アルベンダゾール
カタログ番号:
B1665689
CAS番号:
54965-21-8
分子量:
265.33 g/mol
InChIキー:
HXHWSAZORRCQMX-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。
概要
説明
アルベンダゾールは、ベンゾイミダゾール系化合物に属する広域スペクトル駆虫剤および抗原虫剤です。 主に、回虫、条虫、吸虫など、さまざまな寄生虫による感染症の治療に使用されます 。 アルベンダゾールは1975年に開発され、世界保健機関の必須医薬品リストに掲載されています .
作用機序
アルベンダゾールは、チューブリンのコルヒチン感受性部位に結合することにより、その微小管への重合を阻害することで効果を発揮します。 この微小管形成の阻害は、寄生虫の腸細胞の変性変化を引き起こし、最終的には寄生虫の死に至ります 。 主な分子標的はチューブリンであり、関与する経路は微小管重合の阻害です .
科学的研究の応用
Albendazole has a wide range of applications in scientific research:
Chemistry: It is used as a model compound in studies involving benzimidazole derivatives.
生化学分析
Biochemical Properties
Albendazole interacts with tubulin, a protein that forms the cytoskeleton of cells . By binding to the colchicine-sensitive site of tubulin, Albendazole inhibits its polymerization or assembly into microtubules . This interaction disrupts the cytoskeleton of the cells, leading to their immobilization and death .
Cellular Effects
Albendazole 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 Albendazole 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
Albendazole is involved in metabolic pathways that lead to its transformation into metabolites: albendazole sulphoxide (ABZSO) and albendazole sulphone (ABZSO2) . These metabolites are formed in the body after administration of Albendazole .
準備方法
合成経路と反応条件
アルベンダゾールは、いくつかの経路で合成することができます。一般的な方法の1つは、2-ニトロ-5-クロロアニリンを出発物質として使用する方法です。 この化合物は、置換、縮合、還元、環化などの反応を連続的に経て、アルベンダゾールを生成します 。 このプロセスでは、高リスクの水素化還元を使用せず、代わりにアルカリ硫化物還元プロセスが採用されており、より安全で経済的です .
工業的製造方法
工業的な環境では、アルベンダゾールは、通常、混合溶媒系（水とエタノール）および混合酸系（ギ酸と酢酸）を使用して精製されます。 この方法により、純度と溶解度が高いアルベンダゾールが得られます 。 さらに、アルベンダゾールは、吸収性と有効性を高めるために、結腸標的マイクロカプセルに製剤化することができます .
化学反応の分析
反応の種類
アルベンダゾールは、酸化、還元、置換などのさまざまな化学反応を起こします。
一般的な試薬と条件
酸化: アルベンダゾールは、主に肝臓でシトクロムP450酸化酵素とフラビン含有モノオキシゲナーゼによって酸化され、アルベンダゾールスルホキシドを形成します.
主要な生成物
科学研究の用途
アルベンダゾールは、科学研究において幅広い用途があります。
化学: ベンゾイミダゾール誘導体を含む研究において、モデル化合物として使用されます。
生物学: アルベンダゾールは、駆虫薬が寄生虫およびそのライフサイクルに及ぼす影響を研究するために使用されます.
医学: 神経幼虫症や包虫症などの寄生虫感染症の治療に広く使用されています.
産業: アルベンダゾールは、溶解性、安定性、バイオアベイラビリティを向上させるために、さまざまな医薬品に製剤化されています.
類似化合物との比較
アルベンダゾールは、メベンダゾールやフェンベンダゾールなどの他のベンゾイミダゾール駆虫薬と比較されることが多いです。 3つの化合物はすべて、同様の作用機序を共有していますが、アルベンダゾールは、より広域スペクトルであり、特定の寄生虫感染症に対する有効性が高いという点でユニークです .
類似化合物
メベンダゾール: さまざまな寄生虫による感染症の治療に使用されますが、アルベンダゾールに比べてスペクトルが狭いです.
フェンベンダゾール: 主に獣医学で使用され、アルベンダゾールと同様の有効性を示します.
特性
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. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | albendazole | |
| Source | DTP/NCI | |
| 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. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the 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. | |
| 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. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | ALBENDAZOLE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/F4216019LN | |
| 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. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| 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
Procedure details
Preparation of methyl 5-propylthio-2-benzimidazole carbamate--A 1.82 g portion of cyanamide was dissolved in 10 ml of water. Methyl chloroformate, 4.64 g, and 6.34 g of 50% aqueous sodium hydroxide in 6 ml of water were added simultaneously so as to maintain the pH at approximately 7 as determined by a pH meter. The reaction mixture was stirred at 50° C. for one hour. A portion of 7.4 g of concentrated hydrochloric acid in 7 ml of water was added until the pH was 4. The methanol solution of 4-propylthio-o-phenylenediamine from Example IV was added at once. More of the hydrochloric acid solution was added to adjust the pH to 4. The reaction mixture was heated to distill the methanol. As methanol was nearly removed more hydrochloric acid solution was added to keep the pH at 4. Water was added from time to time to keep the slurry from becoming too thick. The reaction slurry was heated at 100° C. for one hour after the methanol had been removed. The reaction slurry was cooled, filtered and washed liberally with water. The solids were air dried to produce 8.77 g of crude methyl 5-propylthio-2-benzimidazole carbamate. The crude solids were washed 3 times with cold acetone and dried to produce 7.52 g of product assaying 97% methyl-5-propylthio-2-benzimidazole carbamate by HPLC, 73% yield from the 4-propylthio-2-nitroaniline employed in Example IV.
[Compound]
Name
methyl 5-propylthio-2-benzimidazole carbamate--A
Quantity
1.82 g
Type
reactant
Reaction Step Two
Synthesis routes and methods II
Procedure details
SKOV-3 human cystadenocarcinoma cell line, obtained from the American Type Culture Collection (ATCC Accession No. HTB 77) were grown in McCoy's 5a medium with 1.5 mM L-glutamine, 100 units/ml penicillin, and 100 μg/ml streptomycin, supplemented with 10% FCS. Cells were grown to confluence and harvested by trypsinization with 0.25 mg/ml trypsin/EDTA and suspended in the medium before plating. These were then seeded (2×105) on plastic 6-well Corning culture plates. Cultures were maintained in a 37° C. incubator in a humidified atmosphere of 95% O2/5% CO2. Twenty-four hours later, the medium was removed. Subconfluent cultures were washed three times with phosphate buffer followed by incubation for 6 hours with culture medium containing various concentrations of albendazole (0, 0.1, 0.25 and 1.0 μM) dissolved in 1% ethanol. After completion of the treatment period, medium from the wells were individually collected and analysed for the VEGF concentration using an enzyme-linked immunosorbant assay (ELISA) that detects soluble VEGF121 and VEGF165 isoforms (Quantikine R&D systems, Minneapolis, USA).
[Compound]
Name
5a
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
streptomycin
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Name
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
Reactant of Route 1
Reactant of Route 1
Reactant of Route 1
Albendazole
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Reactant of Route 2
Albendazole
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Albendazole
Reactant of Route 4
Reactant of Route 4
Albendazole
Reactant of Route 5
Reactant of Route 5
Albendazole
Reactant of Route 6
Reactant of Route 6
Albendazole
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