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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/13 22:41:02」(JST)

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Metronidazole (INN) /mɛtrəˈnaɪdəzoʊl/ (Flagyl, and others) is a nitroimidazole antibiotic medication used particularly for anaerobic bacteria and protozoa. Metronidazole is an antibiotic, amebicide, and antiprotozoal.^[1] It is the drug of choice for first episodes of mild-to-moderate Clostridium difficile infection.^[2] It is marketed in the United States by Pfizer and globally by Sanofi under the trade name Flagyl, and is also sold under other brand names. Metronidazole was developed in 1960.

Metronidazole is used also 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).

1 Medical uses
- 1.1 Bacterial
- 1.2 Protozoal
- 1.3 Nonspecific
- 1.4 Preterm births
- 1.5 Veterinary use
2 Adverse effects
- 2.1 Central nervous system
- 2.2 Interaction with alcohol
- 2.3 Stevens–Johnson syndrome
- 2.4 Serotonin syndrome
3 Mechanism of action
4 Synthesis
5 References
6 External links

Medical uses[edit source | edit]

Metronidazole is indicated for the treatment of:

Bacterial[edit source | edit]

Bacterial vaginosis, commonly associated with overgrowth of Gardnerella species and coinfective anaerobes (Mobiluncus, Bacteroides), in symptomatic patients

Pelvic inflammatory disease in conjunction with other antibiotics such as ofloxacin, levofloxacin, or ceftriaxone

Anaerobic infections such as Bacteroides fragilis, spp, Fusobacterium spp, Clostridium spp, Peptostreptococcus spp, Prevotella spp, or any other anaerobes in intra-abdominal abscess, peritonitis, diverticulitis, empyema, pneumonia, aspiration pneumonia, lung abscess, diabetic foot ulcer, meningitis and brain abscesses, bone and joint infections, septicemia, endometritis, or endocarditis

Pseudomembranous colitis due to Clostridium difficile

Helicobacter pylori eradication therapy, as part of a multi-drug regimen in peptic ulcer disease

Dental infection of bacterial origin, such as periapical abscess, periodontal abscess, acute pericoronitis of impacted or partially erupted teeth; often used in conjunction with Amoxicillin

Protozoal[edit source | edit]

Amoebiasis: Infections caused by Entamoeba histolytica.^[1]

Giardiasis: infection of the small intestine caused by the ingestion of infective cysts of protozoan Giardia lamblia.^[1]

Trichomoniasis: infection caused by Trichomonas vaginalis, which is a common cause of vaginitis and is the most frequently presenting new infection of the common sexually transmitted diseases.^[1]

Nonspecific[edit source | edit]

Prophylaxis for those undergoing potentially contaminated colorectal surgery or appendectomies and may be combined with neomycin^{[citation needed]}

Crohn's disease with colonic or perianal involvement (not approved by the U.S. Food and Drug Administration) – believed to be more effective in combination with ciprofloxacin^{[citation needed]}

Topical metronidazole is indicated for the treatment of rosacea, and in the treatment of malodorous fungating wounds.^[3]

Preterm births[edit source | edit]

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.^[4]

In a study it has been found that metronidazole is not the right antibiotic to administer in these circumstances and that it was often administered too late to be of use. Clindamycin administered early in the second trimester to women who test positive for bacterial vaginosis seemed to be more effective.^[5]

Veterinary use[edit source | edit]

Metronidazole is not labeled for animal use but is widely used to treat infections of Giardia in dogs, cats, and other companion animals, although it does not reliably clear infection with this organism and is being supplanted by Fenbendazole for this purpose in dogs and cats.^[6] Metronidazole is also used for the management of chronic inflammatory bowel disease in cats and dogs.^[7] Another common usage is the treatment of systemic and/or GI clostridial infections in horses. Metronidazole or simply "Metro" is used in the aquarium hobby to treat ornamental fish and as a wide spectrum treatment for bacterial and protozoan infections in reptiles and amphibians. It is also used to treat human enteric (gi) and systemic infections. In general, the veterinary community may use metronidazole for any potentially susceptible anaerobic infection. The U.S. Food and Drug Administration (FDA) suggests that it only be used when necessary because it has been shown to be carcinogenic in mice and rats as well as the microbes that it is prescribed to fight. The main reason that it should be used sparingly, however, is the fact that it still works, thus it shouldn't be abused lest the microbes develop a resistance.^[8] ^[9]

Adverse effects[edit source | edit]

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.^[3]

High doses and/or long-term systemic treatment with metronidazole is associated with the development of leukopenia, neutropenia, increased risk of peripheral neuropathy and/or CNS toxicity.^[3]

Metronidazole is listed by the US National Toxicology Program (NTP) as reasonably anticipated to be a human carcinogen^{[citation needed]}. Although some of the testing methods have been questioned, oral exposure has been shown to cause cancer in experimental animals.^[10] The relationship between exposure to metronidazole and human cancer is unclear.^[10] One study (Beard et al. 1988) found an excess in lung cancer among women (even after adjusting for smoking), while other studies (IARC 1987; Thapa et al. 1998) found either no increased risk, or a statistically insignificant risk.^[10] ^[11] Metronidazole is listed as a possible carcinogen according to the WHO International Agency for Research on Cancer (IARC).^[12]

Due to its potential carcinogenic properties, metronidazole is banned in the EU and the USA for veterinary use in the feed of animals and is banned for use in any food animals in the USA.^[13]^[14] In the USA, this type of restriction is covered under the Delaney clause.

Earlier studies suggested a relation between metronidazole and various birth defects. Those studies are now considered flawed and more recent studies "do not support a significant increased risk for birth defects or other adverse effects on the fetus."^[15]

Common adverse drug reactions associated with topical metronidazole therapy include local redness, dryness, and/or skin irritation; and eye watering (if applied near eyes).^[3]

Central nervous system[edit source | edit]

Metronidazole toxicity is rare (though the actual incidence is not known with certainty). Toxic levels of metronidazole can cause symmetrical lesions in the brain in the corpus callosum and dentate nuclei. Patients present with nausea, vomiting, dysarthria, vertigo, and confusion. Other side effects of the metronidazole can include dry mouth, diarrhea, headache, dizziness, or peripheral neuropathy. An examination of a patient reveals that the patient is confused and has dysarthria (difficult or unclear articulation of speech that is otherwise linguistically normal), ataxia (loss of full control of bodily movements), abnormal eye movements including nystagmus and ophthalmoparesis.

Magnetic resonance imaging (MRI) most often shows bilateral symmetric hyperintense lesions of the dentate nuclei in FLAIR (fluid-attenuated inversion recovery) sequences, as well as symmetric lesions of the corpus callosum and basal ganglia. Most reports have been seen in patients who receive approximately one gram a day of metronidazole for over 30 days.^[16]^[17]^[18]

Interaction with alcohol[edit source | edit]

Consuming ethanol (alcohol) while taking metronidazole has long been thought to have a disulfiram-like reaction with effects that can include nausea, vomiting, flushing of the skin, tachycardia (accelerated heart rate), and shortness of breath.^[19] Typically a 2006 Medicines Handbook warns that consumption of alcohol should be avoided by patients during systemic metronidazole therapy and for at least 48 hours after completion of treatment.^[3] However there are studies calling into question the interaction of alcohol and metronidazole,^[20] and the mechanism of this reaction in the clinical setting has been questioned by some authors,^[21]^[22] and a possible central toxic serotonin reaction for the alcohol intolerance suggested.^[23] Metronidazole is also generally thought to inhibit the liver metabolism of propylene glycol (found in some foods, medicines and in many electronic cigarette e-liquids), and thus propylene glycol may potentially have similar interaction effects with metronidazole.

Stevens–Johnson syndrome[edit source | edit]

Metronidazole alone rarely causes Stevens–Johnson syndrome but is reported to occur at high rates when combined with mebendazole.^[24]

Serotonin syndrome[edit source | edit]

Serotonin syndrome has been reported with metronidazole. Symptoms may appear within minutes of oral dosage, and/or days to months. Signs and symptoms may include: increased heart rate, shivering, sweating, dilated pupils, twitching, over-responsive reflexes, hyperthermia, fever, confusion, hyper-vigilance, agitation, muscle rigidity, headache, elevated blood pressure, and changes in blood chemistry. The only direct treatment is to discontinue the offending drugs.^[23]^[25]

Mechanism of action[edit source | edit]

Metronidazole, taken up by diffusion, is selectively absorbed by anaerobic bacteria and sensitive protozoa. Once taken up by anaerobes, it is non-enzymatically reduced by reacting with reduced ferredoxin, which is generated by pyruvate oxido-reductase. Many of the reduced nitroso intermediates will form sulfinamides and thioether linkages with cysteine-bearing enzymes, thereby deactivating these critical enzymes. As many as 150 separate enzymes are affected.

In addition or alternatively, the metronidazole metabolites are taken up into bacterial DNA, and form unstable molecules. This function only occurs when metronidazole is partially reduced, and because this reduction usually happens only in anaerobic cells, it has relatively little effect upon human cells or aerobic bacteria.^[26]

Synthesis[edit source | edit]

2-Methylimidazole (1) may be prepared via the Debus-Radziszewski imidazole synthesis, or from ethylenediamine and acetic acid, followed by treatment with lime, then Raney nickel. 2-Methylimidazole nitrated to give 2-methyl-4(5)-nitroimidazole (2), which is in turn alkylated with ethylene oxide or 2-chloroethanol to give metronidazole (3):^[27]^[28]^[29]

References[edit source | edit]

^ ^a ^b ^c ^d "Metronidazole monograph". drugs.com.
^ Cohen, S. H.; Gerding, D. N.; Johnson, S.; Kelly, C. P.; Loo, V. G.; McDonald, L. C.; Pepin, J.; Wilcox, M. H.; Society for Healthcare Epidemiology of America; Infectious Diseases Society of America (2010). "Clinical Practice Guidelines for Clostridium difficile Infection in Adults: 2010 Update by the Society for Healthcare Epidemiology of America (SHEA) and the Infectious Diseases Society of America (IDSA)". Infection Control and Hospital Epidemiology 31 (5): 431–455. doi:10.1086/651706. PMID 20307191. edit
^ ^a ^b ^c ^d ^e Rossi, Simone, ed. (2006). Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook Pty. ISBN 978-0-9757919-2-9. OCLC 224831213. ^{[page needed]}
^ Shennan, A.; Crawshaw, S.; Briley, A.; Hawken, J.; Seed, P.; Jones, G.; Poston, L. (2005). "General obstetrics: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: The PREMET Study". BJOG: An International Journal of Obstetrics and Gynaecology 113 (1): 65–74. doi:10.1111/j.1471-0528.2005.00788.x. PMID 16398774. edit
^ Lamont, R. F. (2005). "Can antibiotics prevent preterm birth-the pro and con debate". BJOG: An International Journal of Obstetrics and Gynaecology 112 (Suppl 1): 67–73. doi:10.1111/j.1471-0528.2005.00589.x. PMID 15715599. edit
^ Barr, S. C.; Bowman, D. D.; Heller, R. L. (1994). "Efficacy of fenbendazole against giardiasis in dogs". American Journal of Veterinary Research 55 (7): 988–990. PMID 7978640. edit
^ Johnny D., Hoskins,. "DVM, PhD, Dipl. ACVIM". dvm360. Retrieved 23 July 2012.
^ Plumb, Donald C. (2008). Veterinary Drug Handbook (6 ed.). Wiley, John & Sons. ISBN 0-8138-2056-1.
^ http://www.drugs.com/pro/metronidazole.html
^ ^a ^b ^c "Metronidazole CAS No. 443-48-1" (pdf). Report on Carcinogens, Twelfth Edition (2011). U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program. Retrieved 2011-10-28.
^ "Flagyl 375 U.S. Prescribing Information" (pdf). Pfizer.
^ "Agents Classified by the IARC Monographs, Volumes 1–100" (PHP). International Agency for Research on Cancer (IARC). World Health Organization. May 2010. Retrieved 2010-06-06.
^ "Metronidazole Summary Report EMEA/MRL/173/96-FINAL" (pdf). Committee for Medicinal Products for Veterinary Use (CVMP). European Medicines Agency. July 1997. Retrieved 2009-12-11.
^ "FDA's prohibited drug list". Food Animal Residue Avoidance and Depletion Program (FARAD). U.S. Food and Drug Administration. 2010. Retrieved 2010-06-06.
^ "Metronidazole (Flagyl) and Pregnancy" (pdf). OTIS pregnancy.
^ Aaron Lord. Department of Neurology, Columbia University. Case Report.
^ Kuriyama, A.; Jackson, J. L.; Doi, A.; Kamiya, T. (2011). "Metronidazole-Induced Central Nervous System Toxicity". Clinical Neuropharmacology 34 (6): 1. doi:10.1097/WNF.0b013e3182334b35. PMID 21996645. edit
^ Sinha, S.; Pramod, A.; Sinha, P. S.; Saini, A. B.; Mahadevan, J.; Bharath, K.; Bindu, J.; Yasha, R. D. et al. (2011). "Clinical, neuroimaging and pathological features of 5-nitroimidazole-induced encephalo-neuropathy in two patients: Insights into possible pathogenesis". Neurology India 59 (5): 743–747. doi:10.4103/0028-3886.86552. PMID 22019662. |displayauthors= suggested (help) edit
^ Cina, S. J.; Russell, R. A.; Conradi, S. E. (1996). "Sudden death due to metronidazole/ethanol interaction". The American Journal of Forensic Medicine and Pathology 17 (4): 343–346. PMID 8947362. edit
^ Gupta, N. K.; Woodley, C. L.; Fried, R. (1970). "Effect of metronidazole on liver alcohol dehydrogenase". Biochemical Pharmacology 19 (10): 2805–2808. doi:10.1016/0006-2952(70)90108-5. PMID 4320226. edit
^ Williams CS, Woodcock KR (2000). "Do ethanol and metronidazole interact to produce a disulfiram-like reaction?". The Annals of Pharmacotherapy 34 (2): 255–7. doi:10.1345/aph.19118. PMID 10676835. "the authors of all the reports presumed the metronidazole-ethanol reaction to be an established pharmacologic fact. None provided evidence that could justify their conclusions"
^ Visapää, J. P.; Tillonen, J. S.; Kaihovaara, P. S.; Salaspuro, M. P. (2002). "Lack of disulfiram-like reaction with metronidazole and ethanol". The Annals of Pharmacotherapy 36 (6): 971–974. PMID 12022894. edit
^ ^a ^b Karamanakos, P.; Pappas, P.; Boumba, V.; Thomas, C.; Malamas, M.; Vougiouklakis, T.; Marselos, M. (2007). "Pharmaceutical Agents Known to Produce Disulfiram-Like Reaction: Effects on Hepatic Ethanol Metabolism and Brain Monoamines". International Journal of Toxicology 26 (5): 423–432. doi:10.1080/10915810701583010. PMID 17963129. edit
^ Chen KT, Twu SJ, Chang HJ, Lin RS (2003). "Outbreak of Stevens-Johnson Syndrome/Toxic Epidermal Necrolysis Associated with Mebendazole and Metronidazole Use Among Filipino Laborers in Taiwan". American Journal of Public Health 93 (3): 489–492. PMC 1447769. PMID 12604501. edit
^ Karamanakos, P. N. (2008). "The possibility of serotonin syndrome brought about by the use of metronidazole". Minerva Anestesiologica 74 (11): 679. PMID 18971895. edit
^ Eisenstein, B. I.; Schaechter, M. (2007). "DNA and Chromosome Mechanics". In Schaechter, M.; Engleberg, N. C.; DiRita, V. J. et al. Schaechter's Mechanisms of Microbial Disease. Hagerstown, MD: Lippincott Williams & Wilkins. p. 28. ISBN 978-0-7817-5342-5. |displayeditors= suggested (help)
^ Ebel, K.; Koehler, H.; Gamer, A. O.; Jäckh, R. (2005), "Imidazole and Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_661
^ Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. (2005), "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_173
^ Kraft, M. Ya.; Kochergin, P. M.; Tsyganova, A. M.; Shlikhunova, V. S. (1989). "Synthesis of metronidazole from ethylenediamine". Pharmaceutical Chemistry Journal 23 (10): 861–863. doi:10.1007/BF00764821.

External links[edit source | edit]

"Metronidazole for veterinary use". Wedgewood pharmacy.

"Metronidazole". Merck manuals.

"Metronidazole". patient.co.uk.

"Metronidazole". Drug Information Portal. U.S. National Library of Medicine.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. メトロニダゾール：概要 metronidazole an overview
2. マクロライド系剤、アミノグリコシド、テトラサイクリン、クリンダマイシン、およびメトロニダゾールに対する過敏反応 hypersensitivity reactions to macrolides aminoglycosides tetracyclines clindamycin and metronidazole
3. Intracranial epidural abscess
4. Antimicrobial approach to intra-abdominal infections in adults
5. 経膣メッシュ曝露と骨盤手術後の疼痛のマネージメント management of transvaginal mesh exposure and pain following pelvic surgery

English Journal

Metronidazole-loaded nanostructured lipid carriers to improve skin deposition and retention in the treatment of rosacea.

Shinde UA, Parmar SJ, Easwaran S.
Drug development and industrial pharmacy. 2019 Jul;45(7)1039-1051.
The objective of the present investigation was to improve the skin deposition and retention of metronidazole (MTZ) in rosacea therapy by incorporating it into nanostructured lipid carriers (NLCs). The main challenge in this endeavor was the partial hydrophilicity of MTZ, which mandated careful selec
PMID 30727789

Infection-responsive electrospun nanofiber mat for antibacterial guided tissue regeneration membrane.

Shi R, Ye J, Li W, Zhang J, Li J, Wu C, Xue J, Zhang L.
Materials science & engineering. C, Materials for biological applications. 2019 Jul;100()523-534.
The release of anti-infection drugs in a targeted and efficient manner in response to the attack time and degree of severity of infection is a requirement of new generation implants. Herein, we design an infection-responsive guided tissue regeneration (GTR)/guided bone regeneration (GBR) membrane ba
PMID 30948089

Biocompatible chitosan-pectin polyelectrolyte complex for simultaneous electrochemical determination of metronidazole and metribuzin.

Ranganathan P, Mutharani B, Chen SM, Sireesha P.
Carbohydrate polymers. 2019 Jun;214()317-327.
Development of novel biocompatible sensor material suitable for modest, cost-effective, and rapid practical application is a demanding research interest in the field of electroanalytical chemistry. In this context, for the first time, we utilized biocompatible chitosan-pectin biopolyelectrolyte (CS-
PMID 30926003

Japanese Journal

Clinical evaluation of unani medicine for infective vaginal discharge

NAZAR Halima,USMANGHANI Khan,HANNAN Abdul
和漢医薬学雑誌 22(6), 301-307, 2005-12-20
… The study is an experimental, randomized, prospective, multi center, clinical trial to compare the effectiveness and safety of coded herbal medicinal treatments Leuko-off and the screening of antifungal activity Leuko-off and Gynosporin, antibacterial activity Leuko-off and Enoxabid and antiprotozoal activity of Leuko-off and Flagyl were carried out respectively. …
NAID 110002976883

アメーバ性膿胸の1例 : 胸水細胞像ならびに組織像について

根本則道,小松京子,関利美,斉藤俊夫,稲庭義巳,絹川典子,桜井勇
日本臨床細胞学会雑誌 30(6), 1098-1102, 1991-11
NAID 110001425156

Related Pictures

ドラッグ・エクスプレス-海外医薬品個人輸入のオンライン Flagyl 500 mg, 10 ovule | Catena | Preturi mici! Mis amigas las palomas: Tricomoniasis Metronidazole, Aka Flagyl® | Greyhound Articles Online Dicas da Farmácia Úteis: Flagyl: anti-infecioso e antiparasitário Skyexitservice - 商品説明フラジール(Flagyl)500mg | ペットのお薬119番 metronidazole 500 mg

★リンクテーブル★

リンク元	「メトロニダゾール」「metric」

「メトロニダゾール」

Metronidazole
Systematic (IUPAC) name
	2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
Clinical data
Trade names	Flagyl, Filmet
AHFS/Drugs.com	monograph
Pregnancy cat.	B (US) B2 (Au)
Legal status	Prescription Only (S4) (AU) POM (UK) ℞-only (US)
Routes	oral, topical, rectal, IV, vaginal
Pharmacokinetic data
Bioavailability	100% (oral); 59–94% (rectal)
Metabolism	Hepatic
Half-life	6–7 hours
Excretion	Renal (60-80%), biliary (6–15%)
Identifiers
CAS number	443-48-1
ATC code	A01AB17 , D06BX01, G01AF01, J01XD01, P01AB01, QP51AA01
PubChem	CID 4173
DrugBank	DB00916
ChemSpider	4029
UNII	140QMO216E
KEGG	D00409
ChEBI	CHEBI:6909
ChEMBL	CHEMBL137
NIAID ChemDB	007953
Chemical data
Formula	C6H9N3O3
Mol. mass	171.15 g/mol
	InChI InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 ; Key:VAOCPAMSLUNLGC-UHFFFAOYSA-N ;
Physical data
Melt. point	159–163 °C (318–325 °F)
(what is this?) (verify);

　　[★]

英: metronidazole, MTZ
商: フラジール Flagyl, Metro-IV、アスゾール。ランピオンパック(ランソプラゾール、アモキシシリン、メトロニダゾール)
関: トリコモナス

first aid step1 2006 p.139,142,148,165,172,178,208,276,282

特徴

原虫(トリコモナスなど)による感染症に対して用いる

構造

作用機序 PPC. 641, 647

メトロニダゾールの活性化には嫌気性生物の発酵に関与する酵素 pyruvate-derredocin oxidoreductase,PFORが必要
pyruvate-ferredoxin oxidoreductaseはferredoxinをreduced ferredoxinに変換するが、これに共役してメトロニダゾールがreduced metronidazole(活性型)に変換される。

PFORは宿主細胞(好気性生物)には存在しないので、原虫や嫌気性生物が特異的に障害を受ける

微生物の蛋白質、膜、DNAに傷害を与える

適応

USMLE (first aid step1 2006 p.172)

横隔膜より下の嫌気性菌に対して用いられる

原虫：Giardia, Entamoeba, Trichomonas
嫌気性菌：Bacteroides, Clostridium
細菌：Clostridium difficile, Helicobacter pylori, Gardnerella vaginalis

H. pylori：bismuth + amoxicillin/tetracycline + metronidazole

副作用

disulfiram-like reaction with alcohol; headache,metallic taste (first aid step1 2006 p.172)

「metric」

　　[★]

計量

関: Flagyl、meter、metronidazole

[monograph-1] "Metronidazole monograph". drugs.com.

[2] Cohen, S. H.; Gerding, D. N.; Johnson, S.; Kelly, C. P.; Loo, V. G.; McDonald, L. C.; Pepin, J.; Wilcox, M. H.; Society for Healthcare Epidemiology of America; Infectious Diseases Society of America (2010). "Clinical Practice Guidelines for Clostridium difficile Infection in Adults: 2010 Update by the Society for Healthcare Epidemiology of America (SHEA) and the Infectious Diseases Society of America (IDSA)". Infection Control and Hospital Epidemiology 31 (5): 431–455. doi:10.1086/651706. PMID 20307191. edit

[AMH2006-3] Rossi, Simone, ed. (2006). Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook Pty. ISBN 978-0-9757919-2-9. OCLC 224831213. ^{[page needed]}

[Shennan2006-4] Shennan, A.; Crawshaw, S.; Briley, A.; Hawken, J.; Seed, P.; Jones, G.; Poston, L. (2005). "General obstetrics: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: The PREMET Study". BJOG: An International Journal of Obstetrics and Gynaecology 113 (1): 65–74. doi:10.1111/j.1471-0528.2005.00788.x. PMID 16398774. edit

[Lamont2005-5] Lamont, R. F. (2005). "Can antibiotics prevent preterm birth-the pro and con debate". BJOG: An International Journal of Obstetrics and Gynaecology 112 (Suppl 1): 67–73. doi:10.1111/j.1471-0528.2005.00589.x. PMID 15715599. edit

[6] Barr, S. C.; Bowman, D. D.; Heller, R. L. (1994). "Efficacy of fenbendazole against giardiasis in dogs". American Journal of Veterinary Research 55 (7): 988–990. PMID 7978640. edit

[7] Johnny D., Hoskins,. "DVM, PhD, Dipl. ACVIM". dvm360. Retrieved 23 July 2012.

[8] Plumb, Donald C. (2008). Veterinary Drug Handbook (6 ed.). Wiley, John & Sons. ISBN 0-8138-2056-1.

[9] ttp://www.drugs.com/pro/metronidazole.html

[RoC-10] "Metronidazole CAS No. 443-48-1" (pdf). Report on Carcinogens, Twelfth Edition (2011). U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program. Retrieved 2011-10-28.

[11] "Flagyl 375 U.S. Prescribing Information" (pdf). Pfizer.

[12] "Agents Classified by the IARC Monographs, Volumes 1–100" (PHP). International Agency for Research on Cancer (IARC). World Health Organization. May 2010. Retrieved 2010-06-06.

[13] "Metronidazole Summary Report EMEA/MRL/173/96-FINAL" (pdf). Committee for Medicinal Products for Veterinary Use (CVMP). European Medicines Agency. July 1997. Retrieved 2009-12-11.

[14] "FDA's prohibited drug list". Food Animal Residue Avoidance and Depletion Program (FARAD). U.S. Food and Drug Administration. 2010. Retrieved 2010-06-06.

[otis-15] "Metronidazole (Flagyl) and Pregnancy" (pdf). OTIS pregnancy.

[16] Aaron Lord. Department of Neurology, Columbia University. Case Report.

[17] Kuriyama, A.; Jackson, J. L.; Doi, A.; Kamiya, T. (2011). "Metronidazole-Induced Central Nervous System Toxicity". Clinical Neuropharmacology 34 (6): 1. doi:10.1097/WNF.0b013e3182334b35. PMID 21996645. edit

[18] Sinha, S.; Pramod, A.; Sinha, P. S.; Saini, A. B.; Mahadevan, J.; Bharath, K.; Bindu, J.; Yasha, R. D. et al. (2011). "Clinical, neuroimaging and pathological features of 5-nitroimidazole-induced encephalo-neuropathy in two patients: Insights into possible pathogenesis". Neurology India 59 (5): 743–747. doi:10.4103/0028-3886.86552. PMID 22019662. |displayauthors= suggested (help) edit

[cina-19] Cina, S. J.; Russell, R. A.; Conradi, S. E. (1996). "Sudden death due to metronidazole/ethanol interaction". The American Journal of Forensic Medicine and Pathology 17 (4): 343–346. PMID 8947362. edit

[20] Gupta, N. K.; Woodley, C. L.; Fried, R. (1970). "Effect of metronidazole on liver alcohol dehydrogenase". Biochemical Pharmacology 19 (10): 2805–2808. doi:10.1016/0006-2952(70)90108-5. PMID 4320226. edit

[Williams2000-21] Williams CS, Woodcock KR (2000). "Do ethanol and metronidazole interact to produce a disulfiram-like reaction?". The Annals of Pharmacotherapy 34 (2): 255–7. doi:10.1345/aph.19118. PMID 10676835. "the authors of all the reports presumed the metronidazole-ethanol reaction to be an established pharmacologic fact. None provided evidence that could justify their conclusions"

[Visapaa2002-22] Visapää, J. P.; Tillonen, J. S.; Kaihovaara, P. S.; Salaspuro, M. P. (2002). "Lack of disulfiram-like reaction with metronidazole and ethanol". The Annals of Pharmacotherapy 36 (6): 971–974. PMID 12022894. edit

[pmid17963129-23] Karamanakos, P.; Pappas, P.; Boumba, V.; Thomas, C.; Malamas, M.; Vougiouklakis, T.; Marselos, M. (2007). "Pharmaceutical Agents Known to Produce Disulfiram-Like Reaction: Effects on Hepatic Ethanol Metabolism and Brain Monoamines". International Journal of Toxicology 26 (5): 423–432. doi:10.1080/10915810701583010. PMID 17963129. edit

[Chen-24] Chen KT, Twu SJ, Chang HJ, Lin RS (2003). "Outbreak of Stevens-Johnson Syndrome/Toxic Epidermal Necrolysis Associated with Mebendazole and Metronidazole Use Among Filipino Laborers in Taiwan". American Journal of Public Health 93 (3): 489–492. PMC 1447769. PMID 12604501. edit

[25] Karamanakos, P. N. (2008). "The possibility of serotonin syndrome brought about by the use of metronidazole". Minerva Anestesiologica 74 (11): 679. PMID 18971895. edit

[26] Eisenstein, B. I.; Schaechter, M. (2007). "DNA and Chromosome Mechanics". In Schaechter, M.; Engleberg, N. C.; DiRita, V. J. et al. Schaechter's Mechanisms of Microbial Disease. Hagerstown, MD: Lippincott Williams & Wilkins. p. 28. ISBN 978-0-7817-5342-5. |displayeditors= suggested (help)

[27] Ebel, K.; Koehler, H.; Gamer, A. O.; Jäckh, R. (2005), "Imidazole and Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_661

[28] Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. (2005), "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_173

[29] Kraft, M. Ya.; Kochergin, P. M.; Tsyganova, A. M.; Shlikhunova, V. S. (1989). "Synthesis of metronidazole from ethylenediamine". Pharmaceutical Chemistry Journal 23 (10): 861–863. doi:10.1007/BF00764821.

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