Éthionamide
Vue d'ensemble
Description
L’éthionamide est un antibiotique synthétique utilisé principalement comme traitement de deuxième intention de la tuberculose, en particulier dans les cas où la maladie est résistante aux médicaments de première intention. Il est également parfois utilisé pour traiter la lèpre. L’éthionamide agit en inhibant la synthèse des acides mycoliques, qui sont des composants essentiels des parois cellulaires des mycobactéries .
Mécanisme D'action
L’éthionamide exerce ses effets en inhibant la synthèse des acides mycoliques, qui sont des composants essentiels de la paroi cellulaire des mycobactéries. Il s’agit d’un promédicament qui nécessite une activation par l’enzyme EthA. Une fois activé, il inhibe l’enzyme InhA, ce qui conduit à la perturbation de la synthèse des acides mycoliques et entraîne finalement la mort cellulaire .
Applications De Recherche Scientifique
L’éthionamide a plusieurs applications en recherche scientifique :
Chimie : Utilisé comme composé modèle pour étudier la synthèse et les réactions des thioamides.
Biologie : Étudié pour ses effets sur la synthèse de la paroi cellulaire des mycobactéries et ses interactions avec d’autres antibiotiques.
Médecine : Largement étudié pour son rôle dans le traitement de la tuberculose multirésistante et ses effets secondaires potentiels.
Industrie : Utilisé dans le développement de nouveaux antibiotiques et dans l’étude des mécanismes de résistance aux médicaments
Méthodes De Préparation
Voies synthétiques et conditions de réaction : L’éthionamide peut être synthétisé par réaction de la 2-éthylpyridine avec du sulfure de carbone et de l’ammoniac, suivie d’une oxydation. Le processus comprend plusieurs étapes :
Formation de la 2-éthylpyridine-4-carbothioamide : Cela est obtenu en faisant réagir la 2-éthylpyridine avec du sulfure de carbone en présence d’ammoniac.
Oxydation : Le composé résultant est ensuite oxydé pour former l’éthionamide.
Méthodes de production industrielle : La production industrielle d’éthionamide implique généralement une synthèse à grande échelle utilisant les mêmes réactions chimiques de base, mais optimisées pour l’efficacité et le rendement. Cela comprend un contrôle précis des conditions de réaction telles que la température, la pression et l’utilisation de catalyseurs pour accélérer les réactions .
Analyse Des Réactions Chimiques
Types de réactions : L’éthionamide subit plusieurs types de réactions chimiques, notamment :
Oxydation : L’éthionamide peut être oxydé pour former le sulfoxyde d’éthionamide, qui est un métabolite actif.
Réduction : L’éthionamide peut être réduit dans certaines conditions, bien que cela soit moins courant.
Substitution : L’éthionamide peut subir des réactions de substitution, en particulier en présence de nucléophiles forts.
Réactifs et conditions courants :
Agents oxydants : Les agents oxydants courants utilisés comprennent le peroxyde d’hydrogène et le permanganate de potassium.
Agents réducteurs : Le borohydrure de sodium et l’hydrure de lithium et d’aluminium sont des agents réducteurs typiques.
Nucléophiles : Des nucléophiles forts tels que le méthylate de sodium peuvent être utilisés pour les réactions de substitution.
Principaux produits :
Sulfoxyde d’éthionamide : Formé par oxydation et est un métabolite actif.
Dérivés substitués : Différents dérivés substitués peuvent être formés en fonction du nucléophile utilisé.
Comparaison Avec Des Composés Similaires
L’éthionamide est similaire à d’autres antibiotiques thioamides tels que la prothionamide et l’isoniazide. Il possède des propriétés uniques qui le rendent particulièrement utile dans le traitement de la tuberculose multirésistante :
Prothionamide : Structure et fonction similaires, mais propriétés pharmacocinétiques différentes.
Isoniazide : Inhibe également la synthèse des acides mycoliques, mais par une voie d’activation différente.
Pyrazinamide : Autre médicament antituberculeux qui agit par un mécanisme différent, mais est souvent utilisé en association avec l’éthionamide .
La capacité de l’éthionamide à traverser la barrière hémato-encéphalique et son efficacité contre les souches résistantes de mycobactéries en font un médicament précieux dans la lutte contre la tuberculose .
Propriétés
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 | |
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| 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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| Record name | Ethionamide | |
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| Record name | Ethionamide | |
| Source | European Chemicals Agency (ECHA) | |
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| Record name | ETHIONAMIDE | |
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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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| 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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