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M3761 Sigma-Aldrich

Metronidazole

analytical standard

Synonym: 2-Methyl-5-nitroimidazole-1-ethanol

  • CAS Number 443-48-1

  • Empirical Formula (Hill Notation) C6H9N3O3

  • Molecular Weight 171.15

  •  Beilstein Registry Number 611683

  •  EC Number 207-136-1

  •  MDL number MFCD00009750

  •  PubChem Substance ID 24896871

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References

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Guidelines for diagnosis, treatment, and prevention of Clostridium difficile infections. Surawicz CM, Brandt LJ, Binion DG, et al. Am. J. Gastroenterol. 108(4), 478-98; quiz 499, (2013)

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Metronidazole is still the drug of choice for treatment of anaerobic infections. Löfmark S, Edlund C, and Nord CE Clin. Infect. Dis. 50 Suppl 1, S16-23, (2010)

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The clinical effect of scaling and root planing and the concomitant administration of systemic amoxicillin and metronidazole: a systematic review. Zandbergen D, Slot DE, Cobb CM, et al. J. Periodontol. 84(3), 332-51, (2013)

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Blastocystis ratti contains cysteine proteases that mediate interleukin-8 response from human intestinal epithelial cells in an NF-kappaB-dependent manner. Manoj K. Puthia et al Eukaryotic Cell 7, 435-43, (2008)

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Follow-up of Helicobacter pylori infection in children over two decades (1988-2007): persistence, relapse and acquisition rates. Vanderpas J, Bontems P, Miendje Deyi VY, et al. Epidemiol. Infect. 142(4), 767-75, (2014)

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Antibiotic prophylaxis for hysterectomy, a prospective cohort study: cefuroxime, metronidazole, or both? Brummer TH, Heikkinen AM, Jalkanen J, et al. BJOG 120(10), 1269-76, (2013)

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Treatment failure and recurrence of Clostridium difficile infection following treatment with vancomycin or metronidazole: a systematic review of the evidence. Vardakas KZ, Polyzos KA, Patouni K, et al. Int. J. Antimicrob. Agents 40(1), 1-8, (2012)

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Ebola in Freetown area, Sierra Leone--a case study of 581 patients. Ansumana R, Jacobsen KH, Sahr F, et al. N. Engl. J. Med. 372(6), 587-8, (2015)

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Single-dose compared with multiple day antibiotic prophylaxis for cesarean section in low-resource settings, a randomized controlled, noninferiority trial. Westen EH, Kolk PR, van Velzen CL, et al. Acta Obstet. Gynecol. Scand. 94(1), 43-9, (2015)

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Helicobacter pylori first-line and rescue treatments in the presence of penicillin allergy. Gisbert JP, Barrio J, Modolell I, et al. Dig. Dis. Sci. 60(2), 458-64, (2015)

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Dientamoeba fragilis and chronic abdominal pain in children: a case-control study. de Jong MJ, Korterink JJ, Benninga MA, et al. Arch. Dis. Child. 99(12), 1109-13, (2014)

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Metronidazole-induced encephalopathy: an uncommon scenario. Chakrabarti S and Pan K N. Z. Med. J. 127(1393), 120-2, (2014)

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In vitro evaluation of extemporaneously compounded immediate-release capsules with premixed excipients, based on the biopharmaceutics classification system (BCS) of the drugs. Pinheiro VA, Danopoulos P, Demirdjian L, et al. Int. J. Pharm. Compd. 17(5), 424-31, (2013)

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Use of topical metronidazole in the treatment of anorectal Crohn's disease. McElhiney LF Int. J. Pharm. Compd. 17(5), 380-3, (2013)

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Nonsurgical treatment of aggressive periodontitis with photodynamic therapy or systemic antibiotics. Three-month results of a randomized, prospective, controlled clinical study. Arweiler NB, Pietruska M, Skurska A, et al. Schweiz. Monatsschr. Zahnmed. 123(6), 532-44, (2013)

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[A case of pulmonary tuberculosis in which diagnosis was delayed because of prior treatment with fluoroquinolone and metronidazole]. Morioka S, Ema R, Sakurai A, et al. Kekkaku 88(3), 305-9, (2013)

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[Clostridium difficile infections - still a major challenge]. Strauss R and Neurath MF MMW Fortschr. Med. 155(7), 57-9, (2013)

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Bismuth + metronidazole + tetracycline. Why risk adding bismuth? Prescrire Int. 22(137), 89-92, (2013)

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[Chlamydial infection with marked ascites that simulated ovarian cancer]. Ugianskiene A Ugeskr. Laeg. 175(14), 963-5, (2013)

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[Acute cholecystitis]. Füessl HS MMW Fortschr. Med. 155(1), 49, (2013)

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Gingival pain: an unusual side effect of ziprasidone. Raghunath A BMJ Case Rep. 2013, doi:10.1136/bcr-2012-007577, (2013)

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Amoxicillin/metronidazole or scaling and root planing in the treatment of chronic periodontitis. Bono A and Brunotto M Acta Odontol. Latinoam. 23(3), 196-203, (2010)

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[Pancreatitis associated with metronidazole]. Romero Ganuza FJ Gastroenterol. Hepatol. 31(4), 264-5, (2008)

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Bioactive nanofibrous scaffolds for regenerative endodontics. Bottino MC, Kamocki K, Yassen GH, et al. J. Dent. Res. 92(11), 963-9, (2013)

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A new strategy for the prevention of Clostridium difficile infection. Howerton A, Patra M, and Abel-Santos E J. Infect. Dis. 207(10), 1498-504, (2013)

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Effectiveness of systemic amoxicillin/metronidazole as an adjunctive therapy to full-mouth scaling and root planing in the treatment of aggressive periodontitis: a systematic review and meta-analysis. Sgolastra F, Petrucci A, Gatto R, et al. J. Periodontol. 83(6), 731-43, (2012)

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Effectiveness of systemic amoxicillin/metronidazole as adjunctive therapy to scaling and root planing in the treatment of chronic periodontitis: a systematic review and meta-analysis. Sgolastra F, Gatto R, Petrucci A, et al. J. Periodontol. 83(10), 1257-69, (2012)

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Prolonged impact of antibiotics on intestinal microbial ecology and susceptibility to enteric Salmonella infection. A. Croswell, et al., Infect. Immun. 77, 2741-2753, (2009)

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Eradication of Helicobacter pylori according to 23S ribosomal RNA point mutations associated with clarithromycin resistance. Lee HJ, Kim JI, Cheung DY, et al. J. Infect. Dis. 208(7), 1123-30, (2013)

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Nonoperative management of perforated diverticulitis with extraluminal air is safe and effective in selected patients. Sallinen VJ, Mentula PJ, and Leppäniemi AK Dis. Colon Rectum 57(7), 875-81, (2014)

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Polymersome-mediated intracellular delivery of antibiotics to treat Porphyromonas gingivalis-infected oral epithelial cells. Wayakanon K, Thornhill MH, Douglas CW, et al. FASEB J. 27(11), 4455-65, (2013)

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Revascularization/Regeneration performed in immature molars: case reports. Sönmez IS, Akbay Oba A, and Erkmen Almaz M J. Clin. Pediatr. Dent. 37(3), 231-4, (2013)

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LPS-induced inflammatory response after therapy of aggressive periodontitis. Shaddox LM, Gonçalves PF, Vovk A, et al. J. Dent. Res. 92(8), 702-8, (2013)

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Image-guided percutaneous procedure plus metronidazole versus metronidazole alone for uncomplicated amoebic liver abscess. Chavez-Tapia NC, Hernandez-Calleros J, Tellez-Avila FI, et al. Cochrane Database Syst. Rev. (1), CD004886, (2009)

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DNase inhibits Gardnerella vaginalis biofilms in vitro and in vivo. Hymes SR, Randis TM, Sun TY, et al. J. Infect. Dis. 207(10), 1491-7, (2013)

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Cord colitis syndrome: a cause of granulomatous inflammation in the upper and lower gastrointestinal tract. Gupta NK and Masia R Am. J. Surg. Pathol. 37(7), 1109-13, (2013)

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Antibiotic treatment of pregnant non-obese diabetic mice leads to altered gut microbiota and intestinal immunological changes in the offspring. Tormo-Badia N, Håkansson Å, Vasudevan K, et al. Scand. J. Immunol. 80(4), 250-60, (2014)

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The effects of statins on the clinical outcomes of Clostridium difficile infection in hospitalised patients. Park SW, Choi AR, Lee HJ, et al. Aliment. Pharmacol. Ther. 38(6), 619-27, (2013)

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Drug library screening against metronidazole-sensitive and metronidazole-resistant Trichomonas vaginalis isolates. Goodhew EB and Secor WE Sex. Transm. Infect. 89(6), 479-84, (2013)

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Metronidazole-induced central nervous system toxicity: a systematic review. Kuriyama A, Jackson JL, Doi A, et al. Clin. Neuropharmacol. 34(6), 241-7, (2011)

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In vitro activity of pyrvinium pamoate against Entamoeba histolytica and Giardia intestinalis using radiolabelled thymidine incorporation and an SYBR Green I-based fluorescence assay. Downey AS J. Antimicrob. Chemother. 64(4), 751-4, (2009)

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Structural basis for inactivation of Giardia lamblia carbamate kinase by disulfiram. Galkin A, Kulakova L, Lim K, et al. J. Biol. Chem. 289(15), 10502-9, (2014)

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[Antimicrobial therapy of Clostridium difficile infection. Systematic review and meta-analysis of the scientific evidence]. Brodszky V, Gulácsi L, Ludwig E, et al. Orv. Hetil. 154(23), 890-9, (2013)

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Cetuximab-induced skin exanthema: prophylactic and reactive skin therapy are equally effective. Wehler TC, Graf C, Möhler M, et al. J. Cancer Res. Clin. Oncol. 139(10), 1667-72, (2013)

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Clinical manifestations and risk factors of amebic liver abscess in Southeast Taiwan compared with other regions of Taiwan. Chen HL, Bair MJ, Lin IT, et al. Am. J. Trop. Med. Hyg. 89(6), 1214-8, (2013)

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An integrated microfludic device for culturing and screening of Giardia lamblia. Zheng GX, Zhang XM, Yang YS, et al. Exp. Parasitol. 137, 1-7, (2014)

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Preoperative oral antibiotics and intravenous antimicrobial prophylaxis reduce the incidence of surgical site infections in patients with ulcerative colitis undergoing IPAA. Oshima T, Takesue Y, Ikeuchi H, et al. Dis. Colon Rectum 56(10), 1149-55, (2013)

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Treatment of metronidazole-refractory Clostridium difficile enteritis with vancomycin. Follmar KE, Condron SA, Turner II, et al. Surg. Infect. (Larchmt.) 9(2), 195-200, (2008)

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Statin use and infections in Veterans with cirrhosis. Motzkus-Feagans C, Pakyz AL, Ratliff SM, et al. Aliment. Pharmacol. Ther. 38(6), 611-8, (2013)

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Evaluation of antitumor activity and development of solid lipid nanoparticles of metronidazole analogue. Lages EB, de Freitas MB, Gonçalves IM, et al. J. Biomed. Nanotechnol. 9(11), 1939-44, (2013)

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Assessment of treatment patterns and patient outcomes before vs after implementation of a severity-based Clostridium difficile infection treatment policy. Jardin CG, Palmer HR, Shah DN, et al. J. Hosp. Infect. 85(1), 28-32, (2013)

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Metronidazole-induced Encephalopathy: Case Report and Review Literature. Huang YT, Chen LA, and Cheng SJ Acta Neurol. Taiwan. 21(2), 74-8, (2012)

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The early use of appropriate prophylactic antibiotics in susceptible women for the prevention of preterm birth of infectious etiology. Joergensen JS, Kjær Weile LK, and Lamont RF Expert Opin. Pharmacother. 15(15), 2173-91, (2014)

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Anti-Helicobacter pylori and urease inhibition activities of some traditional medicinal plants. Amin M, Anwar F, Naz F, et al. Molecules 18(2), 2135-49, (2013)

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PAMAM dendrimer generation 5-pluronic F127 nanofilm as a matrix for local metronidazole release. Dung TH, Do le T, and Yoo H J. Biomed. Nanotechnol. 9(7), 1286-92, (2013)

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The role of phenoxymethylpenicillin, amoxicillin, metronidazole and clindamycin in the management of acute dentoalveolar abscesses--a review. Ellison SJ Br. Dent. J. 206(7), 357-62, (2009)

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Role of oral corticosteroids in orbital cellulitis. Pushker N, Tejwani LK, Bajaj MS, et al. Am. J. Ophthalmol. 156(1), 178-183.e1, (2013)

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Cerebellar ataxia following prolonged use of metronidazole: case report and literature review. Patel K, Green-Hopkins I, Lu S, et al. Int. J. Infect. Dis. 12(6), e111-4, (2008)

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A selective antibiotic prophylaxis policy for laparoscopic cholecystectomy is effective in minimising infective complications. Yanni F, Mekhail P, and Morris-Stiff G Ann. R. Coll. Surg. Engl. 95(5), 345-8, (2013)

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Metronidazole-induced encephalopathy: a case report and review of the literature. Bottenberg MM, Hegge KA, Eastman DK, et al. J. Clin. Pharmacol. 51(1), 112-6, (2011)

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A rare adverse effect of metronidazole: nervous system symptoms. Kafadar I, Moustafa F, Yalçın K, et al. Pediatr. Emerg. Care 29(6), 751-2, (2013)

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Antibiotic resistance of Helicobacter pylori in Mashhad, Iran. Zendedel A, Moradimoghadam F, Almasi V, et al. J. Pak. Med. Assoc. 63(3), 336-9, (2013)

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Innovative use of topical metronidazole. Zip CM Dermatol. Clin. 28(3), 525-34, (2010)

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Kinetic spectrophotometric H-point standard addition method for the simultaneous determination of diloxanide furoate and metronidazole in binary mixtures and biological fluids. Issa MM, Nejem RM, Abu Shanab AM, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 114, 592-8, (2013)

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Comparison of treatment outcomes with vancomycin alone versus combination therapy in severe Clostridium difficile infection. Bass SN, Bauer SR, Neuner EA, et al. J. Hosp. Infect. 85(1), 22-7, (2013)

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The role of antimicrobials in Crohn's disease. Kale-Pradhan PB, Zhao JJ, Palmer JR, et al. Expert Rev. Gastroenterol. Hepatol. 7(3), 281-8, (2013)

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Vesicular powder as carrier for doxycycline hydrochloride and metronidazole combination therapy. Gad HA, Kamel AO, Sammour OA, et al. Pharm. Dev. Technol. 19(6), 755-68, (2014)

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Scuticociliatid ciliate outbreak in Australian potbellied seahorse, Hippocampus abdominalis (Lesson, 1827): clinical signs, histopathologic findings, and treatment with metronidazole. Di Cicco E, Paradis E, Stephen C, et al. J. Zoo Wildl. Med. 44(2), 435-40, (2013)

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Might Helicobacter pylori infection be associated with distortion on taste perception? Cecchini MP, Pellegrini C, Bassetto MA, et al. Med. Hypotheses 81(3), 496-9, (2013)

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Effects of radiation and vitamin C treatment on metronidazole genotoxicity in mice. Das Roy L, Giri S, Singh S, et al. Mutat. Res. 753(2), 65-71, (2013)

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Establishment of a new murine model of liver abscess induced by Fusobacterium necrophorum injected into the caudal vein. Nagaoka K, Yanagihara K, Harada Y, et al. J. Med. Microbiol. 62(Pt 11), 1755-9, (2013)

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Prevention and control of sexually transmissible infections among hotel-based female sex workers in Dhaka, Bangladesh. McCormick DF, Rahman M, Zadrozny S, et al. Sex. Health 10(6), 478-86, (2013)

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False-negative serologies in amebic liver abscess: report of two cases. Otto MP, Gérôme P, Rapp C, et al. J. Travel Med. 20(2), 131-3, (2013)

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What would we do without metronidazole? Stover KR, Riche DM, Gandy CL, et al. Am. J. Med. Sci. 343(4), 316-9, (2012)

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Chromatographic methods for simultaneous determination of diiodohydroxyquinoline and metronidazole in their binary mixture. Ali NW, Gamal M, and Abdelkawy M Pak. J. Pharm. Sci. 26(5), 865-71, (2013)

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A simple reagent-free spectrophotometric assay for monitoring metronidazole therapy in aquarium water. Webb DH, Marrero C, Ellis H, et al. J. Aquat. Anim. Health 25(3), 165-70, (2013)

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Metronidazole and the immune system. Shakir L, Javeed A, Ashraf M, et al. Pharmazie 66(6), 393-8, (2011)

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Fever of unknown origin attributable to haematocolpos infected with Salmonella enterica Serotypetyphi resistant to nalidixic acid: a case report. Saxena S, Dwivedi M, Batra P, et al. J. Health. Popul. Nutr. 31(3), 403-4, (2013)

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[Tetracyclines, sulfonamides, and metronidazole]. Vicente D and Pérez-Trallero E Enferm. Infecc. Microbiol. Clin. 28(2), 122-30, (2010)

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Trichomonas vaginalis: an audit of clinical practice and the demography of infected patients at three London genitourinary medicine clinics. Tittle V, Bull L, and Boag F Int. J. STD AIDS 24(11), 902-4, (2013)

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Presentation, distribution pattern, and management of diverticular disease in a Nigerian tertiary hospital. Alatise OI, Arigbabu AO, Lawal OO, et al. Niger. J. Clin. Pract. 16(2), 226-31, (2013)

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Purity determination of gynalgin bactericidal tablets with HPLC method. Białecka W, Kulik A, Podolska M, et al. Acta Pol. Pharm. 70(1), 51-8, (2013)

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Vancomycin-associated neutrophilic dermatitis histologically mimicking Cryptococcus. Boyd AS and Ortleb M J. Am. Acad. Dermatol. 70(4), e86-8, (2014)

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Patterns of ambulatory care usage and leading treatments for rosacea. Davis SA and Feldman SR J. Dermatolog. Treat. 25(4), 275-7, (2014)

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Magnetic resonance imaging of metronidazole induced encephalopathy. Naqi R, Azeemuddin M, and Beg MA J. Pak. Med. Assoc. 62(8), 843-4, (2012)

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Pneumocephalus as uncommon presentation of pneumococcal meningitis. Rota E, Sacchini D, Paolillo F, et al. Neurol. India 61(3), 314-5, (2013)

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Paracetamol or metronidazole? Loader J and Brooks T Br. J. Anaesth. 111(2), 301-2, (2013)

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Granulomatous lymphangitis. Vricella GJ, Coplen DE, Austin PF, et al. J. Urol. 190(3), 1052-3, (2013)

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Brain MRI evolution of metronidazole intoxication. Erdener SE, Kansu T, Arsava EM, et al. Neurology 80(19), 1816-7, (2013)

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Commentary: vancomycin or metronidazole in patients with primary sclerosing cholangitis? Paterson JC and Dillon JF Aliment. Pharmacol. Ther. 37(9), 915, (2013)

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[Is sequential eradication of Helicobacter pylori effective? Sequential treatment more effective than triple therapy in patients with clarithromycin resistance]. Malfertheiner P Dtsch. Med. Wochenschr. 138(13), 628, (2013)

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Metronidazole-induced encephalopathy: case report and review of MRI findings. Desai JA, Dobson J, Melanson M, et al. Can J Neurol Sci 38(3), 512-3, (2011)

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Merck 14,6157

Beil. 23,V,5,63

Aldrich MSDS 1, 1325:C / Corp MSDS 1 (2), 2467:A / FT-IR 2 (3), 3515:A / FT-IR 1 (2), 619:B / FT-NMR 1 (3), 84:B / NMR-Reference 2 (2), 490:C / RegBook 1 (2), 2359:G / Sax 6, 1887 / Sigma FT-IR 1 (2), 757:D / Structure Index 1, 373:D:5

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