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:

None

Approvals:

Date	Agency	Company	Orphan
April 6, 2011	FDA	XENOPORT INC

FDA Adverse Event Reporting System (Female)

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	740.88	35.39	256	1139	212243	50391486
Completed suicide	363.00	35.39	135	1260	131754	50471975
Cardio-respiratory arrest	131.71	35.39	51	1344	53841	50549888
Accidental overdose	116.29	35.39	36	1359	19497	50584232
Drug abuse	67.87	35.39	33	1362	59813	50543916
Myoclonus	39.88	35.39	15	1380	14455	50589274

FDA Adverse Event Reporting System (Male)

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	596.88	64.90	187	397	173474	29400469
Completed suicide	263.67	64.90	88	496	90158	29483785
Cardio-respiratory arrest	113.69	64.90	41	543	50560	29523383
Drug abuse	82.42	64.90	37	547	79846	29494097
Accidental overdose	70.02	64.90	22	562	17571	29556372

FDA Adverse Event Reporting System (Geriatric)

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	1306.30	39.78	443	1325	363070	64133894
Completed suicide	597.76	39.78	223	1545	224191	64272773
Cardio-respiratory arrest	237.72	39.78	92	1676	98301	64398663
Accidental overdose	205.31	39.78	63	1705	33494	64463470
Drug abuse	142.07	39.78	70	1698	132304	64364660
Myoclonus	80.39	39.78	29	1739	25089	64471875

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
FDA PE	N0000008486	Decreased Central Nervous System Disorganized Electrical Activity
MeSH PA	D000700	Analgesics
MeSH PA	D014151	Anti-Anxiety Agents
MeSH PA	D000927	Anticonvulsants
MeSH PA	D018692	Antimanic Agents
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D018691	Excitatory Amino Acid Antagonists
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D011619	Psychotropic Drugs
MeSH PA	D018689	Sensory System Agents
MeSH PA	D014149	Tranquilizing Agents
FDA EPC	N0000175753	Anti-epileptic Agent
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

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

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

🐶 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)

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	8048917	Nov. 6, 2022	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG	HORIZANT	AZURITY	N022399	April 6, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8048917	Nov. 6, 2022	MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
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
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
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
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
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	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

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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

External reference:

ID	Source
4030724	VUID
N0000182734	NUI
D09539	KEGG_DRUG
4020833	VANDF
4030724	VANDF
C2700226	UMLSCUI
CHEBI:68840	CHEBI
CHEBI:42797	CHEBI
GBN	PDB_CHEM_ID
CHEMBL1628502	ChEMBL_ID
DB08872	DRUGBANK_ID
C493250	MESH_SUPPLEMENTAL_RECORD_UI
7560	IUPHAR_LIGAND_ID
8611	INN_ID
75OCL1SPBQ	UNII
9883933	PUBCHEM_CID
3446	PUBCHEM_CID
DB00996	DRUGBANK_ID
1095698	RXNORM
180816	MMSL
27821	MMSL
4770	MMSL
60712	MMSL
d03182	MMSL
004415	NDDF
013726	NDDF
108402001	SNOMEDCT_US
386845007	SNOMEDCT_US
703122000	SNOMEDCT_US
C0060926	UMLSCUI
D000077206	MESH_DESCRIPTOR_UI
5094	INN_ID

Pharmaceutical products:

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	53451-0103	TABLET, EXTENDED RELEASE	300 mg	ORAL	NDA	35 sections