GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.≥97%
Gabapentin enacarbil (XP-13512) is a prodrug of Gabapentin (HY-A0057) designed to be absorbed throughout the intestine by high-capacity nutrient transporters. Gabapentin is a potent P/Q type Ca2+ channel blocker. Gabapentin enacarbil can be used for the s
Storage
Protected from light,Store at -20°C,Argon charged
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No manufacturer-validated protocols are provided for this item. The following general research workflows are commonly used with small-molecule prodrugs like gabapentin enacarbil.
A) Stock solution preparation (analytical)
Weigh required amount quickly to minimize ambient moisture exposure.
Dissolve to 10–50 mM in anhydrous DMSO; vortex until clear.
Aliquot into amber vials or tubes, argon blanket, store at −20 °C.
B) LC–MS/MS quantitation (generic RP method)
Column: C18, 2.1 × 50 mm, 1.7–3 µm.
Mobile phase A: water + 0.1% formic acid (or 5–10 mM ammonium formate).
Mobile phase B: acetonitrile (or methanol) + 0.1% formic acid.
Gradient: 5%→95% B over 3–5 min; flow 0.3 mL/min; MS in positive ESI.
Prepare calibration curve from DMSO stock diluted into matrix-matched samples.
C) Enzymatic hydrolysis assay (screening)
Incubate 1–10 µM compound with plasma or microsomes (0.2–0.5 mg/mL) at 37 °C in pH 7.4 buffer.
Sample at defined times; quench with 3× volume ice-cold ACN containing internal standard.
Centrifuge, inject supernatant for LC–MS/MS to track disappearance of prodrug and appearance of gabapentin.
Adjust conditions to instrument and matrix; validate for linearity, accuracy, precision, and stability as required for your study.
Biological Roles
Context (literature; not item specifications)
Gabapentin enacarbil is a prodrug engineered to convert to gabapentin via enzymatic and, to a lesser extent, chemical hydrolysis. The promoieties increase lipophilicity and enable interaction with high-capacity intestinal transport mechanisms in model systems, which can enhance uptake in comparative studies relative to gabapentin.
Biochemical transformations
Hydrolysis: Carboxylesterases and related hydrolases cleave ester/carbonate linkages to yield gabapentin and the corresponding alcohol/carboxylate fragments. Hydrolysis rates are matrix- and species-dependent.
Ionization: The secondary amine of the gabapentin core remains basic; the masked carboxylate reduces zwitterionic character until unmasked, altering partitioning and permeability in model membranes.
Research uses informed by biology
ADME profiling: in vitro permeability, transporter engagement screening, and metabolic stability assays to compare activation to gabapentin.
Protein binding and distribution: increased lipophilicity may alter nonspecific binding; measure using equilibrium dialysis or ultrafiltration in research settings.
Enzyme kinetics: determination of kcat/KM for hydrolytic enzymes in cell fractions or purified systems to map activation pathways.
Notes
No claims are made regarding therapeutic use or efficacy. All descriptions above are for mechanistic and biochemical context to support laboratory research.
Buffer Applications
This compound is not a buffering reagent and does not serve as a primary pH buffer system. For experiments involving gabapentin enacarbil:
Choose buffers based on the biological or chemical assay (e.g., phosphate, HEPES, or ammonium formate/acetate for LC–MS compatibility).
Maintain pH conditions that minimize non-enzymatic hydrolysis if investigating enzymatic activation (avoid strong base; keep neutral to mildly acidic conditions unless base-catalyzed cleavage is the subject of study).
For detailed buffer recipes and pH ranges, consult standard buffering agents rather than this compound.
Green Alternatives
As a discrete small molecule, “greener alternatives” pertain to solvent choices and workflow design rather than replacement of the compound itself.
Greener solvent choices (general guidance)
Preferred for dissolution and chromatography
Ethanol or isopropanol: renewable content, lower toxicity than many aprotic solvents; good for intermediate dilutions if solubility allows.
Water with minimal co-solvent: where feasible for assay matrices, reduces VOC use.
Use with caution
Acetonitrile and methanol: common in LC; optimize gradients to minimize consumption and enable solvent recycling where available.
DMSO: highly effective solvency but not “green”; minimize volumes via concentrated stocks and careful aliquoting.
Small comparison (qualitative)
DMSO vs ethanol: DMSO offers higher solubility and stability; ethanol is greener but may not dissolve as much compound.
ACN vs MeOH in RP-LC: ACN often gives better peak shape; MeOH is greener but can increase backpressure—evaluate on your system.
Operational strategies
Scale down assays (microplates, microflow LC) to reduce solvent.
Implement LC methods that use aqueous-rich phases and shorter columns where resolution allows.
Capture and properly segregate solvent waste to facilitate disposal or recycling.
All guidance above is general and should be validated for your specific research protocols.
Pharmaceutical Uses
This product is supplied strictly for research use. No medical or clinical claims are made.
Relevant research/formulation contexts (general)
Reference standard: used to develop and qualify analytical methods (HPLC/UPLC/LC–MS) for drug substance/process intermediates in R&D laboratories.
Preformulation studies: assessment of solubility, pH stability, and hydrolysis kinetics; salt/form screening of the parent (gabapentin) generated upon activation.
Excipient compatibility: stress studies with common excipients (e.g., lactose, microcrystalline cellulose, PVP) to map potential interactions under heat/humidity.
Forced degradation: systematic stress (acid/base, oxidative, thermal, photolytic) to establish degradation pathways and to support stability-indicating methods.
Standards/monographs
Pharmacopeial status for gabapentin enacarbil may vary by jurisdiction and time; consult current compendia for any monographs relevant to reference or impurity standards. This listing provides no compendial certification.
Packaging/handling implications
Supplied under argon and protected from light at −20 °C, which is consistent with minimizing hydrolytic/oxidative degradation during research storage and handling.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for context; not specifications for this lot)
Physical state: typically a solid, often crystalline (literature)
Solubility profile: readily soluble in DMSO and many polar organic solvents; limited aqueous solubility compared with gabapentin due to prodrug lipophilicity (literature, qualitative). Methanol and acetonitrile generally provide good solubility for analytical work.
Lipophilicity: increased versus gabapentin (qualitative, literature), consistent with prodrug design to enhance permeability and transporter engagement.
pKa: the secondary amine of the gabapentin core is basic; apparent pKa is shifted by the prodrug masking of the carboxylate (qualitative, literature). Numerical values are method-dependent and not provided here.
Thermal points (mp/bp), density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes
Prepare analytical stocks at 10–50 mM in anhydrous DMSO for LC–MS/UPLC method development (general practice).
Filter through 0.2 µm PTFE before quantitative injections to remove particulates if preparing solutions near solubility limits.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Moligand™
What Moligand™ typically implies (general description; not a specification)
Moligand™ denotes a research-grade small-molecule offering suitable for discovery chemistry, screening, and reference applications. Emphasis is placed on structural authenticity, low residual solvents/metals consistent with small-molecule supply for medicinal chemistry, and packaging under inert atmosphere when stability warrants it.
For this item, the product is supplied argon charged and with light protection at −20 °C, indicating a focus on hydrolytic and oxidative stability.
How to use this grade effectively
Identity and purity should be verified as appropriate for your application (e.g., HPLC/UPLC purity check, 1H NMR, HRMS). If quantitative bioanalytical work is planned, establish calibration with an independently characterized reference.
UV background, water content, and residual solvent levels can affect analytical baselines and solubility; specific numeric limits are Not specified for this item; refer to CoA/Spec Sheet.
Documentation
Request and review the CoA/Spec Sheet for: lot-specific purity assay, residual solvents, water content (KF), and any stabilizers or counterions.
SDS provides authoritative hazard classification and handling guidance.
Reaction and Applications
This material is a defined small-molecule prodrug and is not typically used as a general reagent. Its research value lies in analytical, biochemical, and ADME investigations.
Applications (research use; literature-informed)
Reference standard for LC–MS/UPLC assay development and quantitation in in vitro systems (e.g., microsomes, plasma) alongside gabapentin.
Stability and hydrolysis studies across pH and enzyme sources (carboxylesterases/paraoxonases) to map prodrug activation kinetics.
Transporter interaction studies due to the enacarbil promoieties designed to engage solute carriers; useful in uptake/efflux screening panels.
Comparative permeability and solubility assessments versus parent gabapentin to elucidate prodrug design principles.
Chemical behavior (general)
Ester/carbonate functionalities undergo hydrolysis in basic media and in the presence of esterases, releasing gabapentin and corresponding alcohol/carboxylate fragments.
Amine functionality can form salts with mineral or organic acids, which may alter solubility and stability profiles (useful for formulation screening in research settings).
Practical tips
Control moisture and pH during experiments to differentiate chemical from enzymatic hydrolysis pathways.
For kinetic studies, quench aliquots rapidly (e.g., with ice-cold ACN containing formic acid) to arrest further hydrolysis prior to LC–MS analysis.
Note: No clinical or therapeutic applications are implied; for research use only.
Reaction Conditions
While not a general reagent, two experimental paradigms are common in research with gabapentin enacarbil:
Chemical hydrolysis (general guidance; literature-informed)
Purpose: generate gabapentin or study degradation pathways.
Solvents: water/organic mixtures (e.g., H2O/MeOH or H2O/ACN). For non-enzymatic pathways, maintain ionic strength with simple buffers.
pH: base-catalyzed hydrolysis proceeds more rapidly under mildly basic conditions (e.g., pH 8–10). Acidic conditions typically slow carbonate cleavage but may promote other pathways; verify experimentally.
Temperature: ambient to 40 °C to modulate rate; avoid excessive heating that can cause secondary degradations.
Workup/analysis: quench with acid and/or organic precipitation and analyze by LC–MS using RP methods.
Enzymatic hydrolysis (carboxylesterases; general guidance)
Matrix: liver microsomes, S9, cytosol, plasma, or purified esterases.
Conditions: 0.1 M phosphate or Tris buffer, pH 7.4; 37 °C; protein 0.1–1 mg/mL depending on system.
Controls: heat-inactivated matrix and buffer blanks to separate chemical from enzymatic cleavage.
Quench: ice-cold ACN with 0.1% formic acid; centrifuge and analyze supernatant by LC–MS/MS for parent/prodrug and products.
All parameters above are representative research practices from the literature and should be optimized for your specific system.
Safety and Handling
GHS/SDS
Signal word, H-statements, pictograms, and classification: Not specified for this item; refer to SDS.
General laboratory safety (non-binding guidance)
Handle in a fume hood or well-ventilated area. Avoid inhalation of dusts and contact with skin/eyes.
Recommended PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). For weighing fine powders, consider a dust mask/respirator per institutional policy.
Incompatibilities: Avoid strong acids/bases for prolonged periods (may cause ester/carbonate cleavage). Avoid strong oxidizers. Moisture may promote slow hydrolysis; keep containers tightly closed under inert gas as provided.
Special risks: As an ester/carbonate prodrug, the substance may hydrolyze to gabapentin and alcohol/carboxylate fragments under basic or enzymatic conditions. Manage pH and moisture during handling and storage.
First aid (overview; follow SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention for irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Spill/cleanup: Avoid dust generation. Collect with inert absorbent, place in suitable container for disposal. Decontaminate area with mild detergent solution.
Waste: Dispose of in accordance with local regulations as organic laboratory waste.
Always consult the product SDS for definitive hazard and response information.
Solvent Selection
Purpose: dissolution for stock solutions, analytics, and stability studies of a lipophilic prodrug.
Increased lipophilicity versus gabapentin supports good solubility in polar aprotic and many moderately polar organic solvents.
Recommended solvents (general guidance)
Primary: anhydrous DMSO (excellent solvency; preferred for bioanalytical stocks).
Secondary: acetonitrile (HPLC/UPLC mobile phases), methanol, ethanol, isopropanol.
Aqueous: typically limited intrinsic solubility; aqueous stocks are best prepared by co-solvent or pH adjustment after preparing a concentrated DMSO or MeOH intermediate.
Mobile phase compatibility
Reversed-phase LC: ACN/H2O or MeOH/H2O with 0.1% formic acid is commonly effective for MS-friendly methods; ammonium formate/acetate buffers support MS quantitation (general practice).
Comparison notes (qualitative)
DMSO: maximal solubility and stability; may require dilution to <1% v/v in bioassays.
MeOH/EtOH: good solvency; higher volatility aids evaporation for sample prep.
ACN: strong elution control in RP-LC; moderate solvency for stocks.
Practical tips
Prepare 10–50 mM stocks in dry DMSO; aliquot and store at −20 °C protected from light to minimize hydrolysis.
Avoid prolonged exposure to basic aqueous media that can accelerate ester/carbonate cleavage.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Protected from light, Store at −20 °C, Argon charged.
Shipped in: Ice chest + ice pads.
General guidance
Keep tightly sealed under inert gas (argon or nitrogen) to minimize oxidative and hydrolytic degradation. Minimize headspace and moisture ingress.
After first opening, promptly prepare aliquots to reduce repeated freeze–thaw and atmospheric exposure.
Protect from light using amber vials or foil wrapping.
Prepare concentrated stocks (e.g., 10–50 mM) in anhydrous DMSO. If aqueous working solutions are required, dilute the DMSO stock into buffer immediately before use, keeping final DMSO ≤1% v/v where biological systems are involved.
For analytical standards, allow vials to equilibrate to room temperature before opening to prevent condensation. Weigh rapidly and recap under inert gas.
Stability notes
Solution stability depends on solvent, concentration, pH, temperature, and light. Monitor by LC–MS or HPLC for degradation over time.
Recommended to discard thawed aliquots after a defined number of days in the refrigerator (set per your internal SOPs) and to avoid more than one freeze–thaw cycle per aliquot.
For definitive stability and storage lifetime, consult the CoA/Spec Sheet and SDS for this specific lot.
Structure and Identity
Gabapentin enacarbil is a prodrug derivative of the GABA analog gabapentin, bearing promoieties that increase lipophilicity and enable carrier‑mediated uptake. It is a small organic molecule intended for research use.
Item-specific (Product Data)
SKU: G176571
Product name: Gabapentin enacarbil
CAS: 478296-72-9
PubChem CID: 9883933
InChIKey: 353821 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Reference identifiers (for context; not item specifications)
A cyclohexane-like backbone bearing an amino substituent and a carboxylate-derived linkage is further masked as mixed carbonate/ester functionalities to form an enacarbil prodrug. The design increases lipophilicity and provides sites for esterase-mediated cleavage to release gabapentin.
Notes
Where exact structural strings (SMILES, full InChI/InChIKey) are required for method development or registration, consult the product’s CoA/Spec Sheet or authoritative databases. All literature values above are provided for general reference only.
Synthetic Utility
As a finished, well-defined small-molecule prodrug, gabapentin enacarbil is not typically employed as a synthetic building block. Nonetheless, understanding its functional groups can inform derivatization or mechanistic studies in research.
Functional group considerations (general)
Ester/carbonate linkages: susceptible to base-catalyzed and enzymatic hydrolysis. Can serve as a model system for prodrug activation or for exploring carbonate stability trends.
Secondary amine (gabapentin core): capable of salt formation and acylation/alkylation under standard conditions; however, access to the free amine may require deprotection/unmasking steps if embedded within the prodrug scaffold.
Potential research transformations
Controlled hydrolysis to obtain the parent gabapentin under mild basic or enzymatic conditions for comparative analytics.
Isotopic labeling (e.g., 13C or 2H) of the promoieties in analogs to trace metabolic fate in mechanistic studies (synthesis of labeled analogs, not modification of the supplied lot, is typically required).
Caveats
Attempting multistep synthesis starting from the prodrug is rarely efficient compared with constructing the gabapentin core followed by prodrug installation. Use this material primarily as a standard or for activation studies rather than as a starting material.
Target Specificity
Not applicable. This product is a small-molecule prodrug standard, not an antibody, protein, or assay-specific ligand with defined immunological target parameters.
Antigen/epitope, clone, isotype, species reactivity: Not applicable to this compound.
For biochemical studies, “specificity” pertains to enzyme and transporter interactions, which are context-dependent and should be determined empirically in your assay system.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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