Albendazole
Vue d'ensemble
Description
L’albendazole est un agent anthelminthique et antiprotozoaire à large spectre appartenant à la classe des benzimidazoles. Il est principalement utilisé pour traiter diverses infestations parasitaires par des vers, y compris celles causées par des nématodes, des cestodes et des trématodes . L'this compound a été développé en 1975 et figure sur la Liste des médicaments essentiels de l'Organisation mondiale de la santé .
Mécanisme D'action
L’albendazole exerce ses effets en se liant au site sensible à la colchicine de la tubuline, inhibant sa polymérisation en microtubules. Cette perturbation de la formation des microtubules entraîne des altérations dégénératives dans les cellules intestinales des parasites, entraînant finalement leur mort . La cible moléculaire principale est la tubuline, et la voie impliquée est l’inhibition de la polymérisation des microtubules .
Analyse Biochimique
Biochemical Properties
Albendazole interacts with tubulin, a protein that forms the cytoskeleton of cells . By binding to the colchicine-sensitive site of tubulin, this compound inhibits its polymerization or assembly into microtubules . This interaction disrupts the cytoskeleton of the cells, leading to their immobilization and death .
Cellular Effects
This compound has a significant impact on various types of cells and cellular processes. It influences cell function by disrupting the cytoskeleton, which is crucial for cell shape, division, and intracellular transport . This disruption can affect cell signaling pathways, gene expression, and cellular metabolism .
Molecular Mechanism
The principal mode of action for this compound is its inhibitory effect on tubulin polymerization, which results in the loss of cytoplasmic microtubules . This mechanism leads to degenerative alterations in the tegument and intestinal cells of the worm, diminishing its energy production and leading to the immobilization and death of the parasite .
Metabolic Pathways
This compound is involved in metabolic pathways that lead to its transformation into metabolites: this compound sulphoxide (ABZSO) and this compound sulphone (ABZSO2) . These metabolites are formed in the body after administration of this compound .
Méthodes De Préparation
Voies de synthèse et conditions de réaction
L’albendazole peut être synthétisé par plusieurs voies. Une méthode courante implique l’utilisation de la 2-nitro-5-chloroaniline comme matière première. Ce composé subit une série de réactions, y compris la substitution, la condensation, la réduction et la cyclisation, pour donner l’this compound . Le procédé évite l’utilisation d’une réduction par hydrogénation à haut risque et utilise plutôt un procédé de réduction par un sulfure alcalin, qui est plus sûr et plus rentable .
Méthodes de production industrielle
En milieu industriel, l’this compound est souvent produit en utilisant un système de solvants mixtes (eau et éthanol) et un système d’acides mixtes (acide formique et acide acétique) pour le raffinage. Cette méthode donne un this compound de pureté et de solubilité supérieures . De plus, l’this compound peut être formulé en microcapsules ciblées vers le côlon pour améliorer son absorption et son efficacité .
Analyse Des Réactions Chimiques
Types de réactions
L’albendazole subit diverses réactions chimiques, notamment l’oxydation, la réduction et la substitution.
Réactifs et conditions courants
Réduction : Le processus de réduction dans la synthèse de l’this compound implique l’utilisation d’un sulfure alcalin.
Substitution : La réaction de substitution initiale dans la synthèse implique la 2-nitro-5-chloroaniline et le n-propane halogéné.
Principaux produits
Applications de la recherche scientifique
L’this compound a un large éventail d’applications dans la recherche scientifique :
Chimie : Il est utilisé comme composé modèle dans des études portant sur les dérivés benzimidazoles.
Applications De Recherche Scientifique
Albendazole has a wide range of applications in scientific research:
Chemistry: It is used as a model compound in studies involving benzimidazole derivatives.
Comparaison Avec Des Composés Similaires
L’albendazole est souvent comparé à d’autres anthelminthiques benzimidazoles tels que le mébendazole et le fénbendazole. Bien que les trois composés partagent un mécanisme d’action similaire, l’this compound est unique en raison de son spectre d’activité plus large et de son efficacité supérieure contre certaines infections parasitaires .
Composés similaires
Propriétés
IUPAC Name |
methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HXHWSAZORRCQMX-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H15N3O2S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0022563 |
Source
|
| Record name | Albendazole | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0022563 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
265.33 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Albendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014659 | |
| 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 |
1.4 [ug/mL] (The mean of the results at pH 7.4), Practically insoluble, 2.28e-02 g/L |
Source
|
| Record name | SID855809 | |
| 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 | Albendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00518 | |
| 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 | Albendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014659 | |
| 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 |
Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by diminishing its energy production, ultimately leading to immobilization and death of the parasite. It works by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. As cytoplasmic microtubules are critical in promoting glucose uptake in larval and adult stages of the susceptible parasites, the glycogen stores of the parasites are depleted. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth., Benzimidazoles produce many biochemical changes in susceptible nematodes, eg, inhibition of mitochondrial fumarate reductase, reduced glucose transport, and uncoupling of oxidative phosphorylation ... /but/ the primary action ... /should be/ to inhibit microtubule polymerization by binding to beta-tubulin. The selective toxicity of these agents derives from the fact that specific, high-affinity binding to parasite beta-tubulin occurs at much lower concn than does binding to the mammalian protein ... Benzimidazole-resistant Haemonchus contortus display reduced high-affinity drug binding to beta-tubulin and alterations in beta-tubulin isotype gene expression that correlate with drug resistance ... Two identified mechanisms of drug resistance in nematodes involve both a progressive loss of "susceptible" beta-tubulin gene isotypes together with emergence of a "resistant" isotype with a conserved point mutation that encodes a tyrosine instead of phenylalanine at position 200 of beta-tubulin. While this mutation may not be required for benzimidazole resistance in all parasites, eg, Giardia lamblia, benzimidazole resistance in parasitic nematodes is unlikely to be overcome by novel benzimidazole analogs, because tyrosine also is present at position 200 of human beta-tubulin. /Benzimidazoles/, Although the exact mechanism of action of albendazole has not been fully elucidated, the principal anthelmintic effect of benzimidazoles, including albendazole, appears to be the specific, high-affinity binding of the drug to free beta-tubulin in parasite cells, resulting in selective inhibition of parasite microtubule polymerization, and inhibition of microtubule-dependent uptake of glucose. Benzimidazole drugs bind to the beta-tubulin of parasites at much lower concentrations than to mammalian beta-tubulin protein; the drugs do not inhibit glucose uptake in mammals, and do not appear to have any effect on blood glucose concentrations in humans, The mode of action of albendazole is by binding strongly with the tubulin in the cells of nematodes. The intestinal cells of the nematode are particularly affected, resulting in a loss of absorptive function which causes the nematodes to starve to death. |
Source
|
| Record name | Albendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00518 | |
| 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 | ALBENDAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7444 | |
| 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 |
Colorless crystals | |
CAS No. |
54965-21-8 |
Source
|
| Record name | Albendazole | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=54965-21-8 | |
| 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. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Albendazole [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0054965218 | |
| 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 | Albendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00518 | |
| 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 | albendazole | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=758644 | |
| 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 | albendazole | |
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| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=220008 | |
| 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 | Albendazole | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0022563 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Albendazole | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.053.995 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
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| Record name | ALBENDAZOLE | |
| Source | FDA Global Substance Registration System (GSRS) | |
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| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
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| Record name | ALBENDAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7444 | |
| 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 | Albendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014659 | |
| 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 |
208-210, 208-210 °C, Mol wt: 281.34. Active metabolite of albendazole. MP: 226-228 °C (decomposes) /Sulfoxide/, 209 °C |
Source
|
| Record name | Albendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00518 | |
| 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 | ALBENDAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7444 | |
| 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 | Albendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014659 | |
| 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. | |
Synthesis routes and methods I
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Synthesis routes and methods II
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Retrosynthesis Analysis
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| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
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