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Identification
NameMetronidazole
Accession NumberDB00916  (APRD00631)
TypeSmall Molecule
GroupsApproved
Description

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).

Structure
Thumb
Synonyms
1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole
1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole
1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrrole
1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole
1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole
1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole
1-(β-hydroxyethyl)-2-methyl-5-nitroimidazole
1-(β-oxyethyl)-2-methyl-5-nitroimidazole
2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole
2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole
2-methyl-5-nitroimidazole-1-ethanol
Metronidazol
Metronidazolum
External Identifiers
  • Bayer 5360
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flagyltablet, film coated500 mg/1oralG.D. Searle LLC Division of Pfizer Inc1963-07-18Not applicableUs
Flagylcapsule500 mgoralSanofi Aventis Canada Inc1979-12-31Not applicableCanada
Flagylcapsule375 mg/1oralG.D. Searle LLC Division of Pfizer Inc1995-05-03Not applicableUs
Flagyltablet, film coated250 mg/1oralG.D. Searle LLC Division of Pfizer Inc1963-07-18Not applicableUs
Flagyl 500 500mgsuppository500 mgvaginalAventis Pharma Inc1960-12-312003-07-22Canada
Flagyl Cream 10%cream10 %vaginalSanofi Aventis Canada Inc1970-12-31Not applicableCanada
Florazole ERtablet (extended-release)750 mgoralFerring Inc2002-10-102012-09-30Canada
Metrocreamcream7.5 mg/gtopicalGalderma Laboratories, L.P.1995-09-20Not applicableUs
Metrocream - Crm 0.75%cream.75 %topicalGalderma Canada Inc1996-12-02Not applicableCanada
Metrogelgel10 mg/gtopicalPhysicians Total Care, Inc.2006-07-28Not applicableUs
Metrogelgel10 mg/gtopicalGalderma Laboratories, L.P.2005-06-30Not applicableUs
Metrogelgel7.5 mg/gvaginalPhysicians Total Care, Inc.1994-12-19Not applicableUs
Metrogel 0.75%gel0.75 %topicalGalderma Canada Inc1994-12-31Not applicableCanada
Metrogel 1%gel1 %topicalGalderma Canada Inc2007-12-20Not applicableCanada
Metrogel-vaginalgel7.5 mg/gvaginalMedicis Pharmaceutical Corp2011-11-28Not applicableUs
Metrolotionlotion7.5 mg/mLtopicalGalderma Laboratories, L.P.1998-11-24Not applicableUs
Metrolotionlotion0.75 %topicalGalderma Canada Inc2004-03-26Not applicableCanada
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2012-07-10Not applicableUs
Metronidazolegel7.5 mg/gvaginalPhysicians Total Care, Inc.2012-06-04Not applicableUs
Metronidazoletablet500 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-16Not applicableUs
Metronidazolecream7.5 mg/gtopicalOwen Laboratories2009-06-18Not applicableUs
Metronidazolegel7.5 mg/gvaginalAidarex Pharmaceuticals LLC2007-03-31Not applicableUs
Metronidazolegel7.5 mg/gvaginalPreferred Pharmaceuticals, Inc.2012-02-14Not applicableUs
Metronidazoletablet500 mg/1oralApace Packaging2009-12-06Not applicableUs
Metronidazolegel7.5 mg/gvaginalOceanside Pharmaceuticals2015-04-01Not applicableUs
Metronidazolecapsule500 mgoralAa Pharma Inc2003-11-27Not applicableCanada
Metronidazolelotion7.5 mg/mLtopicalActavis Mid Atlantic LLC,2009-05-282016-02-25Us
Metronidazolesolution500 mg/100mLintravenousB. Braun Medical Inc.1983-09-29Not applicableUs
Metronidazolelotion7.5 mg/gtopicalPrasco Laboratories2009-05-28Not applicableUs
Metronidazoletablet500 mg/1oralPhysicians Total Care, Inc.1995-04-24Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousHospira, Inc.1983-11-18Not applicableUs
Metronidazolecream7.5 mg/gtopicalPrasco Laboratories2009-06-18Not applicableUs
Metronidazoletablet250 mg/1oralPhysicians Total Care, Inc.1996-10-17Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousBaxter Healthcare Corporation1981-12-24Not applicableUs
Metronidazolegel7.5 mg/gvaginalPrasco Laboratories2007-03-31Not applicableUs
Metronidazoletablet250 mgoralAa Pharma Inc1982-12-31Not applicableCanada
Metronidazoleinjection, solution500 mg/100mLintravenousBaxter Healthcare Corporation1981-12-24Not applicableUs
Metronidazolesolution500 mg/100mLintravenousCardinal Health1983-09-29Not applicableUs
Metronidazolegel10 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-06-30Not applicableUs
Metronidazole 5 mg/ml Injectionliquid5 mgintravenousBaxter Corporation1990-12-31Not applicableCanada
Metronidazole Injection USPsolution5 mgintravenousHospira Healthcare Corporation1987-12-31Not applicableCanada
Metronidazole Tab 250mgtablet250 mgoralPro Doc Limitee1978-12-312012-07-23Canada
Metronidazole Topical Cream, 0.75%cream7.5 mg/gtopicalActavis Mid Atlantic LLC, Lincolnton, NC 280922009-06-18Not applicableUs
Metronidazole Topical Gelgel7.5 mg/gtopicalOwen Laboratories2014-03-01Not applicableUs
Metronidazole Topical Gelgel7.5 mg/gtopicalPrasco Laboratories2014-03-01Not applicableUs
Nidagel Vaginal Gel 0.75%gel0.75 %vaginalValeant Canada Lp Valeant Canada S.E.C.1994-12-31Not applicableCanada
Noritatecream1 %topicalValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Noritatecream10 mg/gtopicalPhysicians Total Care, Inc.2005-09-29Not applicableUs
Noritatecream10 mg/60gtopicalValeant Pharmaceuticals North America LLC2013-08-09Not applicableUs
Novo-nidazol Tab 250mgtablet250 mgoralNovopharm Limited1971-12-31Not applicableCanada
Nuvessagel65 mg/5gvaginalActavis Pharma, Inc.2015-01-01Not applicableUs
PMS-metronidazolecapsule500 mgoralPharmascience Inc1989-12-31Not applicableCanada
PMS-metronidazole 250mg/tabtablet250 mgoralPharmascience Inc1984-12-31Not applicableCanada
Vandazolegel7.5 mg/gvaginalUpsher Smith Laboratories, Inc.2005-10-04Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-metronidazoletablet250 mgoralApotex IncNot applicableNot applicableCanada
Apo-metronidazolecapsule500 mgoralApotex IncNot applicableNot applicableCanada
Metronidazoletablet250 mg/1oralPreferred Pharmaceuticals Inc.2015-10-08Not applicableUs
Metronidazoletablet500 mg/1oralNorthwind Pharmaceuticals2015-01-15Not applicableUs
Metronidazoletablet500 mg/1oralAurobindo Pharma Limited2015-05-29Not applicableUs
Metronidazoletablet250 mg/1oralPliva Inc.1990-09-30Not applicableUs
Metronidazoletablet500 mg/1oralRising Pharmaceuticals, Inc.2016-02-22Not applicableUs
Metronidazoletablet500 mg/1oralDIRECT RX2015-01-01Not applicableUs
Metronidazoletablet250 mg/1oralPreferred Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazoletablet250 mg/1oralDepartment Of State Health Services, Pharmacy Branch1990-09-30Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2012-08-22Not applicableUs
Metronidazoletablet500 mg/1oralSTAT Rx USA LLC1990-09-30Not applicableUs
Metronidazolegel7.5 mg/gvaginalSandoz Inc.2006-10-31Not applicableUs
Metronidazolegel7.5 mg/gtopicalG & W LABORATORIES, INC.2011-04-01Not applicableUs
Metronidazoletablet500 mg/1oralLiberty Pharmaceuticals, Inc.1990-09-30Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousPfizer Labs, Division of Pfizer Inc2008-11-20Not applicableUs
Metronidazoletablet500 mg/1oralMylan Institutional Inc.2015-04-29Not applicableUs
Metronidazoletablet500 mg/1oralCardinal Health2012-10-11Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2012-09-102016-03-11Us
Metronidazoletablet250 mg/1oralA S Medication Solutions Llc1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralDIRECT RX2014-01-01Not applicableUs
Metronidazolegel7.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2006-07-18Not applicableUs
Metronidazoletablet500 mg/1oralClinical Solutions Wholesale, Llc1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralCardinal Health2011-10-06Not applicableUs
Metronidazoletablet250 mg/1oralCarilion Materials Management1990-09-30Not applicableUs
Metronidazoletablet500 mg/1oralNorthwind Pharmaceuticals, LLC2014-09-17Not applicableUs
Metronidazoletablet250 mg/1oralAurobindo Pharma Limited2015-05-29Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2012-09-11Not applicableUs
Metronidazoletablet250 mg/1oralRising Pharmaceuticals, Inc.2016-02-22Not applicableUs
Metronidazoletablet500 mg/1oralAmerican Health Packaging2014-01-202015-12-31Us
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2011-12-15Not applicableUs
Metronidazoletablet, film coated500 mg/1oralApotheca Inc.2014-06-01Not applicableUs
Metronidazolecream7.5 mg/gtopicalG&W Laboratories, Inc.2008-03-13Not applicableUs
Metronidazoletablet250 mg/1oralLiberty Pharmaceuticals, Inc.1990-09-30Not applicableUs
Metronidazolegel7.5 mg/gtopicalRebel Distributors Corp2006-07-13Not applicableUs
Metronidazoletablet250 mg/1oralCardinal Health2012-10-11Not applicableUs
Metronidazoletablet500 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Metronidazoletablet500 mg/1oralDIRECT RX2014-01-01Not applicableUs
Metronidazoletablet500 mg/1oralSun Pharmaceutical Industries, Inc.1986-07-16Not applicableUs
Metronidazoletablet500 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Metronidazoletablet250 mg/1oralNorthwind Pharmaceuticals2014-12-16Not applicableUs
Metronidazoletablet250 mg/1oralReady Meds1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2011-05-03Not applicableUs
Metronidazoletablet500 mg/1oralCardinal Health2015-04-29Not applicableUs
Metronidazoletablet500 mg/1oralBlue Point Laboratories2014-03-132015-12-31Us
Metronidazolecapsule375 mg/1oralHeritage Pharmaceuticals Inc.2011-08-23Not applicableUs
Metronidazoletablet500 mg/1oralBlenheim Pharmacal, Inc.2015-07-27Not applicableUs
Metronidazoletablet500 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-09-01Not applicableUs
Metronidazoletablet500 mg/1oralKAISER FOUNDATION HOSPITALS2003-12-31Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousClaris Lifesciences Inc.2008-11-20Not applicableUs
Metronidazoletablet250 mg/1oralCardinal Health1998-08-08Not applicableUs
Metronidazoletablet250 mg/1oralH.J. Harkins Company, Inc.2011-10-07Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2014-12-23Not applicableUs
Metronidazoletablet250 mg/1oralSun Pharmaceutical Industries, Inc.1986-07-16Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2016-02-03Not applicableUs
Metronidazolegel7.5 mg/gtopicalObagi Medical Products, Inc.2006-07-132015-12-29Us
Metronidazoletablet500 mg/1oralHeritage Pharmaceuticals Inc.2013-12-16Not applicableUs
Metronidazoletablet250 mg/1oralBlenheim Pharmacal, Inc.2013-11-13Not applicableUs
Metronidazoletablet500 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1984-12-20Not applicableUs
Metronidazolelotion7.5 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2006-05-24Not applicableUs
Metronidazoletablet500 mg/1oralPd Rx Pharmaceuticals, Inc.2013-12-16Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousClaris Lifesciences Inc.2008-11-20Not applicableUs
Metronidazolegel7.5 mg/gtopicalPhysicians Total Care, Inc.2010-09-24Not applicableUs
Metronidazoletablet500 mg/1oralH.J. Harkins Company, Inc.2011-10-07Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2014-10-20Not applicableUs
Metronidazoletablet500 mg/1oralAppco Pharmaceuticals Corp2015-09-232016-03-22Us
Metronidazoletablet250 mg/1oralAmerican Health Packaging2014-01-20Not applicableUs
Metronidazoletablet500 mg/1oralMylan Institutional Inc.2012-08-20Not applicableUs
Metronidazoletablet500 mg/1oralReady Meds2011-08-22Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2011-04-13Not applicableUs
Metronidazoletablet250 mg/1oralHeritage Pharmaceuticals Inc.2013-12-16Not applicableUs
Metronidazoletablet500 mg/1oralBlenheim Pharmacal, Inc.2013-12-20Not applicableUs
Metronidazoletablet250 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1984-12-20Not applicableUs
Metronidazolecream7.5 mg/gtopicalE.FOUGERA & CO. A division of Fougera Pharmaceuticals Inc.2004-05-28Not applicableUs
Metronidazoletablet500 mg/1oralPd Rx Pharmaceuticals, Inc.2013-12-16Not applicableUs
Metronidazoletablet500 mg/1oralLake Erie Medical DBA Quality Care Products LLC2011-08-22Not applicableUs
Metronidazolelotion7.5 mg/mLtopicalPhysicians Total Care, Inc.2008-03-27Not applicableUs
Metronidazoletablet500 mg/1oralLucid Pharma Llc2015-05-29Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2014-09-15Not applicableUs
Metronidazoletablet250 mg/1oralAppco Pharmaceuticals Corp2015-09-232016-03-22Us
Metronidazoletablet500 mg/1oralBlue Point Laboratories2014-09-24Not applicableUs
Metronidazoletablet250 mg/1oralMylan Institutional Inc.2012-08-20Not applicableUs
Metronidazoletablet250 mg/1oralbryant ranch prepack2010-09-01Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2010-11-15Not applicableUs
Metronidazoletablet500 mg/1oralCronus Pharma LLC2015-05-29Not applicableUs
Metronidazoletablet250 mg/1oralPreferred Pharmaceuticals, Inc.2014-02-27Not applicableUs
Metronidazoletablet500 mg/1oralActavis Pharma, Inc.2014-11-24Not applicableUs
Metronidazolegel7.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2006-06-06Not applicableUs
Metronidazoletablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazoletablet500 mg/1oralAidarex Pharmaceuticals LLC2011-08-22Not applicableUs
Metronidazolecream7.5 mg/gtopicalPhysicians Total Care, Inc.2006-08-14Not applicableUs
Metronidazoletablet250 mg/1oralLucid Pharma Llc2015-05-29Not applicableUs
Metronidazoletablet500 mg/1oralSt Marys Medical Park Pharmacy2013-01-10Not applicableUs
Metronidazoletablet500 mg/1oralPd Rx Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazoletablet250 mg/1oralBlue Point Laboratories2014-03-13Not applicableUs
Metronidazoletablet500 mg/1oralUnit Dose Services2011-08-22Not applicableUs
Metronidazoletablet500 mg/1oralbryant ranch prepack2010-09-01Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2010-11-04Not applicableUs
Metronidazoletablet250 mg/1oralCronus Pharma LLC2015-05-29Not applicableUs
Metronidazoletablet500 mg/1oralPreferred Pharmaceuticals, Inc.2013-12-16Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2014-12-05Not applicableUs
Metronidazoletablet500 mg/1oralRebel Distributors Corp2010-09-01Not applicableUs
Metronidazoletablet500 mg/1oralBlenheim Pharmacal, Inc.2010-04-14Not applicableUs
Metronidazoletablet500 mg/1oralA S Medication Solutions Llc2011-08-22Not applicableUs
Metronidazolegel7.5 mg/gvaginalREMEDYREPACK INC.2014-02-28Not applicableUs
Metronidazoletablet500 mg/1oralClinical Solutions Wholesale2011-08-22Not applicableUs
Metronidazoletablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazolecream7.5 mg/gtopicalHarris Pharmaceutical, Inc.2008-03-13Not applicableUs
Metronidazoletablet250 mg/1oralUnit Dose Services2011-08-22Not applicableUs
Metronidazoletablet250 mg/1oralProficient Rx LP1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2010-10-10Not applicableUs
Metronidazoletablet250 mg/1oralCentral Texas Community Health Centers1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralPreferred Pharmaceuticals, Inc.2014-10-07Not applicableUs
Metronidazoletablet250 mg/1oralRebel Distributors Corp2010-09-01Not applicableUs
Metronidazoletablet250 mg/1oralMajor Pharmaceuticals1998-08-08Not applicableUs
Metronidazoletablet500 mg/1oralActavis Pharma, Inc.2011-08-22Not applicableUs
Metronidazoleinjection, solution500 mg/100mLintravenousWest ward Pharmaceutical Corp2009-08-04Not applicableUs
Metronidazoletablet500 mg/1oralPd Rx Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazoletablet, film coated500 mg/1oralUnichem Pharmaceuticals (USA), Inc.2014-06-01Not applicableUs
Metronidazoletablet500 mg/1oralMed Vantx, Inc.1990-09-30Not applicableUs
Metronidazoletablet500 mg/1oralPliva Inc.1990-09-30Not applicableUs
Metronidazoletablet500 mg/1oralProficient Rx LP1990-09-30Not applicableUs
Metronidazoletablet250 mg/1oralREMEDYREPACK INC.2010-11-04Not applicableUs
Metronidazoletablet500 mg/1oralPreferred Pharmaceuticals, Inc.2010-09-01Not applicableUs
Metronidazoletablet250 mg/1oralSTAT Rx USA LLC1990-09-30Not applicableUs
Metronidazolegel10 mg/gtopicalSandoz Inc.2013-07-01Not applicableUs
Metronidazoletablet250 mg/1oralActavis Pharma, Inc.2011-08-22Not applicableUs
Metronidazolegel7.5 mg/gtopicalImpax Generics2006-07-13Not applicableUs
Metronidazolegel7.5 mg/gtopicalPruGen, Inc.2006-07-18Not applicableUs
Metronidazoletablet, film coated250 mg/1oralUnichem Pharmaceuticals (USA), Inc.2014-06-01Not applicableUs
Metronidazoletablet500 mg/1oralA S Medication Solutions Llc2011-08-22Not applicableUs
Metronidazoletablet500 mg/1oralREMEDYREPACK INC.2013-11-22Not applicableUs
Metronidazoletablet250 mg/1oralClinical Solutions Wholesale2011-08-22Not applicableUs
Metronidazoletablet500 mg/1oralCardinal Health2011-10-06Not applicableUs
Metronidazole 250 mgtablet, film coated250 mg/1oralVivimed Labs Limited2016-03-24Not applicableUs
Metronidazole 500 mgtablet, film coated500 mg/1oralVivimed Labs Limited2016-03-24Not applicableUs
RosadankitMedimetriks Pharmaceuticals, Inc.2011-08-01Not applicableUs
Rosadangel7.5 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2012-04-15Not applicableUs
Rosadancream7.5 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2011-08-30Not applicableUs
Rosadancream7.5 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2011-08-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Rosaclear SystemkitOMP, INC.2012-12-29Not applicableUs
International Brands
NameCompany
AcromonaNot Available
AnabactCambridge Healthcare Supplies
ArilinNot Available
ClontNot Available
DeflamonNot Available
EfloranNot Available
ElyzolNot Available
EntizolNot Available
FossyolNot Available
KlionNot Available
KlontNot Available
MetrolylNot Available
MetrotopNot Available
NaloxNot Available
NidagelNot Available
NovonidazolNot Available
OrvagilNot Available
ProtostatNot Available
TakimetolNot Available
TrichazoleNot Available
TrichexNot Available
TrichopolNot Available
Tricowas BNot Available
TrikacideNot Available
TrikozolNot Available
VagilenNot Available
VagimidNot Available
VertisalNot Available
ZadstatNot Available
Brand mixtures
NameLabellerIngredients
FlagystatinAventis Pharma Inc
Flagystatin CreamSanofi Aventis Canada Inc
Flagystatin Vaginal OvuleSanofi Aventis Canada Inc
PyleraPhysicians Total Care, Inc.
RosasolGlaxosmithkline Inc
Salts
Name/CASStructureProperties
Metronidazole hydrochloride
69198-10-3
Thumb
  • InChI Key: FPTPAIQTXYFGJC-UHFFFAOYSA-N
  • Monoisotopic Mass: 207.041068908
  • Average Mass: 207.615
DBSALT000362
Categories
UNII140QMO216E
CAS number443-48-1
WeightAverage: 171.154
Monoisotopic: 171.064391169
Chemical FormulaC6H9N3O3
InChI KeyInChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
IUPAC Name
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
SMILES
CC1=NC=C(N1CCO)[N+]([O-])=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentNitroimidazoles
Alternative Parents
Substituents
  • Trisubstituted imidazole
  • Nitroimidazole
  • 1,2,5-trisubstituted-imidazole
  • N-substituted imidazole
  • Heteroaromatic compound
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Alkanolamine
  • Hydrocarbon derivative
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsMetronidazole, 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 actionMetronidazole 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.
Related Articles
AbsorptionWell 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 distributionNot Available
Protein bindingLess than 20% bound to plasma proteins.
Metabolism

Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.

Route of eliminationNot Available
Half life6-8 hours
ClearanceNot Available
ToxicityLD50=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
  • Helicobacter pylori
  • Peptoclostridium difficile
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9805
Blood Brain Barrier+0.9297
Caco-2 permeable-0.5365
P-glycoprotein substrateNon-substrate0.5141
P-glycoprotein inhibitor INon-inhibitor0.8954
P-glycoprotein inhibitor IINon-inhibitor0.8755
Renal organic cation transporterNon-inhibitor0.7762
CYP450 2C9 substrateNon-substrate0.7318
CYP450 2D6 substrateNon-substrate0.8815
CYP450 3A4 substrateNon-substrate0.6767
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9242
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9401
CYP450 3A4 inhibitorNon-inhibitor0.9242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8483
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7471
BiodegradationNot ready biodegradable0.5941
Rat acute toxicity2.0422 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Non-inhibitor0.8272
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Gd searle llc
  • Able laboratories inc
  • Alembic ltd
  • Par pharmaceutical inc
  • Galderma laboratories lp
  • Altana inc
  • G and w laboratories inc
  • Sanofi aventis us llc
  • Taro pharmaceutical industries ltd
  • Tolmar inc
  • Graceway pharmaceuticals llc
  • Teva pharmaceuticals usa
  • Baxter healthcare corp
  • B braun medical inc
  • Abbott laboratories pharmaceutical products div
  • Abraxis pharmaceutical products
  • Elkins sinn div ah robins co inc
  • International medication systems ltd
  • Watson laboratories inc
  • Claris lifesciences ltd
  • Hospira inc
  • Laboratorios aplicaciones farmaceuticas sa de cv
  • Halsey drug co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lnk international inc
  • Mutual pharmaceutical co inc
  • Pliva inc
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • World gen llc
  • Ortho mcneil pharmaceutical inc
  • Savage laboratories inc div altana inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral375 mg/1
Capsuleoral500 mg
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Suppositoryvaginal500 mg
Creamvaginal10 %
Creamvaginal
Suppositoryvaginal
Tablet (extended-release)oral750 mg
Creamtopical.75 %
Geltopical10 mg/g
Geltopical0.75 %
Geltopical1 %
Lotiontopical0.75 %
Creamtopical7.5 mg/g
Geltopical7.5 mg/g
Injection, solutionintravenous500 mg/100mL
Lotiontopical7.5 mg/g
Lotiontopical7.5 mg/mL
Solutionintravenous500 mg/100mL
Tabletoral250 mg/1
Tabletoral500 mg/1
Liquidintravenous5 mg
Solutionintravenous5 mg
Gelvaginal0.75 %
Creamtopical1 %
Creamtopical10 mg/60g
Creamtopical10 mg/g
Tabletoral250 mg
Gelvaginal65 mg/5g
Capsuleoral
Kit
Creamtopical
Gelvaginal7.5 mg/g
Prices
Unit descriptionCostUnit
MetroLotion 0.75% Lotion 59ml Bottle292.66USD bottle
MetroCream 0.75% Cream 45 gm Tube281.09USD tube
Metrogel 1% Gel 60 gm Tube200.93USD tube
Metrogel 1% Kit Box200.93USD box
Metrogel 1% kit193.2USD kit
Noritate 1% Cream 60 gm Tube156.44USD tube
MetroNIDAZOLE 0.75% Lotion 59ml Bottle89.86USD bottle
MetroNIDAZOLE 0.75% Cream 45 gm Tube80.87USD tube
MetroNIDAZOLE 0.75% Gel 45 gm Tube74.0USD tube
MetroNIDAZOLE 0.75% Gel 70 gm Tube68.53USD tube
Flagyl ER 750 mg 24 Hour tablet13.2USD tablet
Flagyl er 750 mg tablet12.7USD tablet
MetroNIDAZOLE 750 mg 24 Hour tablet8.07USD tablet
Flagyl 500 mg tablet6.24USD tablet
Metrocream 0.75% cream5.99USD g
Danazol 200 mg capsule5.63USD capsule
Flagyl 375 mg capsule5.45USD capsule
Metrolotion topical 0.75%4.77USD ml
Metronidazole benz powder4.74USD g
Flagyl 250 mg tablet3.49USD tablet
Danazol 100 mg capsule2.98USD capsule
Noritate 1% cream2.51USD g
Danazol 50 mg capsule1.99USD capsule
Metronidazole powder1.65USD g
Metronidazole 0.75% cream1.34USD g
Metronidazole vaginal 0.75% gl0.94USD g
Metronidazole 500 mg tablet0.72USD tablet
Metrogel 0.75 % Gel0.69USD g
Metrogel 1 % Gel0.63USD g
Noritate 1 % Cream0.58USD g
Rosasol 1 % Cream0.57USD g
Metrocream 0.75 % Cream0.52USD g
Metrolotion 0.75 % Lotion0.52USD g
Metrogel-vaginal 0.75% gel0.51USD g
Vandazole vaginal 0.75% gel0.48USD g
Metronidazole 250 mg tablet0.44USD tablet
Flagyl 10 % Cream0.25USD g
Apo-Metronidazole 250 mg Tablet0.06USD tablet
Flagyl 5 mg/ml0.03USD ml
Metro iv 500 mg/100 ml0.03USD ml
Metronidazole 5 mg/ml0.03USD ml
Metronidazole 500 mg/100 ml0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5536743 No1993-07-162013-07-16Us
CA2470492 No2010-02-232022-11-07Canada
CA2161737 No1998-10-202015-10-30Canada
US6881726 No2002-02-212022-02-21Us
US7348317 No2002-02-212022-02-21Us
US7456207 No2004-09-222024-09-22Us
US6350468 No1998-12-142018-12-14Us
US8946276 No2012-06-282032-06-28Us
US8658678 No2008-06-272028-06-27Us
US9198858 No2012-06-282032-06-28Us
US8877792 No2008-02-022028-02-02Us
US7893097 No2008-02-192028-02-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point160.5 °CPhysProp
water solubility9500 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.02HANSCH,C ET AL. (1995)
logS-1.26ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility5.92 mg/mLALOGPS
logP-0.15ALOGPS
logP-0.46ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)3.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.87 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.22 m3·mol-1ChemAxon
Polarizability15.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.68 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0ul0-9300000000-2268b08f47fed3f6d263View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis Reference

DrugSyn.org

US2944061
General References
  1. 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:16398774 ]
  2. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [PubMed:15715599 ]
  3. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [PubMed:10676835 ]
  4. 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:12022894 ]
External Links
ATC CodesA01AB17A02BD01A02BD02A02BD03A02BD08A02BD11D06BX01G01AF01J01RA03J01RA04J01RA10J01XD01P01AB01P01AB51
AHFS Codes
  • 08:30.92
  • 84:04.04
  • 84:04.92
PDB EntriesNot Available
FDA labelDownload (115 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Metronidazole.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Metronidazole.
CapecitabineThe serum concentration of the active metabolites of Capecitabine can be increased when Capecitabine is used in combination with Metronidazole.
CarbocisteineThe risk or severity of adverse effects can be increased when Metronidazole is combined with Carbocisteine.
CitalopramMetronidazole may increase the QTc-prolonging activities of Citalopram.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Metronidazole.
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Metronidazole.
DofetilideMetronidazole may increase the QTc-prolonging activities of Dofetilide.
EthanolThe risk or severity of adverse effects can be increased when Metronidazole is combined with Ethanol.
FluorouracilThe serum concentration of Fluorouracil can be increased when it is combined with Metronidazole.
FosphenytoinThe serum concentration of Metronidazole can be decreased when it is combined with Fosphenytoin.
GoserelinMetronidazole may increase the QTc-prolonging activities of Goserelin.
LeuprolideMetronidazole may increase the QTc-prolonging activities of Leuprolide.
LopinavirThe risk or severity of adverse effects can be increased when Metronidazole is combined with Lopinavir.
MebendazoleThe risk or severity of adverse effects can be increased when Mebendazole is combined with Metronidazole.
MifepristoneMifepristone may increase the QTc-prolonging activities of Metronidazole.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Metronidazole.
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Metronidazole.
PhenobarbitalThe serum concentration of Metronidazole can be decreased when it is combined with Phenobarbital.
PhenytoinThe serum concentration of Metronidazole can be decreased when it is combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Metronidazole.
PrimidoneThe serum concentration of Metronidazole can be decreased when it is combined with Primidone.
RitonavirThe risk or severity of adverse effects can be increased when Ritonavir is combined with Metronidazole.
TegafurThe serum concentration of the active metabolites of Tegafur can be increased when Tegafur is used in combination with Metronidazole.
TipranavirThe risk or severity of adverse effects can be increased when Metronidazole is combined with Tipranavir.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Metronidazole.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
binder
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Salles JM, Salles MJ, Moraes LA, Silva MC: Invasive amebiasis: an update on diagnosis and management. Expert Rev Anti Infect Ther. 2007 Oct;5(5):893-901. [PubMed:17914922 ]
  2. Li AQ, Dai N, Yan J, Zhu YL: [Screening for metronidazole-resistance associated gene fragments of Helicobacter pylori by suppression subtractive hybridization]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2007 Sep;36(5):465-9. [PubMed:17924465 ]
  3. Edwards DI: Nitroimidazole drugs--action and resistance mechanisms. I. Mechanisms of action. J Antimicrob Chemother. 1993 Jan;31(1):9-20. [PubMed:8444678 ]
Kind
Protein
Organism
Helicobacter pylori (strain ATCC 700392 / 26695)
Pharmacological action
yes
Actions
potentiator
General Function:
Oxidoreductase activity
Specific Function:
Reduction of a variety of nitroaromatic compounds using NADPH as source of reducing equivalents; two electrons are transferred (By similarity). Capable of reducing metronidazole; inactive RdxA renders the bacterium resistant to this compound. The reduction of metronidazole generates hydroxylamine, a potent mutagen and bactericide.
Gene Name:
rdxA
Uniprot ID:
O25608
Molecular Weight:
24067.775 Da
References
  1. Sisson G, Jeong JY, Goodwin A, Bryden L, Rossler N, Lim-Morrison S, Raudonikiene A, Berg DE, Hoffman PS: Metronidazole activation is mutagenic and causes DNA fragmentation in Helicobacter pylori and in Escherichia coli containing a cloned H. pylori RdxA(+) (Nitroreductase) gene. J Bacteriol. 2000 Sep;182(18):5091-6. [PubMed:10960092 ]
  2. Chisholm SA, Owen RJ: Mutations in Helicobacter pylori rdxA gene sequences may not contribute to metronidazole resistance. J Antimicrob Chemother. 2003 Apr;51(4):995-9. Epub 2003 Mar 13. [PubMed:12654749 ]
  3. Debets-Ossenkopp YJ, Pot RG, van Westerloo DJ, Goodwin A, Vandenbroucke-Grauls CM, Berg DE, Hoffman PS, Kusters JG: Insertion of mini-IS605 and deletion of adjacent sequences in the nitroreductase (rdxA) gene cause metronidazole resistance in Helicobacter pylori NCTC11637. Antimicrob Agents Chemother. 1999 Nov;43(11):2657-62. [PubMed:10543743 ]
  4. Pisharath H, Parsons MJ: Nitroreductase-mediated cell ablation in transgenic zebrafish embryos. Methods Mol Biol. 2009;546:133-43. doi: 10.1007/978-1-60327-977-2_9. [PubMed:19378102 ]
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Clostridium pasteurianum
Pharmacological action
unknown
Actions
inhibitor
General Function:
Iron ion binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P29166
Molecular Weight:
63827.595 Da
References
  1. Kutty R, Bennett GN: Studies on inhibition of transformation of 2,4,6-trinitrotoluene catalyzed by Fe-only hydrogenase from Clostridium acetobutylicum. J Ind Microbiol Biotechnol. 2006 May;33(5):368-76. Epub 2006 Jan 28. [PubMed:16550436 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sterol 14-demethylase activity
Specific Function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular Weight:
56805.26 Da
References
  1. Ekins S, Mankowski DC, Hoover DJ, Lawton MP, Treadway JL, Harwood HJ Jr: Three-dimensional quantitative structure-activity relationship analysis of human CYP51 inhibitors. Drug Metab Dispos. 2007 Mar;35(3):493-500. Epub 2006 Dec 28. [PubMed:17194716 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 29, 2016 02:12