Synonym
Nitrofurantoin, Macrobid, Macrodantin, 5-Nitrofurantoin, Furadantine, Furadonine
IUPAC/Chemical Name
(E)-1-(((5-nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione
InChi Key
NXFQHRVNIOXGAQ-YCRREMRBSA-N
InChi Code
InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
SMILES Code
O=C(N1)CN(/N=C/C2=CC=C([N+]([O-])=O)O2)C1=O
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
Biological target:
Nitrofurantoin is a potent and orally active broad-spectrum beta-lactamase antimicrobial agent.
In vitro activity:
By plating bacterial cells on agar plates containing nitrofurantoin, spontaneous nitrofurantoin-resistant E. coli mutants were isolated. Furthermore, the bacterial growth rate in the presence of nitrofurantoin at therapeutic levels was greatly reduced even for nitrofurantoin-resistant mutants.
Reference: J Antimicrob Chemother. 2008 Sep;62(3):495-503. https://pubmed.ncbi.nlm.nih.gov/18544599/
In vivo activity:
In this study, the compound, (Z)-1-[(5-nitrofuran-2-yl)methyleneamino]-imidazolidine-2,4-dione (nitrofurantoin), showed anti-T. gondii effects in vitro and in vivo. In T. gondii-infected female ICR mice, the inhibition rate of T. gondii growth in the peritoneal cavity was 44.7% compared to the negative control group after 4-day treatment with 100 mg/kg of nitrofurantoin.
Reference: Korean J Parasitol. 2016 Apr;54(2):155-61. https://pubmed.ncbi.nlm.nih.gov/27180573/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
25.0 |
104.97 |
|
| DMSO |
57.3 |
240.74 |
|
| DMSO:PBS (pH 7.2) (1:2) |
0.5 |
2.10 |
|
| Ethanol |
15.0 |
62.98 |
|
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
238.16
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. Sandegren L, Lindqvist A, Kahlmeter G, Andersson DI. Nitrofurantoin resistance mechanism and fitness cost in Escherichia coli. J Antimicrob Chemother. 2008 Sep;62(3):495-503. doi: 10.1093/jac/dkn222. Epub 2008 Jun 10. PMID: 18544599.
2. Martin WJ 2nd. Nitrofurantoin: evidence for the oxidant injury of lung parenchymal cells. Am Rev Respir Dis. 1983 Apr;127(4):482-6. doi: 10.1164/arrd.1983.127.4.482. PMID: 6838054.
3. Suganuma K, N'Da DD, Watanabe KI, Tanaka Y, Mossaad E, Elata A, Inoue N, Kawazu SI. Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection. Pathogens. 2022 Mar 9;11(3):331. doi: 10.3390/pathogens11030331. PMID: 35335655; PMCID: PMC8956101.
4. Yeo SJ, Jin C, Kim S, Park H. In Vitro and in Vivo Effects of Nitrofurantoin on Experimental Toxoplasmosis. Korean J Parasitol. 2016 Apr;54(2):155-61. doi: 10.3347/kjp.2016.54.2.155. Epub 2016 Apr 30. PMID: 27180573; PMCID: PMC4870977.
In vitro protocol:
1. Sandegren L, Lindqvist A, Kahlmeter G, Andersson DI. Nitrofurantoin resistance mechanism and fitness cost in Escherichia coli. J Antimicrob Chemother. 2008 Sep;62(3):495-503. doi: 10.1093/jac/dkn222. Epub 2008 Jun 10. PMID: 18544599.
2. Martin WJ 2nd. Nitrofurantoin: evidence for the oxidant injury of lung parenchymal cells. Am Rev Respir Dis. 1983 Apr;127(4):482-6. doi: 10.1164/arrd.1983.127.4.482. PMID: 6838054.
In vivo protocol:
1. Suganuma K, N'Da DD, Watanabe KI, Tanaka Y, Mossaad E, Elata A, Inoue N, Kawazu SI. Therapeutic Efficacy of Orally Administered Nitrofurantoin against Animal African Trypanosomosis Caused by Trypanosoma congolense Infection. Pathogens. 2022 Mar 9;11(3):331. doi: 10.3390/pathogens11030331. PMID: 35335655; PMCID: PMC8956101.
2. Yeo SJ, Jin C, Kim S, Park H. In Vitro and in Vivo Effects of Nitrofurantoin on Experimental Toxoplasmosis. Korean J Parasitol. 2016 Apr;54(2):155-61. doi: 10.3347/kjp.2016.54.2.155. Epub 2016 Apr 30. PMID: 27180573; PMCID: PMC4870977.
1: Giske CG. Contemporary resistance trends and mechanisms for the old antibiotics colistin, temocillin, fosfomycin, mecillinam and nitrofurantoin. Clin Microbiol Infect. 2015 Oct;21(10):899-905. doi: 10.1016/j.cmi.2015.05.022. Epub 2015 May 28. Review. PubMed PMID: 26027916.
2: Huttner A, Verhaegh EM, Harbarth S, Muller AE, Theuretzbacher U, Mouton JW. Nitrofurantoin revisited: a systematic review and meta-analysis of controlled trials. J Antimicrob Chemother. 2015 Sep;70(9):2456-64. doi: 10.1093/jac/dkv147. Epub 2015 Jun 11. Review. PubMed PMID: 26066581.
3: Kabbara WK, Kordahi MC. Nitrofurantoin-induced pulmonary toxicity: A case report and review of the literature. J Infect Public Health. 2015 Jul-Aug;8(4):309-13. doi: 10.1016/j.jiph.2015.01.007. Epub 2015 Mar 5. Review. PubMed PMID: 25747822.
4: Goldberg O, Moretti M, Levy A, Koren G. Exposure to nitrofurantoin during early pregnancy and congenital malformations: a systematic review and meta-analysis. J Obstet Gynaecol Can. 2015 Feb;37(2):150-6. Review. PubMed PMID: 25767948.
5: Štuhec M. Auditory hallucinations associated with nitrofurantoin use: case report and review of the literature. Wien Klin Wochenschr. 2014 Sep;126(17-18):549-52. doi: 10.1007/s00508-014-0577-6. Epub 2014 Aug 15. Review. PubMed PMID: 25123143.
6: Stock I. [Nitrofurantoin--clinical relevance in uncomplicated urinary tract infections]. Med Monatsschr Pharm. 2014 Jul;37(7):242-8. Review. German. PubMed PMID: 25065160.
7: Munoz-Davila MJ. Role of Old Antibiotics in the Era of Antibiotic Resistance. Highlighted Nitrofurantoin for the Treatment of Lower Urinary Tract Infections. Antibiotics (Basel). 2014 Feb 10;3(1):39-48. doi: 10.3390/antibiotics3010039. Review. PubMed PMID: 27025732; PubMed Central PMCID: PMC4790343.
8: Sakaan SA, Twilla JD, Usery JB, Winton JC, Self TH. Nitrofurantoin-induced hepatotoxicity: a rare yet serious complication. South Med J. 2014 Feb;107(2):107-13. doi: 10.1097/SMJ.0000000000000059. Review. PubMed PMID: 24926677.
9: Oplinger M, Andrews CO. Nitrofurantoin contraindication in patients with a creatinine clearance below 60 mL/min: looking for the evidence. Ann Pharmacother. 2013 Jan;47(1):106-11. doi: 10.1345/aph.1R352. Epub 2013 Jan 22. Review. PubMed PMID: 23341159.
10: Sud B, Salvaggio M, Greenfield R, Bronze MS. Part XI. Trimethoprim-sulfamethoxazole, nitrofurantoin, chloramphenicol, metronidazole and tinidazole, rifaximin, and nitazoxanide. J Okla State Med Assoc. 2007 Jul;100(7):267-72. Review. Erratum in: J Okla State Med Assoc. 2007 Oct;100(10):405. Greenfield, Ronald A [corrected to Greenfield, Ronald]. PubMed PMID: 17896614.
11: Cunha BA. New uses for older antibiotics: nitrofurantoin, amikacin, colistin, polymyxin B, doxycycline, and minocycline revisited. Med Clin North Am. 2006 Nov;90(6):1089-107. Review. PubMed PMID: 17116438.
12: Karpman E, Kurzrock EA. Adverse reactions of nitrofurantoin, trimethoprim and sulfamethoxazole in children. J Urol. 2004 Aug;172(2):448-53. Review. PubMed PMID: 15247700.
13: Karmon Y, Edoute Y. [Hepatic injury associated with use of nitrofurantoin]. Harefuah. 1999 Mar 1;136(5):406-8. Review. Hebrew. PubMed PMID: 10914251.
14: Paiva LA, Wright PJ, Koff RS. Long-term hepatic memory for hypersensitivity to nitrofurantoin. Am J Gastroenterol. 1992 Jul;87(7):891-3. Review. PubMed PMID: 1615946.
15: Gait JE. Hemolytic reactions to nitrofurantoin in patients with glucose-6-phosphate dehydrogenase deficiency: theory and practice. DICP. 1990 Dec;24(12):1210-3. Review. PubMed PMID: 2089833.
16: Coraggio MJ, Gross TP, Roscelli JD. Nitrofurantoin toxicity in children. Pediatr Infect Dis J. 1989 Mar;8(3):163-6. Review. PubMed PMID: 2652087.
17: Hof H. [Antimicrobial therapy with nitroheterocyclic compounds, for example, metronidazole and nitrofurantoin]. Immun Infekt. 1988 Dec;16(6):220-5. Review. German. PubMed PMID: 3061931.
18: D'Arcy PF. Nitrofurantoin. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):540-7. Review. PubMed PMID: 3896715.
19: Hainer BL, White AA. Nitrofurantoin pulmonary toxicity. J Fam Pract. 1981 Nov;13(6):817-23. Review. PubMed PMID: 7031172.
20: Conklin JD. The pharmacokinetics of nitrofurantoin and its related bioavailability. Antibiot Chemother (1971). 1978;25:233-52. Review. PubMed PMID: 352255.
