Gabapentin enacarbil
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MedKoo CAT#: 314219

CAS#: 478296-72-9

Description: 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

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Gabapentin enacarbil
CAS# 478296-72-9

Theoretical Analysis

MedKoo Cat#: 314219
Name: Gabapentin enacarbil
CAS#: 478296-72-9
Chemical Formula: C16H27NO6
Exact Mass: 329.18384
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
25.0mg USD 150.0 2 Weeks
50.0mg USD 250.0 2 Weeks
100.0mg USD 450.0 2 Weeks
200.0mg USD 650.0 2 Weeks
500.0mg USD 850.0 2 Weeks
1.0g USD 1250.0 2 Weeks
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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

Product Data:

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 303.59
Ethanol 100.0 303.59
Water 0.67 2.03

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.

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