METRONIDAZOLE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H9N3O3.ClH
Molecular Weight	207.615
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of METRONIDAZOLE HYDROCHLORIDE

Structure Search

SMILES

Cl.CC1=NC=C(N1CCO)[N+]([O-])=O

InChI

InChIKey=FPTPAIQTXYFGJC-UHFFFAOYSA-N

InChI=1S/C6H9N3O3.ClH/c1-5-7-4-6(9(11)12)8(5)2-3-10;/h4,10H,2-3H2,1H3;1H

HIDE SMILES / InChI

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 278 Target ID: CHEMBL2364041 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Trichomoniasis 18 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Curative	Approved 8429	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 8429	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 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/012623s066lbl.pdf	Curative	Approved 8429	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
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
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
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
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
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
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: ∞ants sex: food status:

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
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/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/2018/018890s052lbl.pdf	unknown, oral	METRONIDAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
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

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 n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: extensive past medical history, including end-stage renal disease Age Group: 62 years Sex: M Population Size: 1 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 n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 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 (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 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 n = 1 Health Status: unhealthy Condition: bloody stools and apnoea Age Group: preterm newborn Sex: F Population Size: 1 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 n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 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 n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 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 n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 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 n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/348320/
Central nervous system toxicity	13.7% DLT	5.3 mg/m2 3 times / week multiple, oral (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/
Gastrointestinal toxicity	14.5% DLT	5.3 mg/m2 3 times / week multiple, oral (mean) Highest studied dose Dose: 5.3 mg/m2, 3 times / week Route: oral Route: multiple Dose: 5.3 mg/m2, 3 times / week Co-administed with:: radiotherapy Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/	unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: https://pubmed.ncbi.nlm.nih.gov/6849198/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 supressor 21	supressor 19 inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 OAT1 599 OAT2 145 OAT3 642 OAT4 146 OATP1A2 35 OATP1B1 788 OATP1B3 706 OATP2B1 123 OCT1 512 OCT2 647 OCT3 150

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://link.springer.com/article/10.1007/s002280000201 Page: -	no
OAT2 147	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP1A2 35	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP1B1 803	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OATP2B1 126	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OCT1 543	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
OCT3 150	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C19 1553	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C19 1553	supressor 155 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2C8 965	supressor 155 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2C9 1819	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP2C9 1819	supressor 155 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
CYP2D6 1891	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529190650T Page: -	yes
CYP3A4 1925	supressor 155 Sources: https://www.tandfonline.com/doi/pdf/10.3109/00498254.2014.990948?needAccess=true Page: -	yes
OAT1 603	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OAT3 644	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OAT4 146	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OATP1B3 715	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S0928098718300022 Page: -	yes
OCT2 648	inhibitor 3277 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
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
eMolecules	511411	https://www.emolecules.com/cgi-bin/more?vid=511411

PubMed

Title	Date	PubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Acute encephalopathy associated with metronidazole therapy.	1997 Mar-Jun	10895243
Do ethanol and metronidazole interact to produce a disulfiram-like reaction?	2000 Feb	10676835
A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis.	2000 Jun 22	10879539
Mesalamine-induced chest pain: a case report.	2000 May	10833545
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
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.	2001 Jun 15	11377375
Metronidazole-induced encephalopathy in a uremic patient: a case report.	2001 Sep	11528241
Validation of a method for the detection and confirmation of nitroimidazoles and corresponding hydroxy metabolites in turkey and swine muscle by means of gas chromatography-negative ion chemical ionization mass spectrometry.	2001 Sep 15	11585131
[The efficacy of the Helicobacter pylori eradication in people of an advanced age].	2002	12183983
Role of P53 functionality in the genotoxicity of metronidazole and its hydroxy metabolite.	2002 Apr 25	11934438
Vaccine-based therapy directed against carcinoembryonic antigen demonstrates antitumor activity on spontaneous intestinal tumors in the absence of autoimmunity.	2002 Dec 1	12460911
[Fever and weight loss as leading symptoms of infection with giardia lamblia].	2002 Feb	11857101
Antimicrobial-induced mania (antibiomania): a review of spontaneous reports.	2002 Feb	11799346
Metronidazol as a probable cause of severe liver injury.	2002 Jan-Feb	11941968
Local antimicrobial therapy after initial periodontal treatment.	2002 Jun	12296782
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
[Antiamebic effect of metronidazole proved in a study conducted in Cienfuegos province].	2002 May-Aug	15849935
Complete remission of Crohn's disease after high-dose cyclophosphamide and autologous stem cell transplantation.	2003 Aug	12858208
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
Molecular mechanisms and biological significance of CTL avidity.	2003 Jul	15046253
[Evaluation on monkeys of reactogenicity and effectiveness of the complex immunoglobulin preparation formulation].	2003 May-Jun	12886634
Diazepam as a treatment for metronidazole toxicosis in dogs: a retrospective study of 21 cases.	2003 May-Jun	12774970
Bone defects of the facial skeleton - replacement with biomaterials.	2003 Nov	15034605
Bronchospasm and laryngeal stridor as an adverse effect of oxytocin treatment.	2003 Oct	12974972
Cardiac diphtheria in a previously immunized individual.	2003 Sep	14527057
[Clinical analysis of unsuccessful Helicobacter pylori eradication].	2004	15603373
[Use of arilin (Dr.Wolff) in the treatment of bacterial vaginosis and trichomoniasis during the period of 01.10.2003-31.12.2003].	2004	15323317
Perforated appendicitis: is laparoscopy safe?	2004 Apr-Jun	15119659
TRICOM: enhanced vaccines as anticancer therapy.	2004 Aug	15270644
Nitazoxanide: a new broad spectrum antiparasitic agent.	2004 Feb	15482170
A case of clarithromycin-induced manic episode (antibiomania).	2004 Mar	14731313
Thoracic spondylitis from a mycotic (Streptococcus pneumoniae) aortic aneurysm: a case report.	2004 Sep 1	15534400
Analyses of recombinant vaccinia and fowlpox vaccine vectors expressing transgenes for two human tumor antigens and three human costimulatory molecules.	2005 Feb 15	15746065
Is operative management effective in treatment of perforated typhoid?	2005 Mar	15792765
Can antibiotics prevent preterm birth--the pro and con debate.	2005 Mar	15715599

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.

Name

Type

Language

METRONIDAZOLE HYDROCHLORIDE

Official Name

English

METRONIDAZOLE HYDROCHLORIDE [MI]

Common Name

English

Metronidazole hydrochloride [WHO-DD]

Common Name

English

2-Methyl-5-nitroimidazole-1-ethanol monohydrochloride

Systematic Name

English

SC-32642

Code

English

METRONIDAZOLE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

FLAGYL I.V.

Brand Name

English

METRONIDAZOLE HCL

Common Name

English

1H-IMIDAZOLE-1-ETHANOL, 2-METHYL-5-NITRO-, HYDROCHLORIDE

Systematic Name

English

METRONIDAZOLE HYDROCHLORIDE [USAN]

Common Name

English

METRONIDAZOLE HYDROCHLORIDE [VANDF]

Common Name

English

METRONIDAZOLE HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C279

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

NCI_THESAURUS

C784

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

Code System Code Type Description

CAS

69198-10-3

Created by admin on Fri Dec 15 15:19:14 GMT 2023 , Edited by admin on Fri Dec 15 15:19:14 GMT 2023

PRIMARY

EVMPD

SUB14570MIG

Created by admin on Fri Dec 15 15:19:14 GMT 2023 , Edited by admin on Fri Dec 15 15:19:14 GMT 2023

PRIMARY

EPA CompTox

DTXSID70219228

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

NCI_THESAURUS

C48005

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

RXCUI

82047

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

RxNorm

CHEBI

50687

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

ChEMBL

CHEMBL137

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

SMS_ID

100000076224

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

PUBCHEM

68592

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

DRUG BANK

DBSALT000362

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

FDA UNII

76JC1633UF

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

MERCK INDEX

m7506

Created by admin on Fri Dec 15 15:19:15 GMT 2023 , Edited by admin on Fri Dec 15 15:19:15 GMT 2023

PRIMARY

Merck Index

ACTIVE MOIETY


					140QMO216E

METRONIDAZOLE

SUBSTANCE RECORD


					76JC1633UF

METRONIDAZOLE HYDROCHLORIDE

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