メトロニダゾール

カタログ番号: B1676534

CAS番号: 443-48-1

分子量: 171.15 g/mol

InChIキー: VAOCPAMSLUNLGC-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

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概要

1. 説明

6. 類似化合物との比較

2. 作用機序

7. 特性

3. 科学的研究の応用

8. Retrosynthesis analysis

4. 準備方法

9. Q & A

5. 化学反応の分析

10. 免責事項

説明

メトロニダゾールは、フラジール などのブランド名で販売されている抗生物質および抗原虫薬です。
骨盤炎症性疾患、心内膜炎、細菌性膣症、ドラクンキュリアーシス、ジアルジア症、トリコモナス症、アメーバ症などのさまざまな感染症の治療に使用されます .
メトロニダゾールは、嫌気性細菌と特定の寄生虫に効果があります。

作用機序

メトロニダゾールは嫌気性細菌に入り、活性化され、短命のニトロソフリーラジカルに還元されます。
このラジカルはDNAと相互作用し、らせん構造の損失、鎖の切断、細菌の死を引き起こします。

類似化合物の比較

メトロニダゾールは、細菌と原虫に対する二重作用が特徴です。
類似の化合物には、チニダゾールとセクニダゾールがあります .

科学的研究の応用

Medicine: Metronidazole is widely used in medicine to treat anaerobic bacterial infections, protozoal infections, and certain sexually transmitted infections.

Dentistry: It’s used for oral infections and periodontal diseases.

Veterinary Medicine: Metronidazole is also employed in veterinary practice.

準備方法

合成経路: メトロニダゾールは、ヒドラジンまたは水素化ホウ素ナトリウムによる2-メチル-5-ニトロイミダゾールの還元など、いくつかの方法で合成できます。

工業生産: 商業生産には化学合成が関与し、ニトロ基は嫌気的条件下でアミノ基に還元されます。

化学反応の分析

反応: メトロニダゾールは、還元、置換、環化など、さまざまな反応を起こします。

一般的な試薬: ヒドラジンや水素化ホウ素ナトリウムなどの還元剤が還元工程に使用されます。

主な生成物: ニトロ基の還元により、メトロニダゾールの活性型であるアミノ誘導体が生成されます。

科学研究への応用

医学: メトロニダゾールは、嫌気性細菌感染症、原虫感染症、特定の性感染症の治療に広く使用されています。

歯科: 口腔感染症や歯周病に使用されています。

獣医学: メトロニダゾールは、獣医学でも使用されています。

類似化合物との比較

Metronidazole is unique due to its dual action against bacteria and protozoa.
Similar compounds include tinidazole and secnidazole .

特性

IUPAC Name	2-(2-methyl-5-nitroimidazol-1-yl)ethanol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	VAOCPAMSLUNLGC-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC1=NC=C(N1CCO)[N+](=O)[O-]	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C6H9N3O3	Source
Record name	METRONIDAZOLE
Source	CAMEO Chemicals
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Record name	metronidazole
Source	Wikipedia
URL	https://en.wikipedia.org/wiki/Metronidazole
Description	Chemical information link to Wikipedia.

Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	69198-10-3 (mono-hydrochloride)	Source
Record name	Metronidazole [USAN:USP:INN:BAN:JAN]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000443481
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

DSSTOX Substance ID	DTXSID2020892	Source
Record name	Metronidazole
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID2020892
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	171.15 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Metronidazole is a white to pale-yellow crystalline powder with a slight odor. Bitter and saline taste. pH (saturated aqueous solution) about 6.5. (NTP, 1992), Solid	Source
Record name	METRONIDAZOLE
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Record name	Metronidazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015052
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Solubility	>25.7 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 68 °F (NTP, 1992), g/100 ml at 20 °C: 1.0 in water, 0.5 in ethanol, less than 0.05 in ether, chloroform; sol in dilute acids; sparingly sol in dimethylformamide, In water, 11,000 mg/L at 25 °C, 5.92e+00 g/L	Source
Record name	SID855672
Source	Burnham Center for Chemical Genomics
URL	https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table
Description	Aqueous solubility in buffer at pH 7.4

Record name	METRONIDAZOLE
Source	CAMEO Chemicals
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Record name	METRONIDAZOLE
Source	Hazardous Substances Data Bank (HSDB)
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Record name	Metronidazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015052
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action	The exact mechanism of action of metronidazole has not been fully established, however, it is possible that an intermediate in the reduction of metronidazole which is only made by anaerobic bacteria and protozoa, binds deoxyribonucleic acid and electron-transport proteins of organisms, blocking nucleic acid synthesis. After administration, metronidazole enters cells by passive diffusion. Following this, ferredoxin or flavodoxin reduce its nitro group to nitro radicals. The redox potential of the electron transport portions of anaerobic or microaerophilic microorganisms renders metronidazole selective to these organisms, which cause nitro group reduction, leading to the production of toxic metabolites. These include N-(2-hydroxyethyl) oxamic acid and acetamide, which may damage DNA of replicating organisms., Microbicidal; active against most obligate anaerobic bacteria and protozoa by undergoing intracellular chemical reduction via mechanisms unique to anaerobic metabolism. Reduced metronidazole, which is cytotoxic but short-lived, interacts with DNA to cause loss of helical structure, strand breakage, and resultant inhibition of nucleic acid synthesis and cell death., Metronidazole is bactericidal, amebicidal, and trichomonacidal in action. The exact mechanism of action of the drug has not been fully elucidated. Metronidazole is un-ionized at physiologic pH and is readily taken up by anaerobic organisms or cells. In susceptible organisms or cells, metronidazole is reduced by low-redox-potential electron transport proteins (e.g., nitroreductases such as ferredoxin) to unidentified polar product(s) which lack the nitro group. The reduction product(s) appears to be responsible for the cytotoxic and antimicrobial effects of the drug which include disruption of DNA and inhibition of nucleic acid synthesis. Metronidazole is equally effective against dividing and nondividing cells., In in vivo studies in rats given metronidazole in dosages of 2-4 mg/100 g of body weight, the drug reportedly inhibited the development of formalin-induced edema in the rat paw. In vitro in neutrophils, metronidazole has a dose-dependent inhibitory effect on generation of hydrogen peroxide and hydroxyl radicals, oxidants that may cause tissue injury at the site of inflammation. This antioxidant effect appears to be caused by a direct effect on neutrophil function and may contribute to the drug's anti-inflammatory effect in vivo., Results of in vitro studies using leukocytes obtained from patients with Crohn's disease indicate that exposing the cells to metronidazole concentrations of 10 or 50 mcg/mL improved both spontaneous and induced leukocyte migration in cells that previously exhibited reduced migration; the drug had no effect on leukocytes obtained from healthy adults or patients with Crohn's disease when the cells exhibited normal migration prior to exposure to the drug. This effect on leukocyte migration also was observed in vivo in adults with Crohn's disease who received a single 400-mg dose of metronidazole. It has been suggested that metronidazole may increase leukocyte migration by a direct effect on the leukocytes, possibly by causing the release of surface-bound immune complexes from the cell surface.	Source
Record name	Metronidazole
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URL	https://www.drugbank.ca/drugs/DB00916
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Record name	METRONIDAZOLE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3129
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Color/Form	Cream-colored crystals, WHITE TO PALE YELLOW CRYSTALS OR CRYSTALLINE POWDER
CAS No.	443-48-1, 56010-45-8	Source
Record name	METRONIDAZOLE
Source	CAMEO Chemicals
URL	https://cameochemicals.noaa.gov/chemical/20708
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Record name	Metronidazole
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Record name	1H-Imidazole-1-ethanol, 2-methyl-5-nitro-, radical ion(1-)
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Record name	Metronidazole [USAN:USP:INN:BAN:JAN]
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Record name	Metronidazole
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Record name	metronidazole
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Record name	Metronidazole
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Record name	Metronidazole
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Record name	METRONIDAZOLE
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Record name	METRONIDAZOLE
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Record name	Metronidazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015052
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	316 to 320 °F (NTP, 1992), 158-160 °C, 160 °C	Source
Record name	METRONIDAZOLE
Source	CAMEO Chemicals
URL	https://cameochemicals.noaa.gov/chemical/20708
Description	CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management.
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Record name	Metronidazole
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URL	https://www.drugbank.ca/drugs/DB00916
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Record name	METRONIDAZOLE
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URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3129
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Metronidazole
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015052
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Metronidazole

Reactant of Route 2

Metronidazole

Reactant of Route 3

Metronidazole

Reactant of Route 4

Metronidazole

Reactant of Route 5

Metronidazole

Reactant of Route 6

Metronidazole

Customer

Q & A

Q1: How does Metronidazole exert its antimicrobial effect?

A1: Metronidazole is a prodrug that requires reductive activation within anaerobic or microaerophilic microorganisms. [] This process involves the reduction of its nitro group, likely by enzymes like thioredoxin reductase and pyruvate:ferredoxin oxidoreductase. [, ] This reduction generates cytotoxic metabolites that disrupt DNA synthesis and cause strand breakage, ultimately leading to cell death. [] It's important to note that this mechanism is selective for anaerobic bacteria due to their unique metabolic pathways and redox potential. []

Q2: Metronidazole is known for its activity against Trichomonas vaginalis. Can you elaborate on this?

A2: Research shows that Metronidazole disrupts the cellular redox system in Trichomonas vaginalis. [] Specifically, Metronidazole's metabolites form adducts with proteins involved in thioredoxin-mediated redox regulation, hindering essential processes and causing cell death. []

Q3: What is known about the stability of Metronidazole in different formulations?

A5: Research indicates that Metronidazole demonstrates good stability in various formulations. For instance, Metronidazole benzoate suspension in SyrSpend SF One-Step Suspension system remained stable for at least one year at ambient temperature and potentially two years under refrigerated conditions. [] Additionally, extemporaneously prepared Metronidazole cream exhibited stability for six months. []

Q4: Can you provide specific examples of Metronidazole's stability in intravenous admixtures?

A6: Studies have investigated the stability of Metronidazole in combination with other drugs. One study demonstrated that a mixture of Cefotaxime sodium (10 mg/mL) and Metronidazole (5 mg/mL) remained stable for 72 hours at 8°C in an intravenous admixture. [] Similarly, another study found that Cefepime hydrochloride and Metronidazole mixtures in various solutions and concentrations exhibited stability for varying durations at 4°C and 22-24°C when stored in polyvinyl chloride bags. [] These findings highlight the importance of considering storage conditions and specific drug combinations when assessing the stability of Metronidazole admixtures.

Q5: How does the polymerization process affect Metronidazole's release from Polymethylmethacrylate (PMMA) beads?

A7: Research has explored incorporating Metronidazole into PMMA beads for local drug delivery. [] Studies show that Metronidazole's elution from PMMA is dose-dependent. [] Interestingly, copolymerization of Metronidazole with Gentamicin sulfate within PMMA resulted in increased elution rates for both drugs. [] These findings suggest the potential for tailoring drug release profiles by manipulating drug concentrations and combinations during the polymerization process.

Q6: What is the prevalence of Metronidazole resistance, and are there alternative treatments?

A8: Metronidazole resistance is a growing concern. Studies show a high frequency of resistance among Campylobacter jejuni strains isolated from birds (82-100%), while resistance is less common in isolates from ruminants. [] For Helicobacter pylori infections, Furazolidone has been investigated as an alternative in patients with Metronidazole-resistant strains, showing promising eradication rates and good tolerability. []

Q7: Are there any natural alternatives to Metronidazole for conditions like bacterial vaginosis?

A9: A randomized clinical trial compared Mycocin vaginal cream, composed of garlic and thyme, to Metronidazole vaginal gel for treating bacterial vaginosis. [] The study found comparable clinical improvement in both groups, suggesting Mycocin as a potential alternative treatment option. [] This highlights the ongoing search for alternative therapies to combat antimicrobial resistance and potentially reduce side effects.

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