Gabapentin enacarbil

Modify Date: 2024-01-04 17:41:03

Gabapentin enacarbil structure	Common Name	Gabapentin enacarbil
	CAS Number	478296-72-9	Molecular Weight	329.389
	Density	1.1±0.1 g/cm3	Boiling Point	482.0±20.0 °C at 760 mmHg
	Molecular Formula	C₁₆H₂₇NO₆	Melting Point	65ºC
	MSDS	N/A	Flash Point	245.3±21.8 °C

Use of Gabapentin enacarbil

Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin.IC50 Value: Target: Calcium ChannelGabapentin enacarbil is an actively transported prodrug of gabapentin that provides sustained dose-proportional exposure to gabapentin and predictable bioavailability.in vitro: The prodrug (XP-13512) demonstrated active apical to basolateral transport across Caco-2 cell monolayers and pH-dependent passive permeability across artificial membranes. XP13512 inhibited uptake of (14)C-lactate by human embryonic kidney cells expressing monocarboxylate transporter type-1, and direct uptake of prodrug by these cells was confirmed using liquid chromatography-tandem mass spectrometry. XP13512 inhibited uptake of (3)H-biotin into Chinese hamster ovary cells overexpressing human sodium-dependent multivitamin transporter (SMVT) [1].in vivo: In 4 studies of healthy volunteers (136 subjects total), the pharmacokinetics of XP13512 immediate- and extended-release formulations were compared with those of oral gabapentin. XP13512 immediate-release (up to 2800 mg single dose and 2100 mg twice daily) was well absorbed (>68%, based on urinary recovery of gabapentin), converted rapidly to gabapentin, and provided dose-proportional exposure, whereas absorption of oral gabapentin declined with increasing doses to <27% at 1200 mg. Compared with 600 mg gabapentin, an equimolar XP13512 extended-release dose provided extended gabapentin exposure (time to maximum concentration, 8.4 vs 2.7 hours) and superior bioavailability (74.5% vs 36.6%) [2].Toxicity: Gabapentin's most common side effects in adult patients include dizziness, fatigue, weight gain, drowsiness, and peripheral edema (swelling of extremities).

Name	gabapentin enacarbil
Synonym	More Synonyms

Description	Gabapentin enacarbil (XP-13512) is a prodrug for the anticonvulsant and analgesic drug gabapentin.IC50 Value: Target: Calcium ChannelGabapentin enacarbil is an actively transported prodrug of gabapentin that provides sustained dose-proportional exposure to gabapentin and predictable bioavailability.in vitro: The prodrug (XP-13512) demonstrated active apical to basolateral transport across Caco-2 cell monolayers and pH-dependent passive permeability across artificial membranes. XP13512 inhibited uptake of (14)C-lactate by human embryonic kidney cells expressing monocarboxylate transporter type-1, and direct uptake of prodrug by these cells was confirmed using liquid chromatography-tandem mass spectrometry. XP13512 inhibited uptake of (3)H-biotin into Chinese hamster ovary cells overexpressing human sodium-dependent multivitamin transporter (SMVT) [1].in vivo: In 4 studies of healthy volunteers (136 subjects total), the pharmacokinetics of XP13512 immediate- and extended-release formulations were compared with those of oral gabapentin. XP13512 immediate-release (up to 2800 mg single dose and 2100 mg twice daily) was well absorbed (>68%, based on urinary recovery of gabapentin), converted rapidly to gabapentin, and provided dose-proportional exposure, whereas absorption of oral gabapentin declined with increasing doses to <27% at 1200 mg. Compared with 600 mg gabapentin, an equimolar XP13512 extended-release dose provided extended gabapentin exposure (time to maximum concentration, 8.4 vs 2.7 hours) and superior bioavailability (74.5% vs 36.6%) [2].Toxicity: Gabapentin's most common side effects in adult patients include dizziness, fatigue, weight gain, drowsiness, and peripheral edema (swelling of extremities).
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Research Areas >> Neurological Disease
References	[1]. Cundy KC, et al. XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters. J Pha [2]. Cundy KC, et al. Clinical pharmacokinetics of XP13512, a novel transported prodrug of gabapentin. J Clin Pharmacol. 2008 Dec;48(12):1378-88.

Description

Related Catalog

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Neurological Disease

References

[1]. Cundy KC, et al. XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters. J Pha

[2]. Cundy KC, et al. Clinical pharmacokinetics of XP13512, a novel transported prodrug of gabapentin. J Clin Pharmacol. 2008 Dec;48(12):1378-88.

Density	1.1±0.1 g/cm3
Boiling Point	482.0±20.0 °C at 760 mmHg
Melting Point	65ºC
Molecular Formula	C₁₆H₂₇NO₆
Molecular Weight	329.389
Flash Point	245.3±21.8 °C
Exact Mass	329.183838
PSA	101.93000
LogP	3.07
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.481
Storage condition	2-8℃

Precursor 9
CAS#:860035-10-5 Propanoic acid,... CAS#:60142-96-3 Gabapentin CAS#:1164116-60-2 1-[(chlorocarbo... CAS#:194995-47-6 1-(((4-NITROPHE...
CAS#:850479-14-0 1-{[(α-chloroet... CAS#:79-31-2 Isobutyric acid CAS#:1201785-64-9 1-(aminomethyl)... CAS#:1201785-62-7 O-1-(isobutyryl...
CAS#:649748-02-7 trimethylsilyl ...
DownStream 0