gabapentin enacarbil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
gabamimetic agents	4177	478296-72-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: gabapentin enacarbil horizant XP13512	Gabapentin enacarbil is a prodrug of gabapentin and, accordingly, its therapeutic effects in restless legs syndrome and postherpetic neuralgia are attributable to gabapentin. In animal models of analgesia, gabapentin prevents allodynia (pain-related behavior in response to a normally innocuous stimulus) and hyperalgesia (exaggerated response to painful stimuli). Molecular weight: 329.39 Formula: C16H27NO6 CLOGP: 3.31 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 101.93 ALOGS: -3.01 ROTB: 9 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

gabapentin enacarbil
horizant
XP13512

Gabapentin enacarbil is a prodrug of gabapentin and, accordingly, its therapeutic effects in restless legs syndrome and postherpetic neuralgia are attributable to gabapentin. In animal models of analgesia, gabapentin prevents allodynia (pain-related behavior in response to a normally innocuous stimulus) and hyperalgesia (exaggerated response to painful stimuli).

Molecular weight: 329.39
Formula: C16H27NO6
CLOGP: 3.31
LIPINSKI: 0
HAC: 7
HDO: 2
TPSA: 101.93
ALOGS: -3.01
ROTB: 9

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
S (Water solubility)	0.50 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
April 6, 2011	FDA	XENOPORT INC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	950.04	34.62	317	1365	246933	63240407
Completed suicide	439.68	34.62	158	1524	145515	63341825
Cardio-respiratory arrest	164.19	34.62	61	1621	59898	63427442
Drug abuse	145.95	34.62	59	1623	72459	63414881
Accidental overdose	111.35	34.62	36	1646	23273	63464067
Myoclonus	42.72	34.62	16	1666	15852	63471488

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	790.59	52.21	262	708	200100	34755861
Completed suicide	324.93	52.21	115	855	98053	34857908
Drug abuse	175.09	52.21	74	896	99022	34856939
Cardio-respiratory arrest	119.95	52.21	48	922	55225	34900736
Accidental overdose	59.60	52.21	22	948	20118	34935843

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	1725.39	33.90	578	1784	420962	79321064
Completed suicide	735.59	33.90	272	2090	245495	79496531
Drug abuse	316.64	33.90	133	2229	162558	79579468
Cardio-respiratory arrest	280.72	33.90	109	2253	108401	79633625
Accidental overdose	189.99	33.90	63	2299	39518	79702508
Myoclonus	79.02	33.90	30	2332	27630	79714396
Intentional product misuse	36.95	33.90	27	2335	95138	79646888

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
CHEBI has role	CHEBI:35623	anticonvulsants
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:38215	calcium channel blockers
CHEBI has role	CHEBI:78298	environmental contaminants
CHEBI has role	CHEBI:50266	Prodrugs
FDA EPC	N0000175753	Anti-epileptic Agent
FDA PE	N0000008486	Decreased Central Nervous System Disorganized Electrical Activity
MeSH PA	D000700	Analgesics
MeSH PA	D014151	Anti-Anxiety Agents
MeSH PA	D000927	Anticonvulsants

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Postherpetic neuralgia	indication	2177002
Restless legs	indication	32914008	DOID:0050425
Partial Epilepsy Treatment Adjunct	off-label use
Suicidal thoughts	contraindication	6471006
Depressive disorder	contraindication	35489007
Kidney disease	contraindication	90708001	DOID:557

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.33	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
300MG	HORIZANT	AZURITY	N022399	Dec. 13, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8686034	Jan. 24, 2025	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
300MG	HORIZANT	AZURITY	N022399	Dec. 13, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8686034	Jan. 24, 2025	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS
300MG	HORIZANT	AZURITY	N022399	Dec. 13, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8114909	April 11, 2026	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS
300MG	HORIZANT	AZURITY	N022399	Dec. 13, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8795725	June 10, 2029	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
300MG	HORIZANT	AZURITY	N022399	Dec. 13, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8795725	June 10, 2029	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8686034	Jan. 24, 2025	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8686034	Jan. 24, 2025	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8114909	April 11, 2026	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8795725	June 10, 2029	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8795725	June 10, 2029	TREATMENT OF MODERATE-TO-SEVERE PRIMARY RESTLESS LEG SYNDROME IN ADULTS

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Voltage-dependent calcium channel subunit alpha-2/delta-1	Ion channel	P54289	CA2D1_HUMAN	MODULATOR				SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Voltage-dependent calcium channel subunit alpha-2/delta-2	Ion channel	Q9NY47	CA2D2_HUMAN	MODULATOR				SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE

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External reference:

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ID	Source
GBN	PDB_CHEM_ID
004415	NDDF
013726	NDDF
108402001	SNOMEDCT_US
1095698	RXNORM
180816	MMSL
27821	MMSL
3446	PUBCHEM_CID
386845007	SNOMEDCT_US
4020833	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Horizant	HUMAN PRESCRIPTION DRUG LABEL	1	53451-0101	TABLET, EXTENDED RELEASE	600 mg	ORAL	NDA	35 sections
Horizant	HUMAN PRESCRIPTION DRUG LABEL	1	53451-0101	TABLET, EXTENDED RELEASE	600 mg	ORAL	NDA	35 sections
Horizant	HUMAN PRESCRIPTION DRUG LABEL	1	53451-0103	TABLET, EXTENDED RELEASE	300 mg	ORAL	NDA	35 sections
Horizant	HUMAN PRESCRIPTION DRUG LABEL	1	53451-0103	TABLET, EXTENDED RELEASE	300 mg	ORAL	NDA	35 sections

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