinylestradiol, 2,5-hexanedione, or carbendazim following short-term dosing in male rats. Birth Defects Res B Dev Reprod Toxicol. 2013 Feb;98(1):41-53. doi: 10.1002/bdrb.21035. Epub 2013 Jan 24. PubMed PMID: 23348767. 16: Ni Y, Wang P, Kokot S. Voltammetric investigation of DNA damage induced by nitrofurazone and short-lived nitro-radicals with the use of an electrochemical DNA biosensor. Biosens Bioelectron. 2012 Oct-Dec;38(1):245-51. doi: 10.1016/j.bios.2012.05.034. Epub 2012 Jun 6. PubMed PMID: 22717476. 17: Johnson JR, Johnston B, Kuskowski MA. In vitro comparison of nitrofurazone- and silver alloy-coated foley catheters for contact-dependent and diffusible inhibition of urinary tract infection-associated microorganisms. Antimicrob Agents Chemother. 2012 Sep;56(9):4969-72. doi: 10.1128/AAC.00733-12. Epub 2012 Jul 2. PubMed PMID: 22751541; PubMed Central PMCID: PMC3421844. 18: Deng F, Dong C, Liu Y. Characterization of the interaction between nitrofurazone and human serum albumin by spectroscopic and molecular modeling methods. Mol Biosyst. 2012 Apr;8(5):1446-51. doi: 10.1039/c2mb05467a. Epub 2012 Feb 15. PubMed PMID: 22337082. 19: Zhou L, Li J, Lin X, Al-Rasheid KA. Use of RAPD to detect DNA damage induced by nitrofurazone in marine ciliate, Euplotes vannus (Protozoa, Ciliophora). Aquat Toxicol. 2011 Jun;103(3-4):225-32. doi: 10.1016/j.aquatox.2011.03.002. Epub 2011 Mar 15. PubMed PMID: 21481819. 20: Becerro de Bengoa Vallejo R, Losa Iglesias ME, Cervera LA, Fernández DS, Prieto JP. Efficacy of intraoperative surgical irrigation with polihexanide and nitrofurazone in reducing bacterial load after nail removal surgery. J Am Acad Dermatol. 2011 Feb;64(2):328-35. doi: 10.1016/j.jaad.2010.01.011. Epub 2010 Nov 26. PubMed PMID: 21112671.