metronidazole citrate

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H15N3O9
Molecular Weight	345.2622
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BSDGJHSABQWHHI-UHFFFAOYSA-N

InChI=1S/C12H15N3O9/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)

HIDE SMILES / InChI

Molecular Formula	C12H15N3O9
Molecular Weight	345.2622
Charge	0
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 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
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.	1992	1288759
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
[Antiamebic effect of metronidazole proved in a study conducted in Cienfuegos province].	2002 May-Aug	15849935
The importance of Bi-Digital O-Ring Test in the treatment of multiple hepatic abscesses: a case history.	2003	14998058
[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
[Comparative clinical and epidemiological evaluation of beta-lactam antibiotics in the treatment of intraabdominal infections].	2003	12914120
An unexpected and severe neurological disorder with permanent disability acquired during short-course treatment with metronidazole.	2003	12839161
Superior mesenteric vein thrombosis following laparoscopic Nissen fundoplication.	2003 Apr-Jun	12856849
An open label crossover trial of effects of metronidazol on hyperlipidaemia.	2003 Aug	12957743
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
Analysis of antimicrobial susceptibility and virulence factors in Helicobacter pylori clinical isolates.	2003 Aug 11	12911839
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
Molecular mechanisms and biological significance of CTL avidity.	2003 Jul	15046253
A triad of costimulatory molecules synergize to amplify T-cell activation in both vector-based and vector-infected dendritic cell vaccines.	2003 May	12751840
[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
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
[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
[Efficacy of two Helicobacter pylori eradication treatments in children with recurrent abdominal pain].	2004 Apr-Jun	15757155
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
Lemierre's syndrome: the forgotten disease. An unusual presentation of sepsis.	2004 Feb	14961428
Reduced stem cell mobilization in mice receiving antibiotic modulation of the intestinal flora: involvement of endotoxins as cofactors in mobilization.	2004 Jan 1	12969972
[Tetanus in cats: 3 case descriptions].	2004 Jun	15248349
A case of clarithromycin-induced manic episode (antibiomania).	2004 Mar	14731313
Reproductive and cytogenetic toxicity of metronidazole in male mice.	2004 May	15125692
Experience with routine intraabdominal cultures during laparoscopic gastric bypass with implications for antibiotic prophylaxis.	2004 May	14752648
Reversible cerebellar lesions induced by metronidazole therapy for helicobacter pylori.	2004 Oct	15358960
Thoracic spondylitis from a mycotic (Streptococcus pneumoniae) aortic aneurysm: a case report.	2004 Sep 1	15534400
Metronidazole-induced encephalopathy.	2004 Sep 15	15450780
Phase I study of sequential vaccinations with fowlpox-CEA(6D)-TRICOM alone and sequentially with vaccinia-CEA(6D)-TRICOM, with and without granulocyte-macrophage colony-stimulating factor, in patients with carcinoembryonic antigen-expressing carcinomas.	2005 Feb 1	15613691
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
[Two cases of metronidazole-induced encephalopathy].	2005 Mar	15778547
Abnormal enhancing lesion of dentate nuclei causing neurologic symptoms induced by metronidazole toxicity.	2005 Mar	15765436
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:43:03 GMT 2023` Edited by `admin` on `Sat Dec 16 18:43:03 GMT 2023`
Record UNII	8Y356BW999
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

metronidazole citrate

Common Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

8Y356BW999

Created by admin on Sat Dec 16 18:43:04 GMT 2023 , Edited by admin on Sat Dec 16 18:43:04 GMT 2023

PRIMARY

PUBCHEM

165412102

Created by admin on Sat Dec 16 18:43:04 GMT 2023 , Edited by admin on Sat Dec 16 18:43:04 GMT 2023

PRIMARY

Related Record Type Details


					8LKQ4FU9YN

Metronidazole citrate disodium

SALT/SOLVATE -> PARENT

Amount:

Related Record Type Details


					140QMO216E

METRONIDAZOLE

METABOLITE ACTIVE -> PRODRUG

Amount:

Related Record Type Details


					140QMO216E

METRONIDAZOLE

ACTIVE MOIETY

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