Product Name

Metronidazole

CAS Number

443-48-1

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Product Name:
Metronidazole
CAS Number:
443-48-1
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.
Mode 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.

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.

Metabolism:

Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.

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).

IUPAC:
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
ATC:
A01AB17" D06BX01" G01AF01" J01XD01" P01AB01
PubChem:
4173
DrugBank:
DB00916 (APRD00631)
Formula:
C6H9N3O3
Molecular Mass:
171.154
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, 2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazole, 2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazole, 2-Methyl-5-nitroimidazole-1-ethanol, 5-23-05-00063 (Beilstein Handbook Reference), Acromona, Anagiardil, Arilin, Atrivyl, Bayer 5360, Bexon, BRN 0611683, Caswell No. 579AA, CCRIS 410, Clont, CONT, Danizol, Deflamon, Deflamon-wirkstoff, Efloran, EINECS 207-136-1, Elyzol, Entizol, EPA Pesticide Chemical Code 120401, Eumin, Flagemona, Flagesol, Flagil, Flagyl, Flagyl ER, Flagyl I.V. rtu in plastic container, Fossyol, Giatricol, Gineflavir, HSDB 3129, Klion, Klont, Meronidal, Metro Gel, Metro I.V., Metro I.V. in plastic container, Metrocream, Metrogel, MetroGel-Vaginal, Metrolotion, Metromidol, Metronidaz, Metronidazol, Metronidazol [INN-Spanish], Metronidazole, Metronidazole in plastic container, Metronidazolo, Metronidazolo [DCIT], Metronidazolum, Metronidazolum [INN-Latin], Mexibol, Mexibol 'silanes', Monagyl, Monasin, Nalox, Neo-tric, NIDA, Noritate, Novonidazol, NSC 50364, NSC 69587, NSC-50364, Orvagil, Protostat, RP 8823, Sanatrichom, Satric, SC 10295, Takimetol, Trichazol, Trichex, Trichocide, Trichomol, Trichomonacid 'pharmachim', Trichopol, Tricocet, Tricom, Tricowas B, Trikacide, Trikamon, Trikojol, Trikozol, Trimeks, Trivazol, UNII-140QMO216E, Vagilen, Vagimid, Vandazole, Vertisal, Wagitran
SMILES:
CC1=NC=C(N1CCO)[N+]([O-])=O
AHFS Code:
84:04.92, 84:04.04, 08:30.92
InChi:
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
General Reference:
General Reference:

 

  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
  2. Lamont RF: Can antibiotics prevent preterm birth—the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed
  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
  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

 

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