エチオナミド
概要
説明
エチオナミドは、主に結核の第二選択薬として使用される合成抗生物質であり、特に第一選択薬に耐性のある結核の場合に使用されます。また、まれにらい菌の治療にも使用されます。 エチオナミドは、マイコバクテリアの細胞壁の重要な構成要素であるマイコ酸の合成を阻害することで作用します .
2. 製法
合成経路と反応条件： エチオナミドは、2-エチルピリジンを二硫化炭素とアンモニアと反応させ、その後酸化することで合成することができます。このプロセスは、いくつかの段階を含みます。
2-エチルピリジン-4-カルボチオアミドの形成： これは、2-エチルピリジンをアンモニアの存在下で二硫化炭素と反応させることで達成されます。
工業生産方法： エチオナミドの工業生産は、通常、同じ基本的な化学反応を使用しますが、効率と収率を高めるために最適化された大規模な合成を行います。 これには、温度、圧力などの反応条件を精密に制御し、触媒を使用して反応を加速させることが含まれます .
3. 化学反応解析
反応の種類： エチオナミドは、以下を含むいくつかの種類の化学反応を起こします。
酸化： エチオナミドは、酸化されてエチオナミドスルホキシドを生成することができ、これは活性代謝産物です。
還元： エチオナミドは、特定の条件下では還元され得ますが、これはそれほど一般的ではありません。
一般的な試薬と条件：
酸化剤： 使用される一般的な酸化剤には、過酸化水素と過マンガン酸カリウムがあります。
還元剤： 水素化ホウ素ナトリウムと水素化リチウムアルミニウムは、一般的な還元剤です。
主な生成物：
エチオナミドスルホキシド： 酸化によって生成され、活性代謝産物です。
置換誘導体： 使用される求核剤に応じて、さまざまな置換誘導体が形成され得ます.
4. 科学研究への応用
エチオナミドは、科学研究においていくつかの応用があります。
化学： チオアミドの合成と反応を研究するためのモデル化合物として使用されます。
生物学： マイコバクテリアの細胞壁合成への影響と、他の抗生物質との相互作用について研究されています。
医学： 多剤耐性結核の治療における役割とその潜在的な副作用について、広く研究されています。
作用機序
エチオナミドは、マイコバクテリアの細胞壁の重要な構成要素であるマイコ酸の合成を阻害することで作用します。これは、EthA酵素による活性化を必要とするプロドラッグです。 活性化されると、InhA酵素を阻害し、マイコ酸合成を阻害し、最終的に細胞死を引き起こします .
6. 類似の化合物との比較
エチオナミドは、プロチオナミドやイソニアジドなどの他のチオアミド系抗生物質と類似しています。それは、多剤耐性結核の治療に特に有用にする独自の特性を持っています。
プロチオナミド： 構造と機能が似ていますが、薬物動態が異なります。
イソニアジド： マイコ酸合成を阻害しますが、異なる活性化経路を介します。
ピラジナミド： 異なるメカニズムで作用する別の抗結核薬ですが、エチオナミドと組み合わせて使用されることがよくあります .
エチオナミドは、血脳関門を通過する能力と、耐性菌株のマイコバクテリアに対する有効性により、結核との闘いにおいて貴重な薬となっています .
科学的研究の応用
Ethionamide has several applications in scientific research:
Chemistry: Used as a model compound to study the synthesis and reactions of thioamides.
Biology: Studied for its effects on mycobacterial cell wall synthesis and its interactions with other antibiotics.
Medicine: Extensively researched for its role in treating multidrug-resistant tuberculosis and its potential side effects.
Industry: Used in the development of new antibiotics and in the study of drug resistance mechanisms
準備方法
Synthetic Routes and Reaction Conditions: Ethionamide can be synthesized through the reaction of 2-ethylpyridine with carbon disulfide and ammonia, followed by oxidation. The process involves several steps:
Formation of 2-ethylpyridine-4-carbothioamide: This is achieved by reacting 2-ethylpyridine with carbon disulfide in the presence of ammonia.
Oxidation: The resulting compound is then oxidized to form ethionamide.
Industrial Production Methods: Industrial production of ethionamide typically involves large-scale synthesis using the same basic chemical reactions but optimized for efficiency and yield. This includes precise control of reaction conditions such as temperature, pressure, and the use of catalysts to speed up the reactions .
化学反応の分析
Types of Reactions: Ethionamide undergoes several types of chemical reactions, including:
Oxidation: Ethionamide can be oxidized to form ethionamide sulfoxide, which is an active metabolite.
Reduction: Ethionamide can be reduced under certain conditions, although this is less common.
Substitution: Ethionamide can undergo substitution reactions, particularly in the presence of strong nucleophiles.
Common Reagents and Conditions:
Oxidizing Agents: Common oxidizing agents used include hydrogen peroxide and potassium permanganate.
Reducing Agents: Sodium borohydride and lithium aluminum hydride are typical reducing agents.
Nucleophiles: Strong nucleophiles such as sodium methoxide can be used for substitution reactions.
Major Products:
Ethionamide Sulfoxide: Formed through oxidation and is an active metabolite.
Substituted Derivatives: Various substituted derivatives can be formed depending on the nucleophile used.
類似化合物との比較
Ethionamide is similar to other thioamide antibiotics such as prothionamide and isoniazid. it has unique properties that make it particularly useful in treating multidrug-resistant tuberculosis:
Prothionamide: Similar in structure and function but has different pharmacokinetic properties.
Isoniazid: Also inhibits mycolic acid synthesis but through a different activation pathway.
Pyrazinamide: Another antitubercular drug that works through a different mechanism but is often used in combination with ethionamide .
Ethionamide’s ability to cross the blood-brain barrier and its effectiveness against resistant strains of mycobacteria make it a valuable drug in the fight against tuberculosis .
特性
IUPAC Name |
2-ethylpyridine-4-carbothioamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
AEOCXXJPGCBFJA-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCC1=NC=CC(=C1)C(=S)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C8H10N2S |
Source
|
| Record name | ETHIONAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20353 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0020577 |
Source
|
| Record name | Ethionamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0020577 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
166.25 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Ethionamide appears as yellow crystals or canary yellow powder with a faint to moderate sulfide odor. (NTP, 1992), Solid |
Source
|
| Record name | ETHIONAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20353 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Ethionamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014747 | |
| 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 |
less than 1 mg/mL at 70 °F (NTP, 1992), Practically insoluble, Very sparingly soluble in ether. Sparingly soluble in methanol, ethanol, propylene glycol. Soluble in hot acetone, dichloroethane. Freely soluble in pyridine., 8.39e-01 g/L |
Source
|
| Record name | ETHIONAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20353 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Ethionamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00609 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | ETHIONAMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7473 | |
| 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 | Ethionamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014747 | |
| 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 |
Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Ethionamide, like prothionamide and pyrazinamide, is a nicotinic acid derivative related to isoniazid. It is thought that ethionamide undergoes intracellular modification and acts in a similar fashion to isoniazid. Isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA., Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. The exact mechanism of action of ethionamide has not been fully elucidated, but the drug appears to inhibit peptide synthesis in susceptible organisms. |
Source
|
| Record name | Ethionamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00609 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | ETHIONAMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7473 | |
| 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 |
Yellow crystals from ethanol | |
CAS No. |
536-33-4 |
Source
|
| Record name | ETHIONAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20353 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Ethionamide | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=536-33-4 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Ethionamide [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000536334 | |
| 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. | |
| Record name | Ethionamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00609 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | ethionamide | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=757028 | |
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| Record name | ethionamide | |
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| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=255115 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
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| Record name | Ethionamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0020577 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Ethionamide | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.007.846 | |
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| Record name | ETHIONAMIDE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/OAY8ORS3CQ | |
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| Record name | ETHIONAMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7473 | |
| 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 | Ethionamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014747 | |
| 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 |
327 to 331 °F (Decomposes) (NTP, 1992), 164-166 °C (decomposes), 163 °C |
Source
|
| Record name | ETHIONAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20353 | |
| 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. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Ethionamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00609 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | ETHIONAMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7473 | |
| 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 | Ethionamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014747 | |
| 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
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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
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