Mefloquine is a drug traditionally used to treat malaria, but research has shown it to have other potential applications, including use as an antibiotic adjuvant, antiviral, and antitumor agent .

Antibiotic Adjuvant

This compound has emerged as a promising antibiotic adjuvant because of its ability to enhance the effectiveness of conventional antibiotics against resistant bacterial strains . this compound exhibits synergistic bacteriostatic effects when combined with antibiotics, including colistin, β-lactams, antituberculosis drugs, quinolones, and linezolid . Potential mechanisms underlying these synergistic effects include the inhibition of antibiotic efflux, disruption of bacterial cell membrane integrity, and disturbance of biofilm formation .

Antiviral Effects

This compound has demonstrated antiviral activity against SARS-CoV-2 by inhibiting the viral entry process after the virus attaches to the cell . Mathematical modeling suggests that this compound administration could reduce viral dynamics in patients, reducing the cumulative viral load and shortening the period until virus elimination in clinical concentration ranges .

Antitumor Effects

This compound has demonstrated antitumor effects against several cancers .

Cancer Type	This compound Activity
Acute Myeloid Leukemia	Selectively kills acute myeloid leukemia cells and progenitor cells by disrupting lysosomes .
Melanoma and Lung Cancer	Induces tumor ferroptosis via IFN-γ-STAT1-IRF1-LPCAT3, enhancing the efficacy of anti-programmed cell death 1 (PD-1) immunotherapy .

Inhibition of Multiple Membrane Channels

This compound has been shown to inhibit multiple membrane channels . It acts as an antagonist of the cardiac potassium channel, KvLQT1/minK, and slows its activation . this compound also effectively blocks volume-regulated and calcium-activated chloride channels .

Malaria Prophylaxis

This compound is used for malaria prophylaxis in nonimmune travelers . However, atovaquone-proguanil was better tolerated than this compound and similarly effective for malaria .

Neuropsychiatric Symptoms

A case study reported the development of acute neuropsychiatric symptoms in a 10-year-old boy after returning from travel in Africa, where he had taken this compound . A 4-week course of cognitive-behavioral therapy effectively treated this substance-induced anxiety disorder caused by this compound . The study highlights the importance of obtaining travel histories, including exposure to prophylactic medication, when patients present with acute-onset psychiatric symptoms .

Long-term Neurocognitive Effects

Some case studies have reported word-finding, processing speed, verbal learning, auditory and visual memory, motor speed, and motor learning deficits as side effects of this compound use . Other case studies reported neurobehavioral/neurologic symptoms, vestibular dysfunction, and mild impairment in fine motor dexterity and processing speed . One case study reported long-term symptoms of self-reported dizziness, short-term memory, vivid dreams/nightmares, and vestibulopathy persisted .

Prolonged Visual Illusions

Prolonged visual illusions have been reported as a result of this compound use .

Babesiosis

作用機序

メフロキンの正確な作用機序は完全には解明されていません。メフロキンは、マラリア原虫ファルシパラムの80Sリボソームを標的にし、タンパク質合成を阻害し、シゾント殺効果をもたらすと考えられています . メフロキンはまた、アセチルコリンエステラーゼを阻害することによってコリン作動性シナプス伝達を変化させ、脳の神経伝達に影響を与えます .

類似の化合物との比較

メフロキンは、キノリン-メタノール系のマラリア治療薬に属します。類似の化合物には以下が含まれます。

クロロキン： 古いマラリア治療薬で、マラリア原虫の非耐性株に効果があります。

ヒドロキシクロロキン： クロロキンに似ていますが、自己免疫疾患にも使用されます。

キニーネ： 最初のマラリア治療薬ですが、現在では耐性と副作用のためにあまり使用されなくなっています.

メフロキンは、長い半減期により、毎週の投与が可能であり、クロロキン耐性株に効果があるという点でユニークです . メフロキンは、神経精神医学的な副作用も認められており、一部の人々では使用が制限されています .

類似化合物との比較

Mefloquine is part of the quinoline-methanol class of antimalarial drugs. Similar compounds include:

Chloroquine: An older antimalarial drug, effective against non-resistant strains of Plasmodium.

Hydroxychloroquine: Similar to chloroquine but with additional uses in autoimmune diseases.

Quinine: The original antimalarial drug, now less commonly used due to resistance and side effects.

This compound is unique in its long half-life, allowing for weekly dosing, and its efficacy against chloroquine-resistant strains . it is also associated with neuropsychiatric side effects, which limits its use in certain populations .

生物活性

Mefloquine is a synthetic antimalarial drug that has garnered attention for its diverse biological activities beyond its primary use in treating malaria. This article delves into the compound's mechanisms of action, its effects on various pathogens, and associated neuropsychiatric outcomes, supported by case studies and research findings.

Chemical Profile

Chemical Name : (α S)- rel-α-(2 R)-2-Piperidinyl-2,3-bis(trifluoromethyl-4-quinolinemethanol hydrochloride
Purity : ≥98%
Molecular Weight : 433.87 g/mol

This compound exhibits multiple biological activities:

Antimalarial Activity :
- This compound targets the Plasmodium falciparum 80S ribosome, inhibiting protein synthesis, which is crucial for the survival of the malaria parasite. It has shown efficacy in improving survival rates in P. berghei-infected mice .
Antischistosomal Activity :
- The compound demonstrates both in vitro and in vivo activity against Schistosoma mansoni, suggesting potential for broader parasitic infections treatment .
Antiviral Properties :
- Recent studies indicate this compound has antiviral activity against SARS-CoV-2 with an IC50 of less than 10 μM, showcasing its potential in combating viral infections .
Antifungal Activity :
- This compound derivatives have been found to possess broad-spectrum antifungal activity against resistant strains of fungi such as Candida auris, indicating a novel mechanism that could be exploited for therapeutic purposes .
Neuropharmacological Effects :
- This compound acts as a gap junction blocker (Cx36 and Cx50), influencing neuronal communication and potentially affecting neurocognitive functions .

Neuropsychiatric Outcomes

Despite its therapeutic benefits, this compound has been associated with various neuropsychiatric side effects:

A cohort study indicated that veterans exposed to this compound reported poorer health outcomes and greater neurobehavioral symptoms compared to unexposed individuals .
Commonly reported symptoms include:
- Word-finding difficulties
- Processing speed deficits
- Auditory and visual memory issues
- Dizziness and vivid dreams .

Case Studies

A selection of case studies highlights the complexities surrounding this compound's effects:

One study documented persistent symptoms such as dizziness and memory issues in a veteran population following this compound exposure, despite overall neuropsychological assessments appearing normal .
Another case highlighted vestibular dysfunction linked to this compound use, underscoring the need for careful monitoring in patients prescribed this medication .

Comparative Efficacy Against Pathogens

The following table summarizes the comparative efficacy of this compound against various pathogens:

Pathogen	Mechanism of Action	IC50/MIC Values
Plasmodium falciparum	Inhibition of protein synthesis	Not specified
Schistosoma mansoni	Disruption of metabolic processes	Not specified
Candida auris	Disruption of cell membrane integrity	Improved by 8-64 fold
Mycobacterium abscessus	Interference with mycolic acid biosynthesis	MIC = 16 μg/mL

特性

IUPAC Name	(S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2/t12-,15+/m1/s1	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	XEEQGYMUWCZPDN-DOMZBBRYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	C1CCN[C@H](C1)[C@H](C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C17H16F6N2O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID4037168, DTXSID101019853	Source
Record name	Mefloquine
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID4037168
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	(-)-Mefloquine
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID101019853
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	378.31 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Density	Crystal density: 1.432 g/cu cm	Source
Record name	MEFLOQUINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6853
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.

Mechanism of Action	Mefloquine, like chloroquine and quinine, is a blood schizonticidal agent and is active against the intraerythrocytic stages of parasite development. Similar to chloroquine and quinine, mefloquine appears to interfere with the parasite's ability to metabolize and utilize erythrocyte hemoglobin. The antimalarial activity of mefloquine may depend on the ability of the drug to form hydrogen bonds with cellular constituents; results of structure-activity studies indicate that the orientation of the hydroxyl and amine groups with respect to each other in the mefloquine molecule may be essential for antimalarial activity. While the precise mechanism of action of mefloquine is unknown, it may involve mechanisms that differ from those proposed for chloroquine., The effects of the antimalarial drug, mefloquine, on the uptake and release of Ca2+ by crude microsomes from dog brain were investigated using a spectrophotometric method. Mefloquine inhibited the inositol-1,4,5-phosphate (IP3)-induced Ca2+ release with an IC50 of 42 uM, but was a weaker inhibitor of the uptake of Ca2+ into the vesicles (IC50: 272 uM). These effects of mefloquine are in contrast to its actions on Ca2+ uptake and release by skeletal muscle microsomes, where its predominant effect was seen to be the inhibition of Ca2+ uptake into the vesicles. Mefloquine was found to be more potent than quinine as a specific inhibitor of Ca2+ release from IP3-sensitive stores in dog brain microsomes. The possibility of the drug affecting cellular IP3-linked signal transduction processes should be considered.	Source
Record name	MEFLOQUINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6853
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.

CAS No.	51742-87-1, 53230-10-7	Source
Record name	(+)-Mefloquine
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=51742-87-1
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	Mefloquine
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=53230-10-7
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	(-)-Mefloquine
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0051742871
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	Mefloquine [USAN:INN:BAN]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0053230107
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	Mefloquine
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID4037168
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	(-)-Mefloquine
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID101019853
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	MEFLOQUINE
Source	FDA Global Substance Registration System (GSRS)
URL	https://gsrs.ncats.nih.gov/ginas/app/beta/substances/TML814419R
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	MEFLOQUINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6853
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.

Melting Point	174-176 °C	Source
Record name	MEFLOQUINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6853
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.

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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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

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試験管内研究製品の免責事項と情報

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Mefloquine

概要

説明

準備方法

化学反応解析

科学研究への応用

化学反応の分析

科学的研究の応用

Antibiotic Adjuvant

Antiviral Effects

Antitumor Effects

Inhibition of Multiple Membrane Channels

Malaria Prophylaxis

Neuropsychiatric Symptoms

Long-term Neurocognitive Effects

Prolonged Visual Illusions

Babesiosis

作用機序

類似の化合物との比較

類似化合物との比較

生物活性

Chemical Profile

Neuropsychiatric Outcomes

Case Studies

Comparative Efficacy Against Pathogens

特性

IUPAC Name

InChI

InChI Key

Canonical SMILES

Isomeric SMILES

Molecular Formula

DSSTOX Substance ID

Molecular Weight

Density

Mechanism of Action

CAS No.

Melting Point

Retrosynthesis Analysis

Strategy Settings

Feasible Synthetic Routes

試験管内研究製品の免責事項と情報

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