Details of the Drug
General Information of Drug (ID: DMTIVEN)
| Drug Name |
Metronidazole
|
|||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Synonyms |
APMN; Acromona; Anagiardil; Arilin; Atrivyl; Bexon; CONT; Clont; Danizol; Deflamon; Efloran; Elyzol; Entizol; Eumin; Flagemona; Flagesol; Flagil; Flagyl; Flegyl; Florazole; Fossyol; Giatricol; Gineflavir; Giniflavir; Klion; Klont; Meronidal; Methronidazole; Metric; MetroCream; MetroGel; MetroLotion; Metrodzhil; Metrogyl; Metrolag; Metrolyl; Metromidol; Metronidaz; Metronidazol; Metronidazolo; Metronidazolum; Metrotop; Metrozine; Metryl; Mexibol; Monagyl; Monasin; NIDA; Nalox; Nidagel; Noritate; Novonidazol; Orvagil; Protostat; Rathimed; Rosased; Sanatrichom; Satric; Takimetol; Trichazol; Trichex; Trichocide; Trichomol; Trichopal; Trichopol; Tricocet; Tricom; Trikacide; Trikamon; Trikojol; Trikozol; Trimeks; Trivazol; Vagilen; Vagimid; Vandazole; Vertisal; Wagitran; Zadstat; Zidoval; Flagyl Er; Ginefla vir; METRONIDAZOLE USP; Metro Cream; Metro Gel; Metronidazole Monohydrochloride; Metronidazole Phosphoester; Metronidazole in Plastic Container; Metronidazolo [DCIT]; Tricho cordes; Trichomonacid pharmachim; Tricowas B; Bayer 5360; Flagyl 375; M0924; Metric 21; RP 8823; SC 10295; Anabact (TN); Apo-Metronidazole; Deflamon-wirkstoff; Flagyl (TN); IDR-90105; METRO I.V; MetroGel (TN); MetroGel-Vaginal; Metronidazol [INN-Spanish]; Metronidazolum [INN-Latin]; Mexibol (silanes); Neo-Tric; Noritate (TN); RP-8823; Rozex (TN); Tricho-gynaedron; ZERO/004064; CB-01-14 MMX; FLAGYL I.V. RTU IN PLASTIC CONTAINER; Flagyl I.V.; Flagyl I.V. RTU; Metro I.V.; Metro I.V. In Plastic Container; Metrogel-vaginal (TN); Metronidazole (JP15/USP/INN); Metronidazole [USAN:INN:BAN:JAN]; Methyl-5-nitroimidazole-1-ethanol; 1-Hydroxyethyl-2-methyl-5-nitroimidazole; 2-(2-methyl-5-nitroimidazol-1-yl)ethanol; 2-Methyl-5-nitro-1-imidazoleethanol; 2-Methyl-5-nitroimidazole-1-ethanol; MNZ
|
|||||||||||||||||||||||||||
| Indication |
|
|||||||||||||||||||||||||||
| Therapeutic Class |
Antiinfective Agents
|
|||||||||||||||||||||||||||
| Drug Type |
Small molecular drug
|
|||||||||||||||||||||||||||
| Structure |
 |
|||||||||||||||||||||||||||
| 3D MOL | 2D MOL | |||||||||||||||||||||||||||
| #Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 171.15 | ||||||||||||||||||||||||||
| Topological Polar Surface Area (xlogp) | 0 | |||||||||||||||||||||||||||
| Rotatable Bond Count (rotbonds) | 2 | |||||||||||||||||||||||||||
| Hydrogen Bond Donor Count (hbonddonor) | 1 | |||||||||||||||||||||||||||
| Hydrogen Bond Acceptor Count (hbondacc) | 4 | |||||||||||||||||||||||||||
| ADMET Property |
|
|||||||||||||||||||||||||||
| Chemical Identifiers |
|
|||||||||||||||||||||||||||
| Cross-matching ID | ||||||||||||||||||||||||||||
Molecular Interaction Atlas of This Drug
 Drug Therapeutic Target (DTT) |
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
 Drug-Metabolizing Enzyme (DME) |
|
|||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
|
Coadministration of a Drug Treating the Disease Different from Metronidazole (Comorbidity)
|
||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
| 1 | FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018517. | ||||
|---|---|---|---|---|---|
| 2 | ClinicalTrials.gov (NCT00509639) Evaluation of Topical 10% Metronidazole Ointment for the Treatment of Active Perianal Crohn's Disease. U.S. National Institutes of Health. | ||||
| 3 | Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA) | ||||
| 4 | Canadian monograph, Flagyl | ||||
| 5 | BDDCS applied to over 900 drugs | ||||
| 6 | Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches | ||||
| 7 | Lamp KC, Freeman CD, Klutman NE, Lacy MK: Pharmacokinetics and pharmacodynamics of the nitroimidazole antimicrobials. Clin Pharmacokinet. 1999 May;36(5):353-73. doi: 10.2165/00003088-199936050-00004. | ||||
| 8 | Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose | ||||
| 9 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
| 10 | Hernandez Ceruelos A, Romero-Quezada LC, Ruvalcaba Ledezma JC, Lopez Contreras L: Therapeutic uses of metronidazole and its side effects: an update. Eur Rev Med Pharmacol Sci. 2019 Jan;23(1):397-401. doi: 10.26355/eurrev_201901_16788. | ||||
| 11 | DNA breakage due to metronidazole treatment. Mutat Res. 2001 Jul 1;478(1-2):153-8. | ||||
| 12 | Does metronidazole interact with CYP3A substrates by inhibiting their metabolism through this metabolic pathway? Or should other mechanisms be considered? Ann Pharmacother. 2007 Apr;41(4):653-8. | ||||
| 13 | Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. | ||||
| 14 | Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. | ||||
| 15 | The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94. | ||||
| 16 | Mechanism of metronidazole-resistance by isolates of nitroreductase-producing Enterococcus gallinarum and Enterococcus casseliflavus from the human intestinal tract. FEMS Microbiol Lett. 2003 Aug 29;225(2):195-200. | ||||
| 17 | Acetamide--a metabolite of metronidazole formed by the intestinal flora. Biochem Pharmacol. 1979 Dec 15;28(24):3611-5. | ||||
| 18 | Overexpression, isotopic labeling, and spectral characterization of Enterobacter cloacae nitroreductase. Protein Expr Purif. 1998 Jun;13(1):53-60. | ||||
| 19 | Giardia, Entamoeba, and Trichomonas enzymes activate metronidazole (nitroreductases) and inactivate metronidazole (nitroimidazole reductases). Antimicrob Agents Chemother. 2009 Feb;53(2):458-64. | ||||
| 20 | Isolation of metronidazole-resistant Bacteroides fragilis carrying the nimA nitroreductase gene from a patient in Washington State. J Clin Microbiol. 2004 Sep;42(9):4127-9. Case Reports | ||||
| 21 | Biotransformation of 1-nitropyrene in intestinal anaerobic bacteria. Microbiol Immunol. 1982;26(11):993-1005. | ||||
| 22 | Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65. | ||||
| 23 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
| 24 | Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. | ||||
| 25 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
| 26 | Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. | ||||
| 27 | Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98. | ||||
| 28 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
| 29 | The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76. | ||||
| 30 | Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. | ||||
| 31 | Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900. | ||||
| 32 | Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8. | ||||
| 33 | Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731. | ||||
| 34 | UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80. | ||||
| 35 | Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90. | ||||
| 36 | Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36. | ||||
| 37 | Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. | ||||
| 38 | Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4. | ||||
| 39 | Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32. | ||||
| 40 | Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. Drug Metab Dispos. 2007 Aug;35(8):1315-24. | ||||
| 41 | Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. | ||||
| 42 | Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9. | ||||
| 43 | Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101. | ||||
| 44 | Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. | ||||
| 45 | CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15. | ||||
| 46 | Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95. | ||||
| 47 | Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81. | ||||
| 48 | Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72. | ||||
| 49 | Drug Interactions Flockhart Table | ||||
| 50 | Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8. | ||||
| 51 | Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8. | ||||
| 52 | Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94. | ||||
| 53 | Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000. | ||||
| 54 | Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71. | ||||
| 55 | The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. J Steroid Biochem Mol Biol. 1993 Jan;44(1):61-7. | ||||
| 56 | Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66. | ||||
| 57 | Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers. | ||||
| 58 | Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. | ||||
| 59 | Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4. | ||||
| 60 | Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. | ||||
| 61 | Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076. | ||||
| 62 | Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. | ||||
| 63 | New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. | ||||
| 64 | A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7. | ||||
| 65 | A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63. | ||||
| 66 | Isolation of nitrofurantoin-resistant mutants of nitroreductase-producing Clostridium sp. strains from the human intestinal tract. Antimicrob Agents Chemother. 1998 May;42(5):1121-6. | ||||
| 67 | On the nature of the adaptive response induced by mitomycin C in Vibrio cholerae OGAWA 154 cells. Biochem Biophys Res Commun. 1996 Mar 27;220(3):509-14. | ||||
| 68 | The mode of action of clofazimine DNA binding studies. Int J Lepr Other Mycobact Dis. 1976 Jan-Jun;44(1-2):133-4. | ||||
| 69 | Interaction between hydroxystilbamidine and DNA. I. Binding isotherms and thermodynamics of the association. Biochim Biophys Acta. 1975 Sep 12;407(1):24-42. | ||||
| 70 | Interaction of furazolidone with DNA. Biochim Biophys Acta. 1975 Aug 21;402(2):161-5. | ||||
| 71 | Interaction of small molecules with double-stranded RNA: spectroscopic, viscometric, and calorimetric study of hoechst and proflavine binding to PolyCG structures. DNA Cell Biol. 2009 Apr;28(4):209-19. | ||||
| 72 | Clinical pipeline report, company report or official report of MGB Biopharma. | ||||
| 73 | Cerner Multum, Inc. "Australian Product Information.". | ||||
| 74 | Canadian Pharmacists Association. | ||||
| 75 | Giannini AJ, DeFrance DT "Metronidazole and alcohol: potential for combinative abuse." J Toxicol Clin Toxicol 20 (1983): 509-15. [PMID: 6668631] | ||||
| 76 | Dean RP, Talbert RL "Bleeding associated with concurrent warfarin and metronidazole therapy." Drug Intell Clin Pharm 14 (1980): 864-6. | ||||
| 77 | Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ. | ||||
| 78 | Blyden GT, Scavone JM, Greenblatt DJ "Metronidazole impairs clearance of phenytoin but not of alprazolam or lorazepam." J Clin Pharmacol 28 (1988): 240-5. [PMID: 3360972] | ||||
| 79 | Gupte S "Phenobarbital and metabolism of metronidazole." N Engl J Med 308 (1983): 529. [PMID: 6823276] | ||||
| 80 | Product Information. Tindamax (tinidazole). Presutti Laboratories Inc, Arlington Heights, IL. | ||||
| 81 | Carrion C, Espinosa E, Herrero A, Garcia B "Possible vincristine-isoniazid interaction." Ann Pharmacother 29 (1995): 201. [PMID: 7756727] | ||||
| 82 | Argov Z, Mastaglia FL "Drug-induced peripheral neuropathies." Br Med J 1 (1979): 663-6. [PMID: 219931] | ||||
| 83 | Product Information. Zurampic (lesinurad). Astra-Zeneca Pharmaceuticals, Wilmington, DE. | ||||
| 84 | Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA. | ||||
| 85 | Haas CE, Kaufman DC, DiCenzo RC "Effects of metronidazole on hepatic CYP3A4 activity." Pharmacotherapy 21 (2001): 1192-5. [PMID: 11601665] | ||||