CAS 478296-72-9|Gabapentin enacarbil

Introduction：Basic information about CAS 478296-72-9|Gabapentin enacarbil, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Gabapentin enacarbil BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

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	/	Flash Point	245.3±21.8 °C

Names

Name	gabapentin enacarbil
Synonym	More Synonyms

Gabapentin enacarbil BiologicalActivity

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 ChannelResearch 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

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 ChannelResearch 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.

Chemical & Physical Properties

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
InChIKey	TZDUHAJSIBHXDL-UHFFFAOYSA-N
SMILES	CC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C
Storage condition	2-8℃

Synonyms

{[(1-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexaneacetic acid

{1-[({[1-(Isobutyryloxy)ethoxy]carbonyl}amino)methyl]cyclohexyl}acetic acid

Solzira

Cyclohexaneacetic acid, 1-[[[[1-(2-methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]-

UNII-75OCL1SPBQ

UNII:75OCL1SPBQ

Horizant

2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid

ASP-8825

Gabapentin enacarbil

Xenoport

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