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Encyclopedia > Metronidazole
Metronidazole
Systematic (IUPAC) name
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
Identifiers
CAS number 443-48-1
ATC code A01AB17 D06BX01, G01AF01, J01XD01, P01AB01
PubChem 4173
DrugBank APRD00631
Chemical data
Formula C6H9N3O3 
Mol. mass 171.15 g/mol
Pharmacokinetic data
Bioavailability 100% (oral)
59–94% (rectal)
Metabolism Hepatic
Half life 6–7 hours
Excretion Renal (60-80%), biliary (6–15%)
Therapeutic considerations
Pregnancy cat.

B2 (Au) Image File history File links Metronidazole. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A01A Stomatological preparations A01AA Caries prophylactic agents A01AA01 Sodium fluoride A01AA02 Sodium monofluorophosphate A01AA03 Olaflur A01AA04 Stannous fluoride A01AA30 Combinations A01AA51 Sodium fluoride, combinations A01AB Anti-infectives and antiseptics for local oral treatment A01AB02 Hydrogen peroxide... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... X-Ray of the bile duct during a laprascopic cholecystectomy A bile duct is any of a number of long tube-like structures that carry bile. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ...

Legal status

Prescription Only (S4)(AU) POM(UK) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... Zoloft, an antidepressant and antianxiety medication A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ...

Routes Oral, topical, rectal, IV, vaginal

Metronidazole (INN) (pronounced /mɛtrəˈnaɪdəzoʊl/) is a nitroimidazole anti-infective drug used mainly in the treatment of infections caused by susceptible organisms, particularly anaerobic bacteria and protozoa. It is marketed by Pfizer under the trade name Flagyl, and also by various generic manufacturers, who sell it at a cheaper price. Metronidazole is also used as a gel preparation in the treatment of the dermatological conditions such as rosacea (Rozex and MetroGel by Galderma) and fungating tumours (Anabact, Cambridge Healthcare Supplies). In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Four 500mg acetaminophen/paracetamol suppositories A suppository is a medicine that is inserted either into the rectum (rectal suppository) or into the vagina (vaginal suppository) where it melts. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Human female internal reproductive anatomy The vagina (from the Latin for sheath or scabbard ) is the tubular tract leading from the uterus to the exterior of the body in female mammals, or to the cloaca in female birds and some reptiles. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Nitroimidazoles are imidazole heterocycles with a nitro group that have been used to combat anaerobic bacterial and parasitic infections. ... Staphylococcus aureus - Antibiotics test plate. ... An anaerobic organism or anaerobe is any organism that does not require oxygen. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Leishmania donovani, (a species of protozoan) in a bone marrow cell (in Greek proto = first and zoa = animals) are one-celled eukaryotes (that is, unicellular microbes whose cells have membrane-bound nuclei) that commonly show characteristics usually associated with animals, mobility and heterotrophy. ... Pfizer Incorporated (NYSE: PFE) is the worlds largest research-based pharmaceutical company[1].[1] The company is based in New York City. ... Dermatology (from Greek δερμα, skin) is a branch of medicine dealing with the skin and its appendages (hair, sweat glands, etc). ... Rosacea (IPA: ) is a common but often misunderstood condition that is estimated to affect over 45 million people worldwide. ... Galderma Laboratories is a pharmaceutical company dedicated to skin products and dermatology. ... Neoplasia (new growth in Greek) is abnormal proliferation of cells in a tissue or organ. ... Tumor (American English) or tumour (British English) originally means swelling, and is sometimes still used with that meaning. ...


Metronidazole is a prodrug. It is converted in anaerobic organisms by the redox enzyme pyruvate-ferredoxin oxidoreductase. The nitro group of metronidazole is chemically reduced by ferredoxin (or a ferredoxin-linked metabolic process) and the products are responsible for disrupting the DNA helical structure, thus inhibiting nucleic acid synthesis. A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Aerobic and anaerobic bacteria can be identified by growning them in liquid culture: 1: Obligate aerobic bacteria gather at the top of the test tube in order to absorb maximal amount of oxygen. ... ed|other uses|reduction}} Illustration of a redox reaction Redox (shorthand for reduction/oxidation reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... Ferredoxin is an electron receptor used in both Cyclic and Non cyclic photophosphorylation. ... In biochemistry, an oxidoreductase is an enzyme that catalyzes the transfer of electrons from one molecule (the oxidant, also called the hydrogen donor or electron donor) to another (the reductant, also called the hydrogen acceptor or electron acceptor). ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... Look up nucleic acid in Wiktionary, the free dictionary. ...


Metronidazole is selectively taken up by anaerobic bacteria and sensitive protozoal organisms because of the ability of these organisms to reduce metronidazole to its active form intracellularly. An anaerobic organism or anaerobe is any organism that does not require oxygen. ... Leishmania donovani, (a species of protozoan) in a bone marrow cell (in Greek proto = first and zoa = animals) are one-celled eukaryotes (that is, unicellular microbes whose cells have membrane-bound nuclei) that commonly show characteristics usually associated with animals, mobility and heterotrophy. ...

Contents

Indications

Systemic metronidazole is indicated for the treatment of:

Topical metronidazole is indicated for the treatment of rosacea, and in the treatment of malodorous fungating wounds.[1] Vaginitis is an inflammation of the vaginal mucosa and often associated with an irritation or infection of the vulva leading to vulvovaginitis. ... Binomial name Trichomonas vaginalis (Donné 1836) Trichomonas vaginalis, an anaerobic, parasitic flagellated protozoan, is the causative agent of trichomoniasis, and is the most common pathogenic protozoan infection of humans in industrialized countries. ... Binomial name Gardnerella vaginalis Gardnerella is a genus of gram-variable bacteria of which Gardnerella vaginalis is the only species. ... Mycoplasma hominis is a bacteria present in the vagina that is thought to be a cause of pelvic inflammatory disease. ... Pelvic inflammatory disease (or disorder) (PID) is a generic term for infection of the female uterus, fallopian tubes, and/or ovaries as it progresses to scar formation with adhesions to nearby tissues and organs. ... Ofloxacin sold under the brand name Floxin in the US. It is a quinolone antibiotic. ... Levofloxacin is an advanced generation fluoroquinolone antibiotic, marketed by Ortho-McNeil under the trade name Levaquin in the United States. ... Ceftriaxone (INN) (IPA: ) is a third-generation cephalosporin antibiotic. ... Leishmania donovani, (a species of protozoan) in a bone marrow cell (in Greek proto = first and zoa = animals) are one-celled eukaryotes (that is, unicellular microbes whose cells have membrane-bound nuclei) that commonly show characteristics usually associated with animals, mobility and heterotrophy. ... For the infection and disease caused by this parasite, refer to Amoebiasis. ... Dysentery (formerly known as flux or the bloody flux) is frequent, small-volume, severe diarrhea that shows blood in the feces along with intestinal cramping and tenesmus (painful straining to pass stool). ... For the death metal band, see Abscess (band). ... Binomial name (Kunstler, 1882) Giardia lamblia (synonymous with Lamblia intestinalis and Giardia duodenalis) is a flagellated protozoan parasite that colonises and reproduces in the small intestine, causing giardiasis. ... Giardiasis (also known as beaver fever) is a disease caused by the flagellate protozoan Giardia lamblia (also Giardia intestinalis). ... Iodoquinol is a quinoline derivative which can be used in the treatment of amoebiasis. ... Diloxanide furoate is an anti-protozoal drug used in the treatment of Entamoeba histolytica and some other protozoal infections. ... Species etc. ... Fusobacteria contribute to several diseases, including periodontal diseases, Lemierres syndrome, and tropical skin ulcers. ... Species Clostridium acetobutylicum Clostridium aerotolerans Clostridium botulinum Clostridium colicanis Clostridium difficile Clostridium formicaceticum Clostridium novyi Clostridium perfringens Clostridium sordelli Clostridium tetani Clostridium piliforme Clostridium tyrobutyricum etc. ... Peptostreptococci, anaerobic streptococci, are Gram-positive cocci, a type of bacteria. ... An empyema is a collection of pus within a natural body cavity. ... This article is about human pneumonia. ... Aspiration pneumonia is a specific form of lung infection (pneumonia) that develops when oral or gastric contents (including food, saliva, or nasal secretions) enter the bronchial tree. ... Lung abscess is necrosis of the pulmonary tissue and formation of cavities containing necrotic debris or fluid caused by microbial infection. ... Brain abscess (or cerebral abscess) is an abscess caused by inflammation and collection of infected material coming from local (ear infection, infection of paranasal sinuses, infection of the mastoid air cells of the temporal bone, epidural abscess) or remote (lung, heart, kidney etc. ... Endometritis refers to inflammation of the endometrium, the inner lining of the uterus. ... Endocarditis is an inflammation of the inner layer of the heart, the endocardium. ... Pseudomembranous colitis is an infection of the colon often, but not always, caused by the bacterium Clostridium difficile. ... Binomial name Hall & OToole, 1935 Clostridium difficile or CDF/cdf (commonly mistaken  , alternatively and correctly pronounced ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are gram-positive, anaerobic, spore-forming rods (bacillus). ... Binomial name ((Marshall 1985) Goodwin 1989) ICD-9 code: 041. ... Peptic ulcer is a non-malignant ulcer of the stomach (called gastric ulcer) or duodenum (called duodenal ulcer). ... Neomycin is an aminoglycoside antibiotic that is found in many topical medications such as creams, ointments and eyedrops. ... This article does not cite any references or sources. ... The Therapeutic Goods Administration or TGA is the regulatory body for therapeutic goods (including medicines, medical devices, gene technology, and blood products) in Australia. ... “FDA” redirects here. ... Crohns disease (also known as regional enteritis) is a chronic, episodic, inflammatory condition of the gastrointestinal tract characterized by transmural inflammation (affecting the entire wall of the involved bowel) and skip lesions (areas of inflammation with areas of normal lining between). ... Rosacea (IPA: ) is a common but often misunderstood condition that is estimated to affect over 45 million people worldwide. ... Neoplasia (new growth in Greek) is abnormal proliferation of cells in a tissue or organ. ...


Prevention of preterm births

Metronidazole has also been used in women to prevent preterm birth associated with bacterial vaginosis, amongst other risk factors including the presence of cervicovaginal fetal fibronectin (fFN). A randomised controlled trial demonstrated that metronidazole was ineffective in preventing preterm delivery in high-risk pregnant women and, conversely, the incidence of preterm delivery was actually higher in women treated with metronidazole.[2] Bacterial vaginosis (BV) is the most common cause of vaginal infection (vaginitis). ... A randomized controlled trial (RCT) is a form of clinical trial, or scientific procedure used in the testing of the efficacy of medicine, used because of its record of reliability. ...


Lamont has argued that Metronidazole is not the right antibiotic to administer in these circumstances and was often administered too late to be of use. Clindamycin administered early in the second trimester to women who test positive for bacterial vaginosis seems to be more effective.[3] Clindamycin (rINN) (IPA: ) is a lincosamide antibiotic used in the treatment of infections caused by susceptible microorganisms. ... Bacterial vaginosis (BV) is the most common cause of vaginal infection (vaginitis). ...


Adverse effects

Common adverse drug reactions (≥1% of patients) associated with systemic metronidazole therapy include: nausea, diarrhea, and/or metallic taste in the mouth. Intravenous administration is commonly associated with thrombophlebitis. Infrequent adverse effects include: hypersensitivity reactions (rash, itch, flushing, fever), headache, dizziness, vomiting, glossitis, stomatitis, dark urine, and/or paraesthesia.[1] An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Systemic Relating to, or affecting a particular body system; especially the nervous system. ... For other uses, see Nausea (disambiguation). ... Diarrhea, also spelled diarrhoea (see spelling differences), is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause of death in developing countries (particularly among infants), accounting for 5 to 8 million deaths... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... It has been suggested that this article or section be merged into deep vein thrombosis. ... Hypersensitivity refers to undesirable (damaging, discomfort-producing and sometimes fatal) reactions produced by the normal immune system. ... Emesis redirects here. ... Glossitis is inflammation or infection of the tongue. ... Stomatitis is an inflammation of the mucous lining of any of the structures in the mouth, which may involve the cheeks, gums, tongue, lips, and roof or floor of the mouth. ... Paresthesia (paraesthesia in British) is a sensation of tingling, pricking, or numbness of the skin with no apparent physical cause, more generally known as the feeling of pins and needles. ...


High doses and/or long-term systemic treatment with metronidazole is associated with the development of black hairy tongue, leukopenia, neutropenia, increased risk of peripheral neuropathy and/or CNS toxicity.[1] A picture of Black hairy tongue. ... Leukopenia or leukocytopenia refers to a decrease in the number of circulating white blood cells (leukocytes) in the blood. ... Neutropenia (or neutropaenia, adjective neutrop(a)enic) is a hematological disorder characterized by an abnormally low number of neutrophil granulocytes (a type of white blood cell). ... Peripheral neuropathy is the term for damage to nerves of the peripheral nervous system, which may be caused either by diseases of the nerve or from the side-effects of systemic illness. ... A diagram showing the CNS: 1. ...


Metronidazole is listed by the International Agency for Research on Cancer (IARC) as a potential human carcinogen. Although some of the testing methods have been questioned, it has been shown to cause cancer in experimental animals.[4] Nevertheless, it appears to have a fairly low potential for cancer risk and under most circumstances the benefits of treatment outweighs the risk. The International Agency for Research on Cancer (IARC, or CIRC in its French acronym) is an intergovernmental agency forming part of the World Health Organisation of the United Nations. ... Look up carcinogen in Wiktionary, the free dictionary. ...


Common adverse drug reactions associated with topical metronidazole therapy include local redness, dryness, and/or skin irritation; and eye watering (if applied near eyes).[1]


Interaction with alcohol

Consuming ethanol (alcohol) while using metronidazole causes a disulfiram-like reaction with effects that can include nausea, vomiting, flushing of the skin, tachycardia (accelerated heart rate), shortness of breath, and even death.[5] Consumption of alcohol should be avoided by patients during systemic metronidazole therapy and for at least 24 hours after completion of treatment.[1] However, the occurrence of this reaction in the clinical setting has recently been questioned by some authors.[6][7] Grain alcohol redirects here. ... Disulfiram is a drug used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol. ... For other uses, see Nausea (disambiguation). ... Emesis redirects here. ... For a person to flush is to become markedly red in the face and often other areas of the skin, from various physiological conditions. ... This article or section does not cite any references or sources. ... Dyspnea (Latin dyspnoea, Greek dyspnoia from dyspnoos - short of breath) or shortness of breath (SOB) is perceived difficulty breathing or pain on breathing. ...


References

  1. ^ a b c d e (2006) in Rossi S: Australian Medicines Handbook 2006. Australian Medicines Handbook Pty Ltd, Adelaide. ISBN 0-9757919-2-3. 
  2. ^ Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, et al. (2006). "A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study". BJOG 113 (1): 65-74. PMID 16398774. 
  3. ^ Lamont RF (2005). "Can antibiotics prevent preterm birth—the pro and con debate". BJOG 112(suppl): 67-73. PMID 15715599. 
  4. ^ National Toxicology Program. Metronidazole. In: Report on carcinogens. 11th ed. Research Triangle Park (NC): U.S. Department of Health and Human Services. [updated 2005 Aug 26; cited 2006 Jun 20]. Available from: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s112metr.pdf
  5. ^ Stephen J Cina, Roger A Russell, Sandra E Conradi (1996). "Sudden death due to metronidazole/ethanol interaction". American Journal of Forensic Medical Pathology 17 (4): 343-346. 
  6. ^ Williams CS, Woodcock KR (2000). "Do ethanol and metronidazole interact to produce a disulfiram-like reaction?". Ann Pharmacother 34 (2): 255-7. PMID 10676835. 
  7. ^ Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP (2002). "Lack of disulfiram-like reaction with metronidazole and ethanol". Ann Pharmacother 36 (6): 971-4. PMID 12022894. 

The Australian Medicines Handbook or AMH is a medical reference text commonly used in practice by health professionals (particularly general practitioners and pharmacists) in Australia. ...

External links

  • Merck manuals

  Results from FactBites:
 
Metronidazole For Veterinary Use (1013 words)
Metronidazole is an antibiotic which is commonly used to treat protozoal infections and anaerobic bacterial infections.
Metronidazole may be used with corticosteroids in the treatment of inflammatory bowel disease, or gum disease (gingivitis/stomatitis) in cats.
Metronidazole is primarily used with other antibiotics to treat mixed bacterial infections in which anaerobic bacteria are present, for example, pleuropneumonia, peritonitis, and abdominal abscesses.
Metronidazole- Health Encyclopedia and Reference (0 words)
Metronidazole is an antiprotozoal drug with antibacterial effects.
Metronidazole belongs to the family of medicines called anti-infectives.
Metronidazole should not be used in the first trimester of pregnancy.
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