Metronidazole citrate disodium

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H13N3O9.2Na
Molecular Weight	389.2259
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of Metronidazole citrate disodium

Structure Search

SMILES

[Na+].[Na+].CC1=NC=C(N1CCOC(=O)CC(O)(CC([O-])=O)C([O-])=O)[N+]([O-])=O

InChI

InChIKey=NOBCCNGXRHLYJA-UHFFFAOYSA-L

InChI=1S/C12H15N3O9.2Na/c1-7-13-6-8(15(22)23)14(7)2-3-24-10(18)5-12(21,11(19)20)4-9(16)17;;/h6,21H,2-5H2,1H3,(H,16,17)(H,19,20);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C12H13N3O9
Molecular Weight	343.2463
Charge	-2
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.emedexpert.com/facts/metronidazole-facts.shtml

Metronidazole was synthesized by France's Rhone-Poulenc laboratories and introduced in the mid-1950s under the brand name Flagel in the US, while Sanofi-Aventis markets metronidazole globally under the same trade name, Flagyl, and also by various generic manufacturers. Metronidazole is one of the rare examples of a drug developed as ant parasitic, which has since gained broad use as an antibacterial agent. Metronidazole, a nitroimidazole, exerts antibacterial effects in an anaerobic environment against most obligate anaerobes. Metronidazole is indicated for the treatment of the following infections due to susceptible strains of sensitive organisms: Trichomoniasis: symptomatic, asymptomatic, asymptomatic consorts; Amebiasis: acute intestinal amebiasis (amebic dysentery) and amebic liver abscess; Anaerobic bacterial infections; Intra-abdominal infections, including peritonitis, intra-abdominal abscess, and liver abscess; Skin and skin structure infections; Gynecologic infections, including endometritis, endomyometritis, tubo-ovarian abscess, and postsurgical vaginal cuff infection; Bacterial septicemia; Bone and joint infections, as adjunctive therapy; Central Nervous System infections, including meningitis and brain abscess; Lower Respiratory Tract infections, including pneumonia, empyema, and lung abscess; Endocarditis. Metronidazole is NOT effective for infections caused by aerobic bacteria that can survive in the presence of oxygen. Metronidazole is only effective against anaerobic bacterial infections because the presence of oxygen will inhibit the nitrogen-reduction process that is crucial to the drug's mechanism of action. Once metronidazole enters the organism by passive diffusion and activated in the cytoplasm of susceptible anaerobic bacteria, it is reduced; this process includes intracellular electron transport proteins such as ferredoxin, transfer of an electron to the nitro group of the metronidazole, and formation of a short-lived nitroso free radical. Because of this alteration of the metronidazole molecule, a concentration gradient is created and maintained which promotes the drug’s intracellular transport. The reduced form of metronidazole and free radicals can interact with DNA leading to inhibition of DNA synthesis and DNA degradation leading to death of the bacteria. The precise mechanism of action of metronidazole is unknown. Metronidazole has a limited spectrum of activity that encompasses various protozoans and most Gram-negative and Gram-positive anaerobic bacteria. Metronidazole has activity against protozoans like Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis, for which the drug was first approved as an effective treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2364041 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Curative	Approved 8583	FLAGYL Approved Use INDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date 1963
Acute intestinal amebiasis 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Curative	Approved 8583	FLAGYL Approved Use INDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date 1963
Anaerobic bacterial infections 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Curative	Approved 8583	FLAGYL Approved Use INDICATIONS & USAGE Metronidazole vaginal gel USP, 0.75% is indicated in the treatment of bacterial vaginosis (formerly referred to as Haemophilus vaginitis, Gardnerella vaginitis, nonspecific vaginitis, Corynebacterium vaginitis, or anaerobic vaginosis). NOTE: For purposes of this indication, a clinical diagnosis of bacterial vaginosis is usually defined by the presence of a homogeneous vaginal discharge that (a) has a pH of greater than 4.5, (b) emits a “fishy” amine odor when mixed with a 10% KOH solution, and (c) contains clue cells on microscopic examination. Gram’s stain results consistent with a diagnosis of bacterial vaginosis include (a) markedly reduced or absent Lactobacillus morphology, (b) predominance of Gardnerella morphotype, and (c) absent or few white blood cells. Other pathogens commonly associated with vulvovaginitis, e.g., Trichomonas vaginalis, Chlamydia trachomatis, N. gonorrhoeae, Candida albicans, and Herpes simplex virus should be ruled out. Launch Date 1963

C_max

Value	Dose	Analyte	Population
16.54 mg/L Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01222585	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: intravenous experiment type: single co-administered:	METRONIDAZOLE plasma	Homo sapiens population: unhealthy age: CHILD sex: UNKNOWN food status: UNKNOWN
6.77 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
12 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
40 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
25 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018890s052lbl.pdf	7.5 mg/kg 4 times / day steady-state, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
75.23 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
7.76 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22918856	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/12623slr059_flagyl_lbl.pdf	2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered:	METRONIDAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018890s052lbl.pdf	unknown, oral	METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018890s052lbl.pdf	unknown, oral		METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/7717611/	unhealthy, 58 years Health Status: unhealthy Age Group: 58 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7717611/	Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (9.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/7717611/
8.5 g single, oral Overdose Dose: 8.5 g Route: oral Route: single Dose: 8.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/15956228/	unhealthy, 62 years Health Status: unhealthy Age Group: 62 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15956228/	Sources: https://pubmed.ncbi.nlm.nih.gov/15956228/
1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/348320/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/348320/	DLT: Nausea and vomiting, Generalised onset motor seizure... Dose limiting toxicities: Nausea and vomiting (13.5%) Generalised onset motor seizure (12.8%) Neurotoxicity NOS (10.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/348320/
5.3 mg/m2 3 times / week multiple, oral Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	DLT: Gastrointestinal toxicity, Central nervous system toxicity... Dose limiting toxicities: Gastrointestinal toxicity (14.5%) Central nervous system toxicity (13.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/
1350 mg 3 times / day steady, oral Overdose Dose: 1350 mg, 3 times / day Route: oral Route: steady Dose: 1350 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9195118/	unhealthy, preterm newborn Health Status: unhealthy Age Group: preterm newborn Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9195118/	Sources: https://pubmed.ncbi.nlm.nih.gov/9195118/

AEs

AE	Significance	Dose	Population
Hepatotoxicity	9.6% Disc. AE	12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/7717611/	unhealthy, 58 years Health Status: unhealthy Age Group: 58 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7717611/
Neurotoxicity NOS	10.9% DLT	1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/348320/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/348320/
Generalised onset motor seizure	12.8% DLT	1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/348320/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/348320/
Nausea and vomiting	13.5% DLT	1000 mg/m2 3 times / day steady, oral Highest studied dose Dose: 1000 mg/m2, 3 times / day Route: oral Route: steady Dose: 1000 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/348320/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/348320/
Central nervous system toxicity	13.7% DLT	5.3 mg/m2 3 times / week multiple, oral Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/
Gastrointestinal toxicity	14.5% DLT	5.3 mg/m2 3 times / week multiple, oral Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 supressor 22	supressor 19 inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 OAT1 725 OAT2 153 OAT3 747 OAT4 150 OATP1A2 43 OATP1B1 1079 OATP1B3 961 OATP2B1 157 OCT1 620 OCT2 779 OCT3 159

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s002280000201 Page: -	no
OAT2 155	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP1A2 43	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP2B1 162	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OCT1 656	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OCT3 161	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C19 2141	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C19 2141	supressor 160 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2C8 1117	supressor 160 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2C9 2497	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C9 2497	supressor 160 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2D6 2546	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP3A4 2633	supressor 160 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
OAT1 730	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OAT3 749	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OAT4 150	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OATP1B3 970	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OCT2 782	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6909	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6909
ChemicalBook	CB5248430	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5248430
eMolecules	511411	https://www.emolecules.com/cgi-bin/more?vid=511411
MolPort	MolPort-000-141-892	https://www.molport.com/shop/molecule-link/MolPort-000-141-892
Selleck Chemicals	Metronidazole(Flagyl)	http://www.selleckchem.com/products/Metronidazole(Flagyl).html
ZINC	ZINC000000113442	http://zinc15.docking.org/substances/ZINC000000113442

PubMed

Title	Date	PubMed
The effect of therapeutic drugs used in inflammatory bowel disease on the incidence and growth of colonic cancer in the dimethylhydrazine rat model.	1992 Nov	1358165
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Antituberculosis activity of certain antifungal and antihelmintic drugs.	1999	10707260
Metronidazole ototoxicity--report of two cases.	1999 Apr	10474673
Metronidazole therapy in mice infected with tuberculosis.	1999 May	10223954
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands.	1999 Sep	10484002
Do ethanol and metronidazole interact to produce a disulfiram-like reaction?	2000 Feb	10676835
Mesalamine-induced chest pain: a case report.	2000 May	10833545
Convulsions induced by metronidazole treatment for Clostridium difficile-associated disease in chronic renal failure.	2000 May	10830559
A simple, efficient and inexpensive program for preventing prematurity.	2001	11447924
[Pneumatosis cystoides intestinalis: the first case in Congo].	2001 Apr-Jun	11440892
Technology evaluation: CEA-TRICOM, Therion Biologics Corp.	2001 Aug	11525565
[Diagnostic, therapeutic and prognostic aspects of intestinal typhoid perforations in children of Abidjan, Côte d'Ivoire].	2001 Dec	11889935
[A comparative study on wound healing treated by different doses of bovine basic fibroblast growth factor (bFGF)].	2001 Feb	11876901
Vector-driven hyperexpression of a triad of costimulatory molecules confers enhanced T-cell stimulatory capacity to DC precursors.	2001 Jul-Aug	11418301
Enhancing the potency of peptide-pulsed antigen presenting cells by vector-driven hyperexpression of a triad of costimulatory molecules.	2001 May 14	11348723
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Metronidazole-induced encephalopathy in a uremic patient: a case report.	2001 Sep	11528241
[The efficacy of the Helicobacter pylori eradication in people of an advanced age].	2002	12183983
Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase.	2002 Apr 11	11931611
Role of P53 functionality in the genotoxicity of metronidazole and its hydroxy metabolite.	2002 Apr 25	11934438
Allergic contact dermatitis from 2-bromo-2-nitropropane-1,3-diol in Metrogel.	2002 Jan	11918595
Metronidazol as a probable cause of severe liver injury.	2002 Jan-Feb	11941968
Lack of disulfiram-like reaction with metronidazole and ethanol.	2002 Jun	12022894
Effectiveness of metronidazole gel on cyclosporine-induced gingival overgrowth in heart transplant patients.	2002 Mar	11996160
[Microbiologic characteristics of wound infectious process in use of ion-exchange sorbents].	2003	14671544
[Anaerobic bacteria in bronchoalveolar lavage fluid (BAL) after thoracic surgery].	2003	14577197
An unexpected and severe neurological disorder with permanent disability acquired during short-course treatment with metronidazole.	2003	12839161
An open label crossover trial of effects of metronidazol on hyperlipidaemia.	2003 Aug	12957743
Renal papillary necrosis induced by naproxen.	2003 Aug	12774222
Metronidazole-induced encephalopathy and inferior olivary hypertrophy: lesion analysis with diffusion-weighted imaging and apparent diffusion coefficient maps.	2003 Dec	14676060
Solvent effects in permeation assessed in vivo by skin surface biopsy.	2003 Dec 18	14680512
[Vulvar amebiasis. Report of a case and review of the literature].	2003 Feb	12708354
A triad of costimulatory molecules synergize to amplify T-cell activation in both vector-based and vector-infected dendritic cell vaccines.	2003 May	12751840
A comparison of 15% azelaic acid gel and 0.75% metronidazole gel in the topical treatment of papulopustular rosacea: results of a randomized trial.	2003 Nov	14623704
Modified vaccinia virus ankara recombinants are as potent as vaccinia recombinants in diversified prime and boost vaccine regimens to elicit therapeutic antitumor responses.	2003 Nov 15	14633725
Ruthenium(II) sulfoxide-maltolato and -nitroimidazole complexes: synthesis and MTT assay.	2003 Nov 17	14606854
Bronchospasm and laryngeal stridor as an adverse effect of oxytocin treatment.	2003 Oct	12974972
Cardiac diphtheria in a previously immunized individual.	2003 Sep	14527057
MR imaging and diffusion-weighted imaging changes in metronidazole (Flagyl)-induced cerebellar toxicity.	2003 Sep	13679281
Crohn's disease--when to operate?	2004	15771291
Reduced stem cell mobilization in mice receiving antibiotic modulation of the intestinal flora: involvement of endotoxins as cofactors in mobilization.	2004 Jan 1	12969972
A case of clarithromycin-induced manic episode (antibiomania).	2004 Mar	14731313

Patents

Sample Use Guides

In Vivo Use Guide

Trichomoniasis: In the Female: One-day treatment − two grams of FLAGYL, given ither as a single dose or in two divided doses of one gram each, given in the same day. Anaerobic Bacterial Infections: In the treatment of most serious anaerobic infections, intravenous metronidazole is usually administered initially. The usual adult oral dosage is 7.5 mg/kg every six hours (approx. 500 mg for a 70-kg adult). A maximum of 4 g should not be exceeded during a 24-hour period. Amebiasis: Adults: For acute intestinal amebiasis (acute amebic dysentery): 750 mg orally three times daily for 5 to 10 days. For amebic liver abscess: 500 mg or 750 mg orally three times daily for 5 to 10 days. Pediatric patients: 35 to 50 mg/kg/24 hours, divided into three doses, orally for 10 days.

Route of Administration: Other

In Vitro Use Guide

Cells incubated with lethal drug (Metronidazole (MTZ)) concentration exhibit unchanged DNA profile, only about 50% of cells are positive for γH2A and lose an ability to attach to a surface after few hours of incubation. It is likely that the early reaction of cells to lethal concentration of MTZ is not primarily initiated by the reaction to DNA damage but rather by the immediate interaction of MTZ with biomolecules where activated MTZ is generated.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 12:03:00 GMT 2025` Edited by `admin` on `Wed Apr 02 12:03:00 GMT 2025`
Record UNII	8LKQ4FU9YN
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Name

Type

Language

Metronidazole citrate disodium

Common Name

English

Disodium metronidazole citrate

Preferred Name

English

disodium 2-hydroxy-2-[2-[2-(2-methyl-5-nitro-imidazol-1-yl)ethoxy]-2-oxo-ethyl]butanedioate

Systematic Name

English

Code System Code Type Description

PUBCHEM

165412101

Created by admin on Wed Apr 02 12:03:00 GMT 2025 , Edited by admin on Wed Apr 02 12:03:00 GMT 2025

PRIMARY

FDA UNII

8LKQ4FU9YN

Created by admin on Wed Apr 02 12:03:00 GMT 2025 , Edited by admin on Wed Apr 02 12:03:00 GMT 2025

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Related Record Type Details


					8Y356BW999

metronidazole citrate

PARENT -> SALT/SOLVATE

Amount:

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdfCurator's Comment: description was created based on several sources, including http://www.emedexpert.com/facts/metronidazole-facts.shtml

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.emedexpert.com/facts/metronidazole-facts.shtml

C_max

T_1/2

F_unbound

Drug as perpetrator