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
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
DescriptionCurator's Comment: description was created based on several sources, including
http://www.emedexpert.com/facts/metronidazole-facts.shtml
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2364041 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | FLAGYL Approved UseINDICATIONS & 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 Date1963 |
|||
| Curative | FLAGYL Approved UseINDICATIONS & 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 Date1963 |
|||
| Curative | FLAGYL Approved UseINDICATIONS & 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 Date1963 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12 μg/mL |
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 |
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 |
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 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8 h |
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 |
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 |
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 |
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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
80% |
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 |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (9.6%) Sources: |
8.5 g single, oral Overdose |
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: |
|
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: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
DLT: Nausea and vomiting, Generalised onset motor seizure... Dose limiting toxicities: Nausea and vomiting (13.5%) Sources: Generalised onset motor seizure (12.8%) Neurotoxicity NOS (10.9%) |
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: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
DLT: Gastrointestinal toxicity, Central nervous system toxicity... Dose limiting toxicities: Gastrointestinal toxicity (14.5%) Sources: Central nervous system toxicity (13.7%) |
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: |
unhealthy, preterm newborn n = 1 Health Status: unhealthy Condition: bloody stools and apnoea Age Group: preterm newborn Sex: F Population Size: 1 Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hepatotoxicity | 9.6% Disc. AE |
12.5 g single, oral Overdose |
unhealthy, 58 years n = 1 Health Status: unhealthy Condition: chronic depressive illness Age Group: 58 years Sex: F Population Size: 1 Sources: |
| 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: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
| 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: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
| 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: |
unhealthy, adult n = 32 Health Status: unhealthy Condition: advanced carcinoma of the colon or rectum Age Group: adult Sex: unknown Population Size: 32 Sources: |
| 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: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
| 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: |
unhealthy, adult n = 28 Health Status: unhealthy Condition: malignant brain tumors Age Group: adult Sex: unknown Population Size: 28 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Do ethanol and metronidazole interact to produce a disulfiram-like reaction? | 2000 Feb |
|
| Mesalamine-induced chest pain: a case report. | 2000 May |
|
| A simple, efficient and inexpensive program for preventing prematurity. | 2001 |
|
| Technology evaluation: CEA-TRICOM, Therion Biologics Corp. | 2001 Aug |
|
| Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis. | 2001 Jun 15 |
|
| [The efficacy of the Helicobacter pylori eradication in people of an advanced age]. | 2002 |
|
| Vaccine-based therapy directed against carcinoembryonic antigen demonstrates antitumor activity on spontaneous intestinal tumors in the absence of autoimmunity. | 2002 Dec 1 |
|
| [Fever and weight loss as leading symptoms of infection with giardia lamblia]. | 2002 Feb |
|
| Antimicrobial-induced mania (antibiomania): a review of spontaneous reports. | 2002 Feb |
|
| Effects of non-surgical treatment modalities on peri-implantitis. | 2002 May |
|
| [Antiamebic effect of metronidazole proved in a study conducted in Cienfuegos province]. | 2002 May-Aug |
|
| Complete remission of Crohn's disease after high-dose cyclophosphamide and autologous stem cell transplantation. | 2003 Aug |
|
| Renal papillary necrosis induced by naproxen. | 2003 Aug |
|
| [Vulvar amebiasis. Report of a case and review of the literature]. | 2003 Feb |
|
| Role of bacteria and inducible nitric oxide synthase activity in the systemic inflammatory microvascular response provoked by indomethacin in the rat. | 2003 Feb 7 |
|
| Molecular mechanisms and biological significance of CTL avidity. | 2003 Jul |
|
| Bone defects of the facial skeleton - replacement with biomaterials. | 2003 Nov |
|
| Crohn's disease--when to operate? | 2004 |
|
| [Efficacy of two Helicobacter pylori eradication treatments in children with recurrent abdominal pain]. | 2004 Apr-Jun |
|
| Nitazoxanide: a new broad spectrum antiparasitic agent. | 2004 Feb |
|
| [Tetanus in cats: 3 case descriptions]. | 2004 Jun |
|
| Reversible cerebellar lesions induced by metronidazole therapy for helicobacter pylori. | 2004 Oct |
|
| Thoracic spondylitis from a mycotic (Streptococcus pneumoniae) aortic aneurysm: a case report. | 2004 Sep 1 |
|
| Analyses of recombinant vaccinia and fowlpox vaccine vectors expressing transgenes for two human tumor antigens and three human costimulatory molecules. | 2005 Feb 15 |
|
| Is operative management effective in treatment of perforated typhoid? | 2005 Mar |
|
| [Two cases of metronidazole-induced encephalopathy]. | 2005 Mar |
|
| Abnormal enhancing lesion of dentate nuclei causing neurologic symptoms induced by metronidazole toxicity. | 2005 Mar |
Sample Use Guides
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
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.
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165412101
Created by
admin on Sat Dec 16 18:41:25 GMT 2023 , Edited by admin on Sat Dec 16 18:41:25 GMT 2023
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8LKQ4FU9YN
Created by
admin on Sat Dec 16 18:41:25 GMT 2023 , Edited by admin on Sat Dec 16 18:41:25 GMT 2023
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
