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Meglumine

Meglumine, chemically known as N-methyl-D-glucamine, is a sugar alcohol derived from D-glucose via reductive amination with methylamine, resulting in a compound with the molecular formula C₇H₁₇NO₅ and a molecular weight of 195.21 g/mol.^[1]^[2] It appears as a white, crystalline powder that is freely soluble in water, making it suitable for pharmaceutical formulations.^[2] This amino sugar serves primarily as an excipient in drug preparations, enhancing solubility and stability, particularly in ionic contrast media used for diagnostic imaging.^[1]^[2] In medical applications, meglumine is a key component in iodinated contrast agents, such as diatrizoate meglumine and iodipamide meglumine, which are administered intravascularly to visualize blood vessels, organs, and tissues during procedures like X-rays and computed tomography (CT) scans.^[1]^[2] These formulations leverage meglumine's ability to form soluble salts with organic acids, improving the delivery of radiopaque materials while minimizing osmotic effects.^[3] Additionally, meglumine is integral to antiprotozoal drugs like meglumine antimoniate, a pentavalent antimony compound used to treat leishmaniasis, a parasitic infection caused by Leishmania species that manifests in forms such as cutaneous, mucocutaneous, and visceral disease.^[4] In this context, meglumine acts as a counterion to facilitate the administration of the active antimony moiety via intravenous or intramuscular injection, typically dosed at 20 mg of pentavalent antimony per kg of body weight daily for 20–28 days under medical supervision.^[4] Beyond diagnostics and antiparasitic therapy, meglumine's role as a non-toxic, biocompatible base extends to other gadolinium-based contrast agents, such as gadoterate meglumine, employed in magnetic resonance imaging (MRI) to enhance visibility of abnormalities in the brain, spine, and other tissues.^[5] Its pharmacological inertness and low allergenicity contribute to its widespread adoption in these applications, though careful monitoring is required in patients with renal impairment due to potential risks associated with contrast media.^[3]^[5]

Chemical Properties

Molecular Structure

Meglumine, also known as N-methyl-D-glucamine, is an organic compound classified as a sugar alcohol derivative with a linear polyhydroxy chain modified by a secondary amine group. Its molecular structure consists of a six-carbon backbone resembling glucitol, where the terminal hydroxymethyl group at position 1 is replaced by a methylamino group (-CH₂-NH-CH₃), forming a secondary amine. This modification results in five hydroxyl groups attached to the carbon chain, contributing to its polyol nature, while the nitrogen atom bonds to the C1 methylene group and a methyl substituent, creating a flexible, hydrophilic molecule primarily existing in an open-chain form due to the absence of a carbonyl group necessary for cyclization.^[6] The chemical formula of meglumine is C₇H₁₇NO₅, and its molecular weight is 195.21 g/mol.^[6]^[7] The IUPAC name is 1-deoxy-1-(methylamino)-D-glucitol, reflecting its derivation from D-glucitol with the deoxy and amino substitution at C1.^[6] In structural terms, the open-chain representation can be depicted as HOCH₂-(CHOH)₄-CH₂-NH-CH₃, with the hydroxyl groups on carbons 2 through 6 providing multiple sites for hydrogen bonding.^[8] Regarding stereochemistry, meglumine exhibits the D-isomer configuration at its four chiral centers (C2, C3, C4, and C5), inherited from natural D-glucose, with specific absolute configurations designated as (2R,3R,4R,5S). This stereoisomeric form ensures the spatial arrangement of hydroxyl groups mirrors that of D-glucitol, influencing its interactions in biological and pharmaceutical contexts.^[6]^[8] Meglumine is a modified derivative of D-glucose, where reduction of the aldehyde to an alcohol and subsequent amination occur at the anomeric carbon.^[6]

Physical Characteristics

Meglumine appears as a white to off-white crystalline powder, often described as odorless or with a faint odor.^[9] This form is typical under standard conditions and contributes to its utility in pharmaceutical formulations where purity and visual consistency are essential.^[10] The compound has a melting point ranging from 129 to 131.5 °C, indicating thermal stability suitable for processing in solid dosage forms.^[11] Its estimated boiling point is approximately 331.88 °C, while the density is around 1.2669 g/cm³, both values derived from computational estimates that align with experimental observations for similar sugar amines.^[11] Meglumine exhibits high solubility in water, dissolving to approximately 10 g per 100 mL at 25 °C, which stems from its glucose-derived structure rich in hydroxyl groups.^[12] It is soluble in alcohol, such as ethanol, but insoluble in non-polar solvents like diethyl ether and chloroform. Additionally, meglumine is hygroscopic, readily absorbing moisture from the air, which necessitates controlled storage conditions to maintain its physical integrity.^[9]

Chemical Reactivity

Meglumine exhibits basic character primarily due to its secondary amine group, with a pKa value of 9.39 measured in water at 30°C and ionic strength 0.05 (N₂ atmosphere).^[9] This property enables it to act as a counterion in reactions with acids, forming stable meglumine salts that enhance solubility of acidic compounds, such as iodinated organic acids used in contrast media.^[9] The amine's nucleophilic nature facilitates protonation in acidic environments, leading to salt formation without significant side reactions under ambient conditions.^[13] Under normal storage and handling conditions, meglumine remains chemically stable, showing no tendency to polymerize or dehydrate.^[9] However, it is hygroscopic, readily absorbing moisture from the air, which can affect its handling and require sealed storage to maintain purity.^[14] Additionally, meglumine is air-sensitive, potentially undergoing slow oxidation or degradation upon prolonged exposure to atmospheric oxygen.^[14] Thermal stability is maintained up to approximately 150°C, beyond which prolonged heating leads to decomposition, releasing volatile products.^[9] Meglumine demonstrates incompatibility with certain metals, notably reacting with aluminum to evolve hydrogen gas, which poses safety risks in storage or processing.^[9] This reaction arises from the reductive action of the amine on aluminum surfaces in the presence of moisture, generating hydrogen and potentially compromising container integrity.^[15] Consequently, aluminum containers are contraindicated, with recommendations favoring inert materials like glass or stainless steel to avoid such interactions.^[9]

Synthesis and Production

Laboratory Synthesis

Meglumine, also known as N-methyl-D-glucamine, is synthesized in laboratory settings primarily through the reductive amination of D-glucose with monomethylamine. This involves the initial formation of an imine by reacting D-glucose with monomethylamine, followed by catalytic hydrogenation of the imine intermediate to yield the amine product.^[16] The reaction is typically performed in aqueous or alcoholic media using catalysts such as Raney nickel. In a representative procedure, a reactor is charged with Raney nickel (15 wt% relative to D-glucose) suspended in water, followed by addition of D-glucose (45 g as 40% aqueous solution) and monomethylamine (15.37 g as 40% aqueous solution) at 10°C. Hydrogenation proceeds under 300-500 PSI pressure with stepwise heating: 35°C for 18 hours, 50°C for 1 hour, 75°C for 1 hour, and 100°C for 1 hour, resulting in a 62.5% yield of meglumine with 99% purity by GC analysis. Yields are generally high due to the stereospecific reduction, which preserves the chiral centers from D-glucose to form the D-glucitol backbone.^[16] Alternative routes employ direct reductive amination of D-glucose with methylamine using supported nickel catalysts, such as Ni impregnated on hypercrosslinked polystyrene (25 wt% loading) in methanol solvent. These conditions involve 120°C, 40-60 bar H₂ pressure, and 0.8-1.6 mol/L glucose concentration, achieving over 99% conversion with initial activity of 1.3 kg glucose per kg catalyst per hour. Purification of the crude product entails filtration to remove the catalyst, followed by evaporation of the solvent under reduced pressure to form a viscous residue. The residue is then dissolved in hot methanol or a water-methanol mixture (e.g., 1:2 weight ratio of meglumine to solvent), cooled to 1-7°C to induce crystallization, filtered, and washed to isolate the D-isomer. Subsequent drying at 78-98°C yields high-purity meglumine (up to 99.7% by HPLC) with recovery rates around 97%.^[17]

Industrial Methods

Meglumine is produced on an industrial scale through the reductive amination of D-glucose with methylamine. D-glucose, the primary starting material, is derived from the enzymatic hydrolysis of starch sources such as corn, a common process in the food and chemical industries. Methylamine is obtained via the catalytic reaction of methanol and ammonia over metal oxide catalysts, a standard method in the petrochemical sector.^[18]^[19] The production process involves an initial condensation step where D-glucose reacts with methylamine in an alcoholic solvent, such as ethanol, to form an imine intermediate (Schiff's base). This is followed by catalytic hydrogenation in large reactors, typically using supported nickel catalysts like Raney nickel or skeletal nickel under controlled temperature (40-50°C) and pressure (0.3-0.35 MPa) conditions with hydrogen gas. The reaction mixture is then filtered to remove the catalyst, and the product undergoes crystallization, centrifugation, and drying to isolate meglumine. This approach scales up the basic imination-hydrogenation route used in laboratory settings.^[16]^[20]^[21] Industrial yields for meglumine production typically exceed 90%, with optimized processes reporting ranges of 87-97% based on glucose input. The crude product is purified through crystallization in solvents like methanol or water, often aided by chelating agents such as disodium EDTA to remove impurities, achieving pharmaceutical-grade purity suitable for excipient use. Ion-exchange resins may also be employed in some purification sequences to ensure low levels of residual metals and solvents.^[20] Environmental considerations in meglumine production focus on sustainability, with water- or solvent-based reaction media designed to minimize waste generation. Catalysts like skeletal nickel are recyclable, allowing multiple uses and reducing the need for fresh materials, while solvent recovery systems help limit emissions and effluent discharge. These practices align with green chemistry principles to lower the overall ecological footprint of large-scale operations.^[20]

Pharmaceutical Applications

Role in Contrast Media

Meglumine functions primarily as a cationic counterion in ionic iodinated contrast media, pairing with anionic iodinated organic acids such as benzoic acid derivatives to form stable, water-soluble salts essential for diagnostic imaging.^[22] This formulation approach improves the aqueous solubility of the otherwise poorly soluble iodinated compounds, enabling their preparation at concentrations suitable for safe intravenous delivery.^[23] In these formulations, meglumine contributes to osmolality control by balancing the ionic strength of the solution, which helps mitigate hyperosmolar effects that could otherwise lead to discomfort or hemodynamic instability during procedures.^[22] Its inherent low toxicity profile further enhances patient tolerability, as the meglumine salt reduces chemotoxicity compared to alternatives like sodium salts, allowing for better overall safety in clinical use.^[23] Prominent examples of meglumine-containing contrast agents include diatrizoate meglumine and iothalamate meglumine, which are administered intravenously to visualize blood vessels and the brain in angiography and cerebral studies, respectively; and iodipamide meglumine, used for outlining the gallbladder in cholecystography.^[24]^[25] These agents provide high radiographic density due to their iodine content, facilitating clear imaging of targeted anatomical structures.^[26] Meglumine-based ionic contrast media gained widespread adoption in the mid-20th century, starting in the 1950s, as they represented a significant advancement in water-soluble agents for X-ray diagnostics, remaining staples until non-ionic formulations emerged in the 1970s. Although non-ionic agents have largely supplanted them due to improved safety profiles, meglumine-based ionic media remain available for specific indications as of 2025.^[22]

Use in Antiprotozoal Agents

Meglumine serves as a key component in the formulation of meglumine antimoniate, commercially known as Glucantime, a pentavalent antimony compound that functions as a primary therapeutic agent for leishmaniasis. This drug targets cutaneous, mucocutaneous, and visceral forms of the disease caused by protozoan parasites of the genus Leishmania.^[27] The compound is prepared through the salt-forming reaction of meglumine with pentavalent antimony, yielding a water-soluble complex suitable for parenteral administration.^[28] Meglumine antimoniate is typically administered by intramuscular or intravenous injection at a dosage of 20 mg of pentavalent antimony per kg of body weight daily, with treatment courses lasting 20 to 28 days depending on the clinical form and severity of leishmaniasis.^[4] This regimen has demonstrated clinical efficacy against multiple Leishmania species, with cure rates ranging from 80% to 90% in responsive cases, particularly for uncomplicated cutaneous lesions.^[29] However, increasing reports of resistance in certain Leishmania strains have been associated with treatment failures as of 2024.^[30] The antiprotozoal action primarily involves the intracellular delivery of antimony to the parasites, where it disrupts essential redox processes by inhibiting trypanothione reductase and inducing oxidative stress through reactive oxygen species generation.^[31] In practice, meglumine antimoniate is the preferred antimonial in endemic regions including Latin America and the Middle East, where it is widely available through public health systems for managing leishmaniasis outbreaks.^[32] It serves as a key alternative to sodium stibogluconate, offering comparable efficacy with potentially fewer injection-site reactions in certain populations.^[33]

Other Excipient Functions

Meglumine functions as a counterion in salt formation to enhance the solubility of poorly water-soluble active pharmaceutical ingredients (APIs), thereby improving their bioavailability in oral and parenteral formulations. This role is particularly valuable for weakly acidic drugs, where meglumine's basic properties facilitate the creation of more soluble complexes without compromising stability. For instance, in combination with cyclodextrins, meglumine has been shown to boost the aqueous solubility of certain new chemical entities through synergistic interactions, leading to enhanced dissolution rates and pharmacokinetic profiles.^[34] Recent examples include tafamidis meglumine (Vyndaqel), approved in 2019 for treating transthyretin amyloid cardiomyopathy, where it enhances the solubility of the active ingredient.^[35] In addition to solubility enhancement, meglumine contributes to formulation stability and pH adjustment, serving as a buffering agent in injectables and oral dosage forms to maintain optimal pH ranges and prevent degradation. Its polyhydroxy structure allows for mild alkalinity, which helps stabilize sensitive APIs during storage and administration. An example is its use in gadoterate meglumine formulations for MRI contrast, where it supports a pH of 6.5 to 8.0 and enhances the overall thermodynamic stability of the gadolinium complex.^[36]^[37] Meglumine also plays a key role in veterinary pharmaceuticals, notably as the counterion in flunixin meglumine injections, which improve the solubility and thus the efficacy of the non-steroidal anti-inflammatory drug for treating musculoskeletal disorders, colic, and endotoxemia in horses and cattle. This application leverages meglumine's ability to enable rapid intravenous delivery while ensuring compatibility with animal physiology.^[38]^[39] Beyond human and veterinary medicines, meglumine acts as an excipient in topical and cosmetic products to improve skin compatibility, solubility of active ingredients, and formulation texture. In advanced delivery systems like ionic liquids or liquid crystalline gels, it facilitates enhanced permeation through the skin barrier, supporting treatments for dermatological conditions while minimizing irritation due to its biocompatible nature.^[40]^[41]

Pharmacology and Safety

Pharmacological Profile

Meglumine, when administered intravenously as part of pharmaceutical formulations such as contrast media, is rapidly introduced into the systemic circulation, achieving immediate bioavailability without significant absorption barriers.^[42] Its high water solubility facilitates widespread distribution throughout the extracellular fluid spaces, including both intravascular and interstitial compartments, with rapid equilibration occurring within minutes of injection.^[43] In formulations such as gadoterate meglumine, the agent exhibits minimal binding to plasma proteins (less than 3%), which further promotes its free diffusion and limits sequestration in tissues.^[43] Meglumine undergoes negligible metabolism in the body, with no evidence of significant biotransformation such as N-demethylation or oxidation, as demonstrated in early radiolabeled studies.^[44] It is primarily excreted unchanged via the kidneys through glomerular filtration; in contrast media formulations like diatrizoate, approximately 99% of elimination occurs renally, with a small fraction (about 1%) cleared through hepatic and biliary routes.^[45] The renal clearance follows a biphasic pattern, with the majority (over 80%) eliminated within the first 4 hours post-administration, reflecting its extracellular distribution and lack of reabsorption.^[42] As an excipient, meglumine does not produce direct pharmacological effects but enhances drug delivery by forming salts that improve solubility and stability, such as in iodinated contrast media where it serves as a counterion to reduce overall solution hypertonicity compared to sodium-only formulations.^[13] This modulation helps mitigate osmotic imbalances during administration without altering the primary active agent's activity. Some preclinical studies have suggested mild protective bioactivity, including improved glycemic control, reduced triglycerides, and enhanced muscle function in models of metabolic syndrome and type II diabetes, though these effects remain unestablished in clinical settings.^[46]

Toxicity and Adverse Effects

Meglumine demonstrates low acute toxicity across various administration routes. The oral LD50 exceeds 5,000 mg/kg in both rats and rabbits, indicating minimal risk from ingestion.^[47]^[14] Intravenous administration also shows low toxicity (LD50 >14,000 mg/kg in rat formulations), supporting its safety as a pharmaceutical excipient.^[48] Handling meglumine powder can cause mild adverse effects, including skin irritation (H315), serious eye irritation (H319), and respiratory tract irritation (H335).^[49] In pharmaceutical formulations, rare allergic reactions have been reported, such as delayed hypersensitivity at injection sites with meglumine antimoniate or anaphylactic shock with gadoterate meglumine contrast agents.^[50]^[51] When incorporated into high-osmolality ionic contrast media, meglumine contributes to formulation-related effects stemming from elevated osmolality, including nausea, vomiting, and hypotension.^[52]^[53] In antiprotozoal agents like meglumine antimoniate, toxicity is primarily attributed to the antimony component, manifesting as cardiotoxicity (e.g., electrocardiographic abnormalities), rather than the meglumine counterion.^[54]^[55] Data on chronic exposure to meglumine are limited, with no significant long-term adverse effects reported for the compound itself, underscoring its biocompatibility as a solubilizing agent in approved medications.^[56] In contrast, chronic use of antimony-containing formulations such as meglumine antimoniate may lead to liver and kidney damage due to antimony accumulation.^[57]^[54]

Regulatory Considerations

Meglumine is classified as a safe pharmaceutical excipient by the U.S. Food and Drug Administration (FDA), where it is included in the Inactive Ingredient Database for use in injectable, oral, and topical formulations, reflecting its established safety profile in drug products.^[58] It is also officially listed in the European Pharmacopoeia as a compendial excipient, ensuring compliance with harmonized quality specifications across Europe.^[59] In terms of regulatory approvals, meglumine features prominently in several FDA-approved medications, such as diatrizoate meglumine injection, which is authorized for use as a radiographic contrast agent in gastrointestinal examinations.^[60] Additionally, meglumine antimoniate (marketed as Glucantime) is recognized on the World Health Organization's Model List of Essential Medicines for the treatment of leishmaniasis, underscoring its role in global public health initiatives for neglected tropical diseases. As of 2025, pharmacovigilance data for gadoterate meglumine after over 170 million doses confirm a favorable safety profile with rare hypersensitivity reactions and no confirmed cases of nephrogenic systemic fibrosis.^[61] Pharmaceutical-grade meglumine must meet stringent purity standards, typically exceeding 99% as specified by the United States Pharmacopeia (USP) and equivalent pharmacopeias, to ensure its suitability for medicinal applications.^[62] Storage requirements for this grade recommend refrigeration at 2-8°C to maintain stability, and it carries a GHS07 hazard pictogram indicating potential irritation to skin, eyes, and respiratory tract upon exposure.^[63] Regulatory approaches to meglumine vary globally, particularly in formulations involving antimony compounds like meglumine antimoniate, which face restrictions in regions such as the United States due to requirements for enhanced toxicity monitoring and limited availability.^[4] Veterinary applications, such as in flunixin meglumine for animal pain management, are subject to separate regulatory frameworks, including specific approvals by bodies like the European Medicines Agency for veterinary use.

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Nephrotoxicity attributed to meglumine antimoniate (Glucantime) in ...
Their most severe side effects have been reported to be increased hepatic enzyme levels and electrocardiographic abnormalities. ... Kidney Diseases / chemically ...Missing: toxicity cardiotoxicity liver
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[PDF] 210064Orig1s000 CLINICAL REVIEW(S) - accessdata.fda.gov
Oct 11, 2017 · 3. Meglumine is an amino sugar derived from sorbitol and helps to in formulation. It is an FDA approved excipient in pharmaceuticals via ...
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[PDF] R [Diatrizoate Meglumine and Diatrizoate Sodium Injection USP]
Mar 1, 2017 · Ionic iodinated contrast media inhibit blood coagulation, in vitro, more than nonionic contrast media. Nonetheless, it is prudent to avoid ...
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Meglumine CAS 6284-40-8 | 106143 - Merck Millipore
106143 SAFCMeglumine ; LD 50 oral, LD50 Rat > 5000 mg/kg ; Storage class, 10 - 13 Other liquids and solids ; WGK, WGK 1 slightly hazardous to water ; Disposal, 3