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Metronidazole

Catalog No. DB00916 Name DrugBank
CAS Number 443-48-1 Website http://www.ualberta.ca/
M. F. C6H9N3O3 Telephone (780) 492-3111
M. W. 171.15396 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 792

SYNONYMS

IUPAC name
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
IUPAC Traditional name
metronidazole
Brand Name
Danizol
Fossyol
Neo-Tric
Orvagil
Acromona
Bexon
Deflamon
Flagesol
Flagyl ER
Metric 21
Metrotop
Monagyl
Noritate
Trichomol
Trikojol
Vertisal
Anagiardil
Clont
Deflamon-Wirkstoff
Elyzol
Flagil
Flagyl I.V.
Klont
Metro Cream
Metrolag
Metrolyl
Metronidaz
Nidagel
Novonidazol
Protostat
Rathimed
Trichocide
Trichopal
Tricocet
Tricowas B
Trikozol
Vagimid
Zadstat
Apo-Metronidazole
Arilin
Atrivyl
Bayer 5360
Cont
Efloran
Entizol
Eumin
Flagemona
Flagyl
Flegyl
Giatricol
Gineflavir
Klion
Meronidal
Metro I.V.
Metro I.V. In Plastic Container
Metrocream
Metrogel
Metrogel-Vaginal
Metrolotion
Metromidol
Mexibol
Monasin
Nalox
Nida
Sanatrichom
Satric
Takimetol
Trichazol
Trichex
Tricho Cordes
Tricho-Gynaedron
Trichopol
Tricom
Trikacide
Trikamon
Trimeks
Trivazol
Vagilen
Wagitran
Synonyms
Metronidazole Hcl
Methronidazole
Metronidazole Benzoate
Metronidazolo
Metronidazole in Plastic Container
Metronidazol

DATABASE IDS

PubChem SID 46508911
CAS Number 443-48-1
PubChem CID 4173

PROPERTIES

Hydrophobicity(logP) -0.1
Solubility <0.1g/100mL

DETAILS

Description (English)
Item Information
Drug Groups approved
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).
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.
Pharmacology 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.
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
Biotransformation Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.
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.
Half Life 6-8 hours
Protein Binding Less than 20% bound to plasma proteins.
References
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]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • 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