Gabapentin enacarbil

Gabapentin enacarbil

Systematic (IUPAC) name
(1-{[({(1RS)-1-[isobutyryloxy]ethoxy}carbonyl) amino]methyl}cyclohexyl)acetic acid
Clinical data
Trade names	Horizant, Regnite
Licence data	US FDA:link
Pregnancy category	US: C (Risk not ruled out)
Legal status	US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Excretion	Renal
Identifiers
CAS Number	478296-72-9 Y
PubChem	CID: 9883933
IUPHAR/BPS	7560
ChemSpider	8059607 N
UNII	75OCL1SPBQ N
ChEBI	CHEBI:68840 N
Chemical data
Formula	C16H27NO6
Molecular mass	329.389 g/mol
SMILES CC(C)C(=O)OC(C)OC(=O)NCC1(CCCCC1)CC(=O)O
InChI 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) N Key:TZDUHAJSIBHXDL-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Gabapentin enacarbil (Horizant (in USA), Regnite (in Japan), formerly known as XP-13512) 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.

Gabapentin enacarbil was denied approval by the U.S. Food and Drug Administration (FDA) in February 2010, citing concerns about possible increased cancer risk shown by some animal studies. Similar concerns had been raised about gabapentin itself in the past, but were felt to be outweighed by its clinical utility as an anticonvulsant, whereas the treatment of restless legs syndrome was not seen to justify the same kind of risk.

On April 6, 2011, Xenoport received FDA approval for Horizant (gabapentin enacarbil) for the treatment of moderate-to-severe restless legs syndrome. On June 7, 2012, FDA approved Horizant for the treatment of postherpetic neuralgia in adults.

See also

• Atagabalin
• 4-Methylpregabalin