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MedKoo Cat#: 314219 | Name: Gabapentin enacarbil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gabapentin enacarbil is a prodrug for the anticonvulsant and analgesic drug gabapentin. It was designed for increased oral bioavailability over gabapentin, and human trials showed it to produce extended release of gabapentin with almost twice the overall bioavailability, especially when taken with a fatty meal. Gabapentin enacarbil has passed human clinical trials for the treatment of restless legs syndrome, and initial results have shown it to be well tolerated and reasonably effective. (Source: http://en.wikipedia.org/wiki/Gabapentin_enacarbil).

Chemical Structure

Gabapentin enacarbil
Gabapentin enacarbil
CAS#478296-72-9 (enacarbil)

Theoretical Analysis

MedKoo Cat#: 314219

Name: Gabapentin enacarbil

CAS#: 478296-72-9 (enacarbil)

Chemical Formula: C16H27NO6

Exact Mass: 329.1838

Molecular Weight: 329.39

Elemental Analysis: C, 58.34; H, 8.26; N, 4.25; O, 29.14

Price and Availability

Size Price Availability Quantity
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,950.00 2 Weeks
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Related CAS #
60142-95-2 (HCl) 60142-96-3 (free base) 478296-72-9 (enacarbil)
Synonym
Horizant; Regnite
IUPAC/Chemical Name
(1-{[({(1RS)-1-[isobutyryloxy]ethoxy}carbonyl) amino]methyl}cyclohexyl)acetic acid
InChi Key
TZDUHAJSIBHXDL-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
SMILES Code
O=C(O)CC1(CNC(OC(OC(C(C)C)=O)C)=O)CCCCC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin.
In vitro activity:
It’s found that 10 mM gabapentin reduces the growth of HCT116 cells, which have an active branched-chain amino acid transferase but express very low levels of BCAT1, and presumably rely on the mitochondrial BCAT2 enzyme. Gabapentin did not affect transamination of BCAA to branched-chain keto acids (BCKA) in HCT116 cells, nor the reverse formation of BCAA from BCKA, indicating that the branched-chain amino acid transaminase is not inhibited. Moreover, the growth-inhibitory effect of gabapentin could not be rescued by supplementation with BCKA, and this was not due to the lack of uptake of BCKA, indicating that other effects of gabapentin are important. An untargeted LC-MS analysis of gabapentin-treated cells revealed a marked depletion of branched-chain carnitines. These results demonstrate that gabapentin at high concentrations can inhibit cell proliferation without affecting BCAT1 and may affect mitochondrial BCKA catabolism. Reference: Biochemistry. 2018 Dec 11;57(49):6762-6766. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30427175/
In vivo activity:
The antipruritic activity of gabapentin, an anticonvulsant, was studied in a mouse model of allergic itch. In mice sensitized by an extract of the salivary glands of the mosquito (ESGM), an intradermal injection of ESGM elicited scratching and increased peripheral nerve firing. Oral or intradermal administration of gabapentin at the ESGM injection site inhibited ESGM-induced scratching and peripheral nerve firing. However, gabapentin did not affect histamine-induced scratching. The distributions of immunoreactivity to the voltage-dependent calcium channel α2δ-1 subunit, a site of gabapentin action, and the histamine H1 receptor differed in the mouse dorsal root ganglia. The α2δ-1 subunit was mainly found in neurons that were 15-20 µm in diameter, whereas the H1 receptor was mainly in 20-30 µm neurons. In addition, α2δ-1 subunit immunoreactivity co-localized with that of transient receptor potential vanilloid 1 (TRPV1). These results suggest that gabapentin regulates allergic itch by acting on the calcium channel α2δ-1 subunit in peripheral TRPV1-positive neurons. Reference: Eur J Pharmacol. 2018 Aug 15;833:44-49. https://linkinghub.elsevier.com/retrieve/pii/S0014-2999(18)30308-X
Solvent mg/mL mM
Solubility
DMSO 100.0 303.59
Ethanol 100.0 303.59
Water 0.7 2.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 329.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Grankvist N, Lagerborg KA, Jain M, Nilsson R. Gabapentin Can Suppress Cell Proliferation Independent of the Cytosolic Branched-Chain Amino Acid Transferase 1 (BCAT1). Biochemistry. 2018 Dec 11;57(49):6762-6766. doi: 10.1021/acs.biochem.8b01031. Epub 2018 Nov 26. PMID: 30427175; PMCID: PMC6528808. 2. Akiyama T, Andoh T, Ohtsuka E, Nojima H, Ouchi H, Takahata H, Kuraishi Y. Peripheral gabapentin regulates mosquito allergy-induced itch in mice. Eur J Pharmacol. 2018 Aug 15;833:44-49. doi: 10.1016/j.ejphar.2018.05.037. Epub 2018 May 26. PMID: 29842875. 3. Ceretta APC, de Freitas CM, Schaffer LF, Reinheimer JB, Dotto MM, de Moraes Reis E, Scussel R, Machado-de-Ávila RA, Fachinetto R. Gabapentin reduces haloperidol-induced vacuous chewing movements in mice. Pharmacol Biochem Behav. 2018 Mar;166:21-26. doi: 10.1016/j.pbb.2018.01.003. Epub 2018 Jan 31. PMID: 29374574.
In vitro protocol:
1. Grankvist N, Lagerborg KA, Jain M, Nilsson R. Gabapentin Can Suppress Cell Proliferation Independent of the Cytosolic Branched-Chain Amino Acid Transferase 1 (BCAT1). Biochemistry. 2018 Dec 11;57(49):6762-6766. doi: 10.1021/acs.biochem.8b01031. Epub 2018 Nov 26. PMID: 30427175; PMCID: PMC6528808.
In vivo protocol:
1. Akiyama T, Andoh T, Ohtsuka E, Nojima H, Ouchi H, Takahata H, Kuraishi Y. Peripheral gabapentin regulates mosquito allergy-induced itch in mice. Eur J Pharmacol. 2018 Aug 15;833:44-49. doi: 10.1016/j.ejphar.2018.05.037. Epub 2018 May 26. PMID: 29842875. 2. Ceretta APC, de Freitas CM, Schaffer LF, Reinheimer JB, Dotto MM, de Moraes Reis E, Scussel R, Machado-de-Ávila RA, Fachinetto R. Gabapentin reduces haloperidol-induced vacuous chewing movements in mice. Pharmacol Biochem Behav. 2018 Mar;166:21-26. doi: 10.1016/j.pbb.2018.01.003. Epub 2018 Jan 31. PMID: 29374574.
 1: Ray LA, Grodin EN, Baskerville WA, Donato S, Cruz A, Montoya AK. Identifying responders to gabapentin for the treatment of alcohol use disorder: an exploratory machine learning approach. Alcohol Alcohol. 2025 Mar 25;60(3):agaf010. doi: 10.1093/alcalc/agaf010. PMID: 40138385; PMCID: PMC11938997. 2: Richards KC, Fry LM, Lozano AJ, Ji W, Morrison JD, Britt KC, Bliwise DL, Gooneratne NS, Hanlon AL. Treatment of Restless Legs Syndrome Improves Agitation and Sleep in Persons with Dementia: A Randomized Trial. J Am Med Dir Assoc. 2025 Mar 31;26(5):105485. doi: 10.1016/j.jamda.2025.105485. Epub ahead of print. PMID: 39909068. 3: Parker N, Koch E, Shadrin AA, Fuhrer J, Hindley GFL, Stinson S, Jaholkowski P, Tesfaye M, Dale AM, Wingo TS, Wingo AP, Frei O, O'Connell KS, Smeland OB, Andreassen OA. Leveraging the Genetics of Psychiatric Disorders to Prioritize Potential Drug Targets and Compounds. medRxiv [Preprint]. 2024 Sep 24:2024.09.24.24314069. doi: 10.1101/2024.09.24.24314069. PMID: 39399035; PMCID: PMC11469398. 4: Winkelman JW, Berkowski JA, DelRosso LM, Koo BB, Scharf MT, Sharon D, Zak RS, Kazmi U, Falck-Ytter Y, Shelgikar AV, Trotti LM, Walters AS. Treatment of restless legs syndrome and periodic limb movement disorder: an American Academy of Sleep Medicine clinical practice guideline. J Clin Sleep Med. 2025 Jan 1;21(1):137-152. doi: 10.5664/jcsm.11390. PMID: 39324694; PMCID: PMC11701286. 5: Bi W, Yang M, Mao R. Unraveling Shared Diagnostic Biomarkers of Fibromyalgia in Ankylosing Spondylitis: Evidence from Comprehensive Bioinformatic Analysis and Experimental Validation. J Inflamm Res. 2024 Sep 16;17:6395-6413. doi: 10.2147/JIR.S474984. PMID: 39310900; PMCID: PMC11415292. 6: Garcia CC, Richards DK, Tuchman FR, Hallgren KA, Kranzler HR, Aubin HJ, O'Malley SS, Mann K, Aldridge A, Hoffman M, Anton RF, Witkiewitz K. Reductions in World Health Organization risk drinking level are associated with improvements in sleep problems among individuals with alcohol use disorder. Alcohol Alcohol. 2024 Mar 16;59(3):agae022. doi: 10.1093/alcalc/agae022. PMID: 38606931; PMCID: PMC11010310. 7: Richards DK, Tuchman FR, Hallgren KA, Kranzler HR, Aubin HJ, O'Malley SS, Mann K, Aldridge A, Anton RF, Witkiewitz K. Reductions in World Health Organization Risk Drinking Level Are Associated With Reductions in Alcohol Use Disorder Diagnosis and Criteria: Evidence From an Alcohol Pharmacotherapy Trial. J Addict Med. 2024 Jul-Aug 01;18(4):418-424. doi: 10.1097/ADM.0000000000001303. Epub 2024 Apr 11. PMID: 38606854; PMCID: PMC11290995. 8: Pellitteri G, Versace S, Merlino G, Nilo A, Gigli GL, Valente M. A comprehensive update on the ADMET considerations for α2δ calcium channel ligand medications for treating restless legs syndrome. Expert Opin Drug Metab Toxicol. 2024 Mar;20(3):133-142. doi: 10.1080/17425255.2024.2329738. Epub 2024 Mar 15. PMID: 38482850. 9: Khan M. Restless Legs Syndrome and Other Common Sleep-Related Movement Disorders. Continuum (Minneap Minn). 2023 Aug 1;29(4):1130-1148. doi: 10.1212/CON.0000000000001269. PMID: 37590826. 10: Tang J, Zhang Y, Liu C, Zeng A, Song L. Therapeutic Strategies for Postherpetic Neuralgia: Mechanisms, Treatments, and Perspectives. Curr Pain Headache Rep. 2023 Sep;27(9):307-319. doi: 10.1007/s11916-023-01146-x. Epub 2023 Jul 26. PMID: 37493871. 11: Zhang H, Feng T. Network-Based Data Analysis Reveals Ion Channel-Related Gene Features in COVID-19: A Bioinformatic Approach. Biochem Genet. 2023 Apr;61(2):471-505. doi: 10.1007/s10528-022-10280-x. Epub 2022 Sep 14. PMID: 36104591; PMCID: PMC9473477. 12: Winkelman JW. Treating Severe Refractory and Augmented Restless Legs Syndrome. Chest. 2022 Sep;162(3):693-700. doi: 10.1016/j.chest.2022.05.014. Epub 2022 May 21. PMID: 35609673. 13: Costales B, Vouri SM, Brown JD, Setlow B, Goodin AJ. Treatment initiation and utilization patterns of pharmacotherapies for early-onset idiopathic restless legs syndrome. Sleep Med. 2022 Aug;96:70-78. doi: 10.1016/j.sleep.2022.05.003. Epub 2022 May 13. PMID: 35605349; PMCID: PMC9385069. 14: Ayad SS, Makarova N, Niazi AK, Khoshknabi DS, Stang T, Raza S, Kim DD. Effects of Gabapentin Enacarbil on Postoperative Pain After Hip and Knee Arthroplasty: A Placebo-controlled Randomized Trial. Clin J Pain. 2022 Feb 7;38(4):250-256. doi: 10.1097/AJP.0000000000001024. PMID: 35132024. 15: Zhou X, Du J, Liang Y, Dai C, Zhao L, Liu X, Tan C, Mo L, Chen L. The Efficacy and Safety of Pharmacological Treatments for Restless Legs Syndrome: Systemic Review and Network Meta-Analysis. Front Neurosci. 2021 Oct 26;15:751643. doi: 10.3389/fnins.2021.751643. PMID: 34764852; PMCID: PMC8576256. 16: Lal R, Ellenbogen A, Gidal B. Interindividual Variability in the Bioavailability of Gabapentin Enacarbil Extended Release in Healthy Adults: An Analysis of Data From 6 Phase I Studies. Ther Drug Monit. 2022 Jun 1;44(3):448-454. doi: 10.1097/FTD.0000000000000935. Epub 2021 Nov 1. PMID: 34726199; PMCID: PMC9083487. 17: Inoue Y, Hirata K, Hoshino Y, Yamaguchi Y. Difference in background factors between responders to gabapentin enacarbil treatment and responders to placebo: pooled analyses of two randomized, double-blind, placebo-controlled studies in Japanese patients with restless legs syndrome. Sleep Med. 2021 Sep;85:138-146. doi: 10.1016/j.sleep.2021.07.004. Epub 2021 Jul 7. PMID: 34329897. 18: Richards K, Britt KC, Cuellar N, Wang Y, Morrison J. Clinical Decision- Making: Restless Legs Syndrome and Dementia in Older Adults. Nurs Clin North Am. 2021 Jun;56(2):265-274. doi: 10.1016/j.cnur.2021.02.005. PMID: 34023120. 19: Gao X, Ba DM, Bagai K, Liu G, Ma C, Walters AS. Treating Restless Legs Syndrome Was Associated With Low Risk of Cardiovascular Disease: A Cohort Study With 3.4 Years of Follow-Up. J Am Heart Assoc. 2021 Feb 16;10(4):e018674. doi: 10.1161/JAHA.120.018674. Epub 2021 Feb 8. PMID: 33550813; PMCID: PMC7955352. 20: Laska EM, Siegel CE, Lin Z, Bogenschutz M, Marmar CR. Gabapentin Enacarbil Extended-Release Versus Placebo: A Likely Responder Reanalysis of a Randomized Clinical Trial. Alcohol Clin Exp Res. 2020 Sep;44(9):1875-1884. doi: 10.1111/acer.14414. Epub 2020 Jul 31. PMID: 33460198; PMCID: PMC7540534.