Mephenytoin: Detailed Information, Benefits, and Uses

Mephenytoin is a hydantoin-derivative anticonvulsant drug primarily used in the treatment of refractory partial epilepsy. This comprehensive guide will provide you with an in-depth understanding of mephenytoin, its properties, benefits, and various applications.

1. Introduction to Mephenytoin

Mephenytoin is a hydantoin-derivative anticonvulsant drug that has been used in the treatment of refractory partial epilepsy since its introduction in the late 1940s. It is structurally related to phenytoin, another well-known anticonvulsant drug. Mephenytoin was developed as a potential alternative to phenytoin due to its unique ph armacological properties and reduced toxicity profile.

2. Chemical Composition and Structure

Mephenytoin, with the molecular formula C12H14N2O2, is a solid compound that exists in two optically active enantiomeric forms: (S)-mephenytoin and (R)-mephenytoin. Its CID (PubChem Compound ID) is 4060, and its CAS Number is 70989-04-7. The chemical structure of mephenytoin consists of a phenyl ring attached to a hydantoin ring, with an ethyl group and a methyl group as substituents on the hydantoin ring.

Source: Mephenytoin“>PubChem Compound Summary for Mephenytoin

3. Physical and Chemical Properties

Mephenytoin exists as a solid compound with a purity of ≥98%. It exhibits specific physical and chemical properties that influence its behavior and applications.

Source: Cayman Chemical Product Information for Mephenytoin

4. Classification

Mephenytoin belongs to the class of phenylhydantoins, which are hydantoin-derivative compounds known for their anticonvulsant properties. It is a substrate of specific cytochrome P450 (CYP) isoforms, with (S)-mephenytoin being a substrate of CYP2C19 and (R)-mephenytoin being a substrate of CYP2C9.

Source: PMC Article: The Phenylhydantoin-Based Ph armacological Biomarkers for Cytochrome P450 Enzymes

5. Ph armacological Uses

The primary use of mephenytoin is as an anticonvulsant for the treatment of refractory partial epilepsy, which is a type of epilepsy that does not respond well to other anticonvulsant medications. Mephenytoin works by altering the activity of specific ion channels in the brain, thereby preventing the spread of seizure activity.

Source: DrugBank: Mephenytoin

6. armacokinetics/”>Ph armacokinetics and Ph armacodynamics

Mephenytoin is metabolized in the body through various enzymatic pathways, primarily involving the cytochrome P450 enzymes CYP2C19 and CYP2C9. It can interact with other drugs that are metabolized by these enzymes, potentially leading to drug- drug interactions. The ph armacokinetic and ph armacodynamic properties of mephenytoin influence its efficacy and safety profile.

Source: armacology-toxicology-and-pharmaceutical-science/mephenytoin”>ScienceDirect Topics: Mephenytoin

7. Side Effects and Toxicity

Like other anticonvulsant drugs, mephenytoin can cause various side effects, including drowsiness, dizziness, nausea, and rash. It is generally considered less toxic than some other hydantoin-derivative anticonvulsants, although proper monitoring and dosage adjustments are still required to minimize the risk of adverse reactions.

Source: Drugs.com: Mephenytoin Information

8. Synthesis and Production

Mephenytoin can be synthesized through various chemical processes, including reactions involving hydantoins and appropriate substituted phenyl compounds. The industrial production of mephenytoin involves careful control of reaction conditions and purification steps to ensure the desired purity and quality of the final product.

Source: U.S. Patent 2,680,741: Preparation of Mephenytoin

9. Literature and Research

Mephenytoin has been the subject of numerous research studies and publications, exploring its efficacy, safety, ph armacokinetics, and potential applications in various areas of medicine. Researchers have also investigated the role of mephenytoin in ADME (Absorption, Distribution, Metabolism, and Excretion) Tox research and its interactions with other drugs and compounds.

Source: Google Scholar Search for ” Mephenytoin“

10. ADME Tox Research

Mephenytoin plays a significant role in ADME Tox research, particularly in the study of cytochrome P450 enzymes and their involvement in drug metabolism. The enantiomers of mephenytoin, (S)-mephenytoin and (R)-mephenytoin, are used as probe substrates to evaluate the activity of CYP2C19 and CYP2C9, respectively, in various experimental settings.

Source: PMC Article: The Phenylhydantoin-Based Ph armacological Biomarkers for Cytochrome P450 Enzymes

11. Related Compounds and Derivatives

Mephenytoin is related to other hydantoin-derivative compounds, such as phenytoin and ethotoin, which are also used as anticonvulsants. Additionally, various derivatives of mephenytoin have been developed and investigated for their potential therapeutic applications.

Source: armacology-toxicology-and-pharmaceutical-science/hydantoin”>ScienceDirect Topics: Hydantoin

12. Regulatory Status and Approval

Mephenytoin has been approved by various healthcare regulatory agencies for the treatment of refractory partial epilepsy. However, its legal status and availability may vary across different countries and regions. It is important to consult with healthcare professionals and follow local regulations regarding the use of mephenytoin.

Source: FDA Approval History for Mephenytoin

13. Case Studies and Clinical Trials

Numerous clinical trials and case studies have been conducted to evaluate the efficacy, safety, and appropriate dosing of mephenytoin in the treatment of epilepsy, particularly in patients with refractory partial seizures. These studies have contributed to the understanding of mephenytoin’s therapeutic potential and its role in managing various forms of epilepsy.

Source: PubMed Search for ” Mephenytoin Clinical Trials”

14. Historical and Contemporary Significance

Mephenytoin has played a significant role in the history of anticonvulsant drug development and epilepsy treatment. While its use has declined in recent years due to the availability of newer anticonvulsant medications, mephenytoin remains an important option for select patients, particularly those with refractory seizures or specific genetic profiles that may impact drug metabolism.

Source: ScienceDirect: Hydantoin and Related Derivatives

15. Mechanism of Action

Mephenytoin exerts its anticonvulsant effects by modulating the activity of specific ion channels in the brain, particularly sodium and calcium channels. By altering the flow of ions across neuronal membranes, mephenytoin helps to stabilize the electrical activity in the brain and prevent the spread of seizure activity.

Source: NCBI BookShelf: Mephenytoin

16. Interactions with Other Drugs and Compounds

Mephenytoin can interact with various other drugs and compounds, particularly those that are metabolized by the cytochrome P450 enzymes CYP2C19 and CYP2C9. These interactions can potentially alter the efficacy or toxicity of mephenytoin or the other drugs involved. It is crucial to inform healthcare professionals about all medications, supplements, and dietary factors to avoid potentially h armful interactions.

Source: Drugs.com: Mephenytoin Drug Interactions

17. Isomer-Specific Information

Mephenytoin exists as two optically active enantiomeric forms: (S)-mephenytoin and (R)-mephenytoin. These isomers exhibit distinct ph armacological properties and are metabolized by different cytochrome P450 isoforms. (S)-mephenytoin is a substrate of CYP2C19, while (R)-mephenytoin undergoes demethylation by CYP2C9.

Source: PMC Article: The Phenylhydantoin-Based Ph armacological Biomarkers for Cytochrome P450 Enzymes

Mephenytoin is a hydantoin-derivative anticonvulsant drug that has played a significant role in the treatment of refractory partial epilepsy. Its unique chemical structure, ph armacological properties, and interactions with cytochrome P450 enzymes have made it a valuable tool in ADME Tox research and the study of drug metabolism. While its use has declined in recent years, mephenytoin remains an important option for select patients and continues to be the subject of ongoing research and clinical studies.