Acromona;Anagiardil;Apo-Metronidazole;Arilin;Atrivyl;Bayer 5360;Bexon;Clont;Cont;Danizol;Deflamon;Deflamon-Wirkstoff;Efloran;Elyzol;Entizol;Eumin;Flagemona;Flagesol;Flagil;Flagyl;Flagyl ER;Flagyl I.V.;Flegyl;Fossyol;Giatricol;Gineflavir;Klion;Klont;Meronidal;Metric 21;Metro Cream;Metro I.V.;Metro I.V. In Plastic Container;Metrocream;Metrogel;Metrogel-Vaginal;Metrolag;Metrolotion;Metrolyl;Metromidol;Metronidaz;Metrotop;Mexibol;Monagyl;Monasin;Nalox;Neo-Tric;Nida;Nidagel;Noritate;Novonidazol;Orvagil;Protostat;Rathimed;Sanatrichom;Satric;Takimetol;Trichazol;Trichex;Tricho Cordes;Tricho-Gynaedron;Trichocide;Trichomol;Trichopal;Trichopol;Tricocet;Tricom;Tricowas B;Trikacide;Trikamon;Trikojol;Trikozol;Trimeks;Trivazol;Vagilen;Vagimid;Vertisal;Wagitran;Zadstat;

Methronidazole;Metronidazol;Metronidazole Benzoate;Metronidazole Hcl;Metronidazole in Plastic Container;Metronidazolo;

A nitroimidazole used to treat amebiasis; vaginitis; trichomonas infections; giardiasis; anaerobic bacteria; and treponemal infections. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).

• Abbott laboratories pharmaceutical products div
• Able laboratories inc
• Abraxis pharmaceutical products
• Alembic ltd
• Altana inc
• B braun medical inc
• Baxter healthcare corp
• Claris lifesciences ltd
• Elkins sinn div ah robins co inc
• G and w laboratories inc
• Galderma laboratories lp
• Gd searle llc
• Graceway pharmaceuticals llc
• Halsey drug co inc
• Hospira inc
• International medication systems ltd
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Laboratorios aplicaciones farmaceuticas sa de cv
• Lnk international inc
• Mutual pharmaceutical co inc
• Ortho mcneil pharmaceutical inc
• Par pharmaceutical inc
• Pliva inc
• Sandoz inc
• Sanofi aventis us llc
• Savage laboratories inc div altana inc
• Superpharm corp
• Taro pharmaceutical industries ltd
• Teva pharmaceuticals usa
• Teva pharmaceuticals usa inc
• Tolmar inc
• Watson laboratories inc
• World gen llc

Synthesis Reference

Not Available

General Reference

Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. Pubmed Lamont RF: Can antibiotics prevent preterm birth—the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. Pubmed Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. Pubmed

Form	Route	Strength
Capsule	Oral
Cream	Intravaginal
Cream	Topical
Gel	Intravaginal
Gel	Topical
Liquid	Intravenous
Lotion	Topical
Solution	Intravenous
Tablet	Oral
Tablet, extended release	Oral

Unit description	Cost	Unit
MetroLotion 0.75% Lotion 59ml Bottle	292.66 USD	bottle
MetroCream 0.75% Cream 45 gm Tube	281.09 USD	tube
Metrogel 1% Gel 60 gm Tube	200.93 USD	tube
Metrogel 1% Kit Box	200.93 USD	box
Metrogel 1% kit	193.2 USD	kit
Noritate 1% Cream 60 gm Tube	156.44 USD	tube
MetroNIDAZOLE 0.75% Lotion 59ml Bottle	89.86 USD	bottle
MetroNIDAZOLE 0.75% Cream 45 gm Tube	80.87 USD	tube
MetroNIDAZOLE 0.75% Gel 45 gm Tube	74.0 USD	tube
MetroNIDAZOLE 0.75% Gel 70 gm Tube	68.53 USD	tube
Flagyl ER 750 mg 24 Hour tablet	13.2 USD	tablet
Flagyl er 750 mg tablet	12.7 USD	tablet
MetroNIDAZOLE 750 mg 24 Hour tablet	8.07 USD	tablet
Flagyl 500 mg tablet	6.24 USD	tablet
Metrocream 0.75% cream	5.99 USD	g
Danazol 200 mg capsule	5.63 USD	capsule
Flagyl 375 mg capsule	5.45 USD	capsule
Metrolotion topical 0.75%	4.77 USD	ml
Metronidazole benz powder	4.74 USD	g
Flagyl 250 mg tablet	3.49 USD	tablet
Danazol 100 mg capsule	2.98 USD	capsule
Noritate 1% cream	2.51 USD	g
Danazol 50 mg capsule	1.99 USD	capsule
Metronidazole powder	1.65 USD	g
Metronidazole 0.75% cream	1.34 USD	g
Metronidazole vaginal 0.75% gl	0.94 USD	g
Metronidazole 500 mg tablet	0.72 USD	tablet
Metrogel 0.75 % Gel	0.69 USD	g
Metrogel 1 % Gel	0.63 USD	g
Noritate 1 % Cream	0.58 USD	g
Rosasol 1 % Cream	0.57 USD	g
Metrocream 0.75 % Cream	0.52 USD	g
Metrolotion 0.75 % Lotion	0.52 USD	g
Metrogel-vaginal 0.75% gel	0.51 USD	g
Vandazole vaginal 0.75% gel	0.48 USD	g
Metronidazole 250 mg tablet	0.44 USD	tablet
Flagyl 10 % Cream	0.25 USD	g
Apo-Metronidazole 250 mg Tablet	0.06 USD	tablet
Flagyl 5 mg/ml	0.03 USD	ml
Metro iv 500 mg/100 ml	0.03 USD	ml
Metronidazole 5 mg/ml	0.03 USD	ml
Metronidazole 500 mg/100 ml	0.03 USD	ml

Type	small molecule

Classes

Nitroimidazoles

Substructures

Nitroimidazoles Hydroxy Compounds Oxoazaniums Nitro compounds Alcohols and Polyols Imidazoles Heterocyclic compounds Aromatic compounds Imines Cyanamides

antibacterials 抗细菌;

Indication	For the treatment of anaerobic infections and mixed infections, surgical prophylaxis requiring anaerobic coverage, Clostridium difficile-associated diarrhea and colitis, Helicobacter pylori infection and duodenal ulcer disease, bacterial vaginosis, Giardia lamblia gastro-enteritis, amebiasis caused by Entamoeba histolytica, acne rosacea (topical treatment), and Trichomonas infections.
Pharmacodynamics	Metronidazole, a synthetic antibacterial and antiprotozoal agent of the nitroimidazole class, is used against protozoa such as Trichomonas vaginalis, amebiasis, and giardiasis. Metronidazole is extremely effective against anaerobic bacterial infections and is also used to treat Crohn's disease, antibiotic-associated diarrhea, and rosacea.
Mechanism of action	Metronidazole is a prodrug. Unionized metronidazole is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. This reduced metronidazole then covalently binds to DNA, disrupt its helical structure, inhibiting bacterial nucleic acid synthesis and resulting in bacterial cell death.
Absorption	Well absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation.
Volume of distribution	Not Available
Protein binding	Less than 20% bound to plasma proteins.
Metabolism	Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.
Route of elimination	Not Available
Half life	6-8 hours
Clearance	Not Available
Toxicity	LD50=500 mg/kg/day (orally in rat). Adverse effects include reversible peripheral neuropathy with prolonged therapy, CNS toxicity, disulfiram effect with alcohol, dark red-brown urine, metallic taste, nausea, epigastric distress, dizziness, vertigo and paresthesias associated with high doses, and neutropenia (reversible and mild).
Affected organisms	Bacteria and protozoa
Pathways	Not Available

Properties
State	solid
Melting point	160 oC
Experimental Properties	Property Value Source water solubility <0.1g/100mL PhysProp logP -0.1 PhysProp logS -1.26 [ADME Research, USCD] PhysProp
Predicted Properties	Property Value Source water solubility 5.92e+00 g/l ALOGPS logP -0.15 ALOGPS logP -0.46 ChemAxon Molconvert logS -1.46 ALOGPS pKa ChemAxon Molconvert hydrogen acceptor count 4 ChemAxon Molconvert hydrogen donor count 1 ChemAxon Molconvert polar surface area 83.87 ChemAxon Molconvert rotatable bond count 3 ChemAxon Molconvert refractivity 41.22 ChemAxon Molconvert polarizability 15.81 ChemAxon Molconvert

Drug	Interaction
Acenocoumarol	Metronidazole may increase the anticoagulant effect of acenocoumarol.
Amobarbital	The barbiturate, amobarbital, decreases the effect of metronidazole.
Amprenavir	Increased risk of side effects (oral solution)
Anisindione	Metronidazole may increase the anticoagulant effect of anisindione.
Aprobarbital	The barbiturate, aprobarbital, decreases the effect of metronidazole.
Busulfan	Metronidazole increases the effect/toxicity of busulfan
Butabarbital	The barbiturate, butabarbital, decreases the effect of metronidazole.
Butalbital	The barbiturate, butalbital, decreases the effect of metronidazole.
Butethal	The barbiturate, butethal, decreases the effect of metronidazole.
Carbamazepine	Metronidazole increases the effect of carbamazepine
Dicumarol	Metronidazole may increase the anticoagulant effect of dicumarol.
Dihydroquinidine barbiturate	The barbiturate, dihydroquinidine barbiturate, decreases the effect of metronidazole.
Disulfiram	Possible acute psychosis and confusion
Fluorouracil	Risk of 5-FU toxicity when associated with metronidazole
Heptabarbital	The barbiturate, heptabarbital, decreases the effect of metronidazole.
Hexobarbital	The barbiturate, hexobarbital, decreases the effect of metronidazole.
Lithium	Metronidazole increases the effect and toxicity of lithium
Methohexital	The barbiturate, methohexital, decreases the effect of metronidazole.
Methylphenobarbital	The barbiturate, methylphenobarbital, decreases the effect of metronidazole.
Pentobarbital	The barbiturate, pentobarbital, decreases the effect of metronidazole.
Phenobarbital	The barbiturate, phenobarbital, decreases the effect of metronidazole.
Primidone	The barbiturate, primidone, decreases the effect of metronidazole.
Quinidine barbiturate	The barbiturate, quinidine barbiturate, decreases the effect of metronidazole.
Secobarbital	The barbiturate, secobarbital, decreases the effect of metronidazole.
Tacrolimus	Metronidazole increases the levels/toxicity of tacrolimus
Talbutal	The barbiturate, talbutal, decreases the effect of metronidazole.
Tamsulosin	Metronidazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Metronidazole is initiated, discontinued, or dose changed.
Tolterodine	Metronidazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tramadol	Metronidazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Trazodone	The CYP3A4 inhibitor, Metronidazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Metronidazole is initiated, discontinued or dose changed.
Warfarin	Metronidazole may increase the serum concentration of warfarin by decreasing its metabolism. Consider alternate therapy or a dose reduction in warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if metronidazole is initiated, discontinued or dose changed.

• Avoid alcohol.
• Take with food to reduce irritation.