Metronidazole | CAS#443-48-1 | CAS#13182-89-3 | Antibiotic | Antiprotozoal

MedKoo Cat#: 318262 | Name: Metronidazole

Description:

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

Metronidazole is an antibiotic and antiprotozoal medication. It is used either alone or with other antibiotics to treat pelvic inflammatory disease, endocarditis, and bacterial vaginosis. It is effective for dracunculiasis, giardiasis, trichomoniasis, and amebiasis. It is the drug of choice for a first episode of mild-to-moderate Clostridium difficile colitis.

Chemical Structure

Metronidazole

CAS#443-48-1 (free base)

Theoretical Analysis

MedKoo Cat#: 318262

Name: Metronidazole

CAS#: 443-48-1 (free base)

Chemical Formula: C6H9N3O3

Exact Mass: 171.0644

Molecular Weight: 171.15

Elemental Analysis: C, 42.10; H, 5.30; N, 24.55; O, 28.04

Price and Availability

Size	Price	Availability
1g	USD 90.00	Ready to ship
2g	USD 150.00	Ready to ship
5g	USD 250.00	Ready to ship
10g	USD 350.00	Ready to ship
25g	USD 450.00	Ready to ship

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Related CAS #

443-48-1 (free base) 69198-10-3 (HCl) 1460293-84-8 (sodium)

Synonym

Metronidazole, Flagyl, Metro, Trichopol, Vagilen

IUPAC/Chemical Name

2-(2-methyl-5-nitroimidazol-1-yl)ethanol

InChi Key

VAOCPAMSLUNLGC-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

SMILES Code

O=[N+](C1=CN=C(C)N1CCO)[O-]

Appearance

White to light yellow crystalline 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

Certificate of Analysis

View CoA: current batch, Lot#C21B09B11

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DNA229; Binding Agent994; Trichomoniasis; Acute intestinal amebiasis; Anaerobic bacterial infections

In vitro activity:

The aim of this study was to evaluate the in vitro susceptibility of six bovine isolates of Tritrichomonas foetus to Mz in aerobic (AC) and anaerobic (ANC) conditions by means of the calculation of the 50% inhibitory concentration (IC50), by flow cytometry, and also to analyze minimum lethal concentration (MLC) by means of recovery tests post-treatment in vitro. IC50 values ranged from 1.06 to 1.25 μM in ANC and from 1.44 to 3.03 μM in AC, these being the only ones reported at 48 h for these protozoa. With respect to MLC at 48 h, the results were from 3.67 to 7.35 μM in ANC, and from 7.35 to 14.7 μM for AC, where two isolates (Tf0 and Tf2) for AC and one (Tf2) for ANC showed higher values than those described in the literature. Flow cytometry has proven to be an effective, rapid and objective methodology and very useful in susceptibility tests. The data obtained through these tests allow us to describe the susceptibility exhibited by these protozoa, this being valuable information when establishing dosages in Mz treatments. Reference: Rivero MB, Luque ME, Abdala ME, Luna BE, Di Lullo D, Carranza PG, Rivero FD. Flow cytometry evaluation of in vitro susceptibility of bovine isolates of Tritrichomonas foetus to metronidazole. Vet Parasitol. 2019 Mar;267:84-89. doi: 10.1016/j.vetpar.2019.02.004. Epub 2019 Feb 16. PMID: 30878091.

In vivo activity:

Results from an antimicrobial assay indicated that metronidazole at a concentration of 0.5 μg/mL successfully eliminated in vitro protozoal growth of bovine Tritrichomonas foetus. The estimated effective intravenous dose was two treatments with 60 mg/kg metronidazole, 24 h apart. A bull that had tested positive for Tritrichomonas foetus culture at weekly intervals for 5 weeks prior to treatment was negative for Tritrichomonas foetus culture at weekly intervals for five consecutive weeks following this treatment regimen. An objective evaluation of the published evidence on the potential public health significance of using metronidazole to treat Tritrichomonas foetus in bulls provides encouragement for veterinarians and regulators to consider approaches that might lead to permitting the legal use of metronidazole in bulls. The study demonstrated successful inhibition of Tritrichomonas foetus both in vitro and in vivo with metronidazole. The current status of metronidazole is that the Animal Medicinal Drug Use Clarification Act of 1994 prohibits its extra-label use in food-producing animals. Veterinarians and regulators should consider approaches that might lead to permitting the legal use of metronidazole in bulls. Reference: Love D, Fajt VR, Hairgrove T, Jones M, Thompson JA. Metronidazole for the treatment of Tritrichomonas foetus in bulls. BMC Vet Res. 2017 Apr 14;13(1):107. doi: 10.1186/s12917-017-0999-2. PMID: 28410582; PMCID: PMC5391598.

	Solvent	mg/mL	mM
Solubility
	Water	10.0	58.43
	Ethanol	5.0	29.21
	Methanol	0.0	2.92
	Chloroform	0.0	2.92
	DMSO	34.0	198.25

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 171.15 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:

Rivero MB, Luque ME, Abdala ME, Luna BE, Di Lullo D, Carranza PG, Rivero FD. Flow cytometry evaluation of in vitro susceptibility of bovine isolates of Tritrichomonas foetus to metronidazole. Vet Parasitol. 2019 Mar;267:84-89. doi: 10.1016/j.vetpar.2019.02.004. Epub 2019 Feb 16. PMID: 30878091.

In vitro protocol:

In vivo protocol:

Love D, Fajt VR, Hairgrove T, Jones M, Thompson JA. Metronidazole for the treatment of Tritrichomonas foetus in bulls. BMC Vet Res. 2017 Apr 14;13(1):107. doi: 10.1186/s12917-017-0999-2. PMID: 28410582; PMCID: PMC5391598.

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J Antimicrob Chemother. 2014 Nov;69(11):2892-900. doi: 10.1093/jac/dku261. Epub 2014 Jul 28. Review. PubMed PMID: 25074856. 5: Fjeld H, Raknes G. [Is combining metronidazole and alcohol really hazardous?]. Tidsskr Nor Laegeforen. 2014 Sep 16;134(17):1661-3. doi: 10.4045/tidsskr.14.0081. eCollection 2014 Sep 16. Review. Norwegian. PubMed PMID: 25223673. 6: Miljkovic V, Arsic B, Bojanic Z, Nikolic G, Nikolic Lj, Kalicanin B, Savic V. Interactions of metronidazole with other medicines: a brief review. Pharmazie. 2014 Aug;69(8):571-7. Review. PubMed PMID: 25158566. 7: Sgolastra F, Severino M, Petrucci A, Gatto R, Monaco A. Effectiveness of metronidazole as an adjunct to scaling and root planing in the treatment of chronic periodontitis: a systematic review and meta-analysis. J Periodontal Res. 2014 Feb;49(1):10-9. doi: 10.1111/jre.12089. Epub 2013 May 14. Review. PubMed PMID: 23668676. 8: Cantador AA, Meschia JF, Freeman WD, Tatum WO. Nonconvulsive status with metronidazole. Neurohospitalist. 2013 Oct;3(4):185-9. doi: 10.1177/1941874412470667. Review. PubMed PMID: 24198899; PubMed Central PMCID: PMC3810826. 9: Kafadar I, Moustafa F, Yalçın K, Klç BA. A rare adverse effect of metronidazole: nervous system symptoms. Pediatr Emerg Care. 2013 Jun;29(6):751-2. doi: 10.1097/PEC.0b013e318294f389. Review. PubMed PMID: 23736071. 10: Zandbergen D, Slot DE, Cobb CM, Van der Weijden FA. The clinical effect of scaling and root planing and the concomitant administration of systemic amoxicillin and metronidazole: a systematic review. J Periodontol. 2013 Mar;84(3):332-51. doi: 10.1902/jop.2012.120040. Epub 2012 May 21. Review. PubMed PMID: 22612369. 11: Sgolastra F, Gatto R, Petrucci A, Monaco A. Effectiveness of systemic amoxicillin/metronidazole as adjunctive therapy to scaling and root planing in the treatment of chronic periodontitis: a systematic review and meta-analysis. J Periodontol. 2012 Oct;83(10):1257-69. Epub 2012 Feb 14. Review. PubMed PMID: 22220767. 12: Vardakas KZ, Polyzos KA, Patouni K, Rafailidis PI, Samonis G, Falagas ME. Treatment failure and recurrence of Clostridium difficile infection following treatment with vancomycin or metronidazole: a systematic review of the evidence. Int J Antimicrob Agents. 2012 Jul;40(1):1-8. doi: 10.1016/j.ijantimicag.2012.01.004. Epub 2012 Mar 6. Review. PubMed PMID: 22398198. 13: Huang YT, Chen LA, Cheng SJ. Metronidazole-induced Encephalopathy: Case Report and Review Literature. Acta Neurol Taiwan. 2012 Jun;21(2):74-8. Review. PubMed PMID: 22879116. 14: Sgolastra F, Petrucci A, Gatto R, Monaco A. Effectiveness of systemic amoxicillin/metronidazole as an adjunctive therapy to full-mouth scaling and root planing in the treatment of aggressive periodontitis: a systematic review and meta-analysis. J Periodontol. 2012 Jun;83(6):731-43. doi: 10.1902/jop.2011.110432. Epub 2011 Nov 3. Review. PubMed PMID: 22050545. 15: Stover KR, Riche DM, Gandy CL, Henderson H. What would we do without metronidazole? Am J Med Sci. 2012 Apr;343(4):316-9. doi: 10.1097/MAJ.0b013e3182254bd6. Review. PubMed PMID: 21817887. 16: Kuriyama A, Jackson JL, Doi A, Kamiya T. Metronidazole-induced central nervous system toxicity: a systematic review. Clin Neuropharmacol. 2011 Nov-Dec;34(6):241-7. doi: 10.1097/WNF.0b013e3182334b35. Review. PubMed PMID: 21996645. 17: Shakir L, Javeed A, Ashraf M, Riaz A. Metronidazole and the immune system. Pharmazie. 2011 Jun;66(6):393-8. Review. PubMed PMID: 21699075. 18: Desai JA, Dobson J, Melanson M, Pari G, Jin AY. Metronidazole-induced encephalopathy: case report and review of MRI findings. Can J Neurol Sci. 2011 May;38(3):512-3. Review. PubMed PMID: 21515514. 19: Bottenberg MM, Hegge KA, Eastman DK, Kumar R. Metronidazole-induced encephalopathy: a case report and review of the literature. J Clin Pharmacol. 2011 Jan;51(1):112-6. doi: 10.1177/0091270010362905. Epub 2010 Mar 10. Review. PubMed PMID: 20220041. 20: Perras C, Tsakonas E, Ndegwa S, Conly J, Valiquette L, Farrah K. Vancomycin or Metronidazole for Treatment of Clostridium difficile Infection: Clinical and Economic Analyses [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2011 Jan. Available from http://www.ncbi.nlm.nih.gov/books/NBK174415/ PubMed PMID: 24354025.