Ethosuximide
货号:
B1671622
CAS 编号:
77-67-8
分子量:
141.17 g/mol
InChI 键:
HAPOVYFOVVWLRS-UHFFFAOYSA-N
注意:
仅供研究使用。不适用于人类或兽医用途。
概述
描述
乙琥胺是一种主要用于治疗失神性癫痫（一种癫痫类型）的药物。 它属于琥珀酰亚胺类抗惊厥药，以其在控制癫痫发作而不引起明显肝毒性而闻名 。 乙琥胺口服给药，通常耐受性良好，常见的副作用包括食欲下降、腹痛和疲劳 .
作用机制
乙琥胺通过阻断大脑中的T型电压门控钙通道发挥作用 。这些通道在产生神经元中的节律性电活动中起着至关重要的作用。 通过抑制这些通道，乙琥胺减少了导致癫痫发作的异常放电 。 乙琥胺的主要分子靶点是T型钙通道的α1G亚基 .
生化分析
Biochemical Properties
Ethosuximide exerts its effects by interacting with T-type voltage-sensitive calcium channels . These channels mediate the entry of calcium ions into excitable cells and are involved in various calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division, and cell death .
Cellular Effects
This compound influences cell function by suppressing the paroxysmal three-cycle per second spike and wave activity associated with lapses of consciousness, which is common in absence (petit mal) seizures . The frequency of epileptiform attacks is reduced, apparently by depression of the motor cortex and elevation of the threshold of the central nervous system to convulsive stimuli .
Molecular Mechanism
The molecular mechanism of this compound involves the antagonism of the postsynaptic T-type voltage-gated calcium channel . This action reduces the low threshold T-type calcium currents in thalamic neurons, which are involved in the spontaneous pacemaker oscillatory activity of thalamocortical circuitry .
Temporal Effects in Laboratory Settings
It is known that this compound is rapidly absorbed with a bioavailability of >90% . Its volume of distribution is 0.7 L/kg, and plasma protein binding is 0% .
Dosage Effects in Animal Models
In animal models, this compound has shown powerful analgesic effects through the blockade of T-type voltage-gated calcium currents in sensory neurons
Metabolic Pathways
Approximately 80% of this compound undergoes hepatic metabolism, mediated primarily by cytochrome P450 isoenzymes, with a major contribution from CYP3A and, to a lesser extent, from CYP2E and CYP2C/B . The remainder, around 20% of an administered dose of this compound, is excreted unchanged in the urine .
Transport and Distribution
After oral ingestion, this compound is rapidly absorbed with a Tmax of 1–4 hours . Its volume of distribution is 0.7 L/kg, indicating that it is distributed throughout the body .
准备方法
乙琥胺可以通过多种方法合成。 一种常见的合成路线是乙酰乙酸乙酯与甲胺反应生成3-乙基-3-甲基-2,5-吡咯烷二酮 。反应条件通常包括在合适溶剂存在下，将反应物在回流状态下加热。 工业生产方法通常采用类似的合成路线，但规模更大，并增加纯化步骤以确保最终产品符合药典标准 .
化学反应分析
乙琥胺会发生多种类型的化学反应，包括：
氧化： 乙琥胺可以被氧化成各种代谢产物，主要通过肝脏中细胞色素P450酶的作用.
还原： 虽然还原反应不太常见，但在特定条件下，乙琥胺会发生还原反应，生成不同的产物。
这些反应中常用的试剂包括过氧化氢等氧化剂和硼氢化钠等还原剂。 这些反应形成的主要产物取决于所用条件和试剂的具体情况 .
科学研究应用
乙琥胺在科学研究中有着广泛的应用：
相似化合物的比较
属性
IUPAC Name |
3-ethyl-3-methylpyrrolidine-2,5-dione |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HAPOVYFOVVWLRS-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCC1(CC(=O)NC1=O)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C7H11NO2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID7023019 |
Source
|
| Record name | Ethosuximide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7023019 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
141.17 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 | Ethosuximide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014731 | |
| 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 |
Freely soluble in water, VERY SLIGHTLY SOL IN SOLVENT HEXANE, 1.01e+02 g/L |
Source
|
| Record name | Ethosuximide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00593 | |
| 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 | ETHOSUXIMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1119 | |
| 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 | Ethosuximide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014731 | |
| 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 |
Binds to T-type voltage sensitive calcium channels. Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1G gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by mibefradil. A particularity of this type of channels is an opening at quite negative potentials and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes., Succinimide anticonvulsants are thought to increase the seizure threshold and suppress the paroxysmal three-cycle-per-second spike-and-wave pattern seen with absence (petit mal) seizures. The frequency of attacks is reduced by depression of nerve transmission in the motor cortex. These effects may be due to direct modification of membrane function in excitable cells and/or alteration of chemically mediated neurotransmission. The specific effect of ethosuximide against absence seizures appears to be due to its ability to block T-type calcium channels at concentrations that do not affect other ion channels. /Succinimide Anticonvulsants/, Ethosuximide reduces low threshold Ca(2+) currents (T currents) in thalamic neurons. The thalamus plays an important role in generation of 3 Hz spike-wave rhythms typical of absence seizures. Neurons in the thalamus exhibit a large amplitude T current spike that underlies bursts of action potentials and likely plays an important role in thalamic oscillatory activity such as 3 Hz spike-wave activity. At clinically relevant concentrations, ethosuximide inhibits the T current, as evident in voltage-clamp recordings in acutely isolated, ventrobasal thalamic neurons from rats and guinea pigs. Ethosuximide reduces this current without modifying the voltage dependence of steady-state inactivation or the time course of recovery from inactivation. By contrast, succinimide derivatives with convulsant properties do not inhibit this current. Ethosuximide does not inhibit sustained repetitive firing or enhance GABA responses at clinically relevant concentrations. Current data are consistent with the idea that inhibition of T currents is the mechanism by which ethosuximide inhibits absence seizures., Ethosuximide is an alternative medicament that is used for coupling of petit mal, especially in childhood. Some clinical observations show that it has secondary effects on the gastro intestinal tract (GIT). The present research tries to define the characteristics of Ethosuximide--the inducted secondary effects on the GIT, and to explain some of the possible mechanisms that cause them. The changes that occur in the GIT of patients cured with Ethosuximide are registered roentgenologically. The main change is the atony of the stomach and intestines and the reduced peristaltic activity. The influence of Ethosuximide is examined on smooth muscular samples of human stomach, taken in vitro using stomach resection. The medicament authoritatively reduce the spontaneous bioelectrical activity of the smooth muscular tissue, influences mainly it's components that have Ca+ nature. Together with that is indicated relaxation of the smooth muscular samples. In that research is expressed the thesis that this Ethosuximide reduction of the Ca(+)-influx in the smooth muscular cells and the related relaxation probably are one of the main reasons of the secondary effects on the GIT., Ethosuximide is one of the means of treatment of minor epilepsy but hardly any data on its mechanism of action are available in the literature. Anticonvulsant agents are known to bring about changes in the functions and in the interaction between some of the mediator systems within the central nervous system. An assessment of the status of neuromediator systems can be made on the basis of the response of isolated smooth muscle strips to the action of agonists and antagonists of various receptors. It was found by the pharmacological analysis of isolated strips from the rat stomach (antrum and corpus strips), the seminal duct and the cervical vein that ethosuximide induces a reduction in the physical contractile activity and the tone of smooth muscle preparations. Smooth muscle relaxation caused by ethosuximide is not blocked by different receptor inhibitors such as dihydroergotamine, propranolol, atropine, chlorpromazine, haloperidol and indomethacin. Ethosuximide causes a significant reduction in the physical contraction of smooth muscles produced by potassium chloride depolarization, with a stronger impact on the subsequent tonic contraction caused by calcium ions. A reduction in the potassium content of the solution has no effect on the nature of the action of ethosutimide. It is thus assumed that the probable mechanism of action of ethosuximide consists in lowering calcium transport since the inhibitors of calcium transport sodium nitroprusside and verapamil intensify the blocking effect of ethosuximide on smooth muscle contractile activity. |
Source
|
| Record name | Ethosuximide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00593 | |
| 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 | ETHOSUXIMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1119 | |
| 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 |
Crystals from acetone and ether, WHITE TO OFF-WHITE CRYSTALLINE POWDER OR WAXY SOLID | |
CAS No. |
77-67-8 |
Source
|
| Record name | Ethosuximide | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=77-67-8 | |
| 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. | |
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| Record name | Ethosuximide [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000077678 | |
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| Record name | Ethosuximide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00593 | |
| 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 | ethosuximide | |
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| Record name | ethosuximide | |
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| Record name | Ethosuximide | |
| Source | EPA DSSTox | |
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| Record name | Ethosuximide | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.000.954 | |
| 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 | ETHOSUXIMIDE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/5SEH9X1D1D | |
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| Record name | ETHOSUXIMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1119 | |
| 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 | Ethosuximide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014731 | |
| 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 |
64 - 65 °C, 64.5 °C |
Source
|
| Record name | Ethosuximide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00593 | |
| 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 | ETHOSUXIMIDE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1119 | |
| 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 | Ethosuximide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014731 | |
| 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
Procedure details
To a slurry of 92.1 milligrams (mg) of the HCl salt of N-(4-aminobutyl)2-ethyl-2-methylsuccinimide in 0.6 mL of dry DMF at room temperature under argon was added 107 microliters (μL) of triethylamine. The suspension was stirred 15 min; then a solution of 180.2 mg of carbonyldiimidazole (CDI) in 0.6 mL of DMF was added via syringe in one portion. The resulting suspension was stirred at room temperature for 50 min to complete formation of the imidazole. It was then added dropwise, over 8 min, to a stirring solution of 250 mg of Miles Pentex® crystalline bovine serum albumin (BSA) (Miles Laboratories, Inc., Elkhart, IN, USA) in 108 mL of water at pH 4.5 and 5° C. The pH was maintained at 4.5 during and after the addition by an automatic titrator (HCl). After 18 hrs at pH 4.5 and 5° C., the clear, translucent reaction was adjusted to pH 8 with sodium hydroxide solution, and applied to a 3.0×62 cm column of Sephadex G-25F gel (Pharmacia, Piscataway, NJ, USA) in 50 millimolar (mM) TRIS buffer [tris(hydroxymethyl)aminomethane], pH 8.2. The column was eluted with this buffer at a flow rate of 1 mL/min and 10 mL fractions were collected.
Quantity
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
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| 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
Ethosuximide
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Reactant of Route 2
Ethosuximide
Reactant of Route 3
Ethosuximide
Reactant of Route 4
Ethosuximide
Reactant of Route 5
Ethosuximide
Reactant of Route 6
Ethosuximide
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