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

Stem definitionDrug idCAS RN
gabamimetic agents 4177 478296-72-9

Description:

MoleculeDescription

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: OFP

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

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
April 6, 2011 FDA XENOPORT INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 883.69 75.82 173 121 32581 2325210
Completed suicide 393.03 75.82 85 209 20949 2336842
Accidental overdose 166.66 75.82 32 262 3940 2353851
Cardio-respiratory arrest 145.50 75.82 33 261 9113 2348678

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 597.90 239.41 122 63 29019 1717577

Pharmacologic Action:

SourceCodeDescription
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35623 anticonvulsant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.33 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
300MG HORIZANT ARBOR PHARMS LLC N022399 Dec. 13, 2011 RX TABLET, EXTENDED RELEASE ORAL 8048917 Nov. 6, 2022 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG HORIZANT ARBOR PHARMS LLC N022399 April 6, 2011 RX TABLET, EXTENDED RELEASE ORAL 8048917 Nov. 6, 2022 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
300MG HORIZANT ARBOR PHARMS LLC N022399 Dec. 13, 2011 RX TABLET, EXTENDED RELEASE ORAL 8686034 Jan. 24, 2025 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
300MG HORIZANT ARBOR PHARMS LLC 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 ARBOR PHARMS LLC N022399 April 6, 2011 RX TABLET, EXTENDED RELEASE ORAL 8686034 Jan. 24, 2025 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG HORIZANT ARBOR PHARMS LLC 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 ARBOR PHARMS LLC 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 ARBOR PHARMS LLC 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 ARBOR PHARMS LLC N022399 Dec. 13, 2011 RX TABLET, EXTENDED RELEASE ORAL 8795725 June 10, 2029 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
300MG HORIZANT ARBOR PHARMS LLC 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 ARBOR PHARMS LLC N022399 April 6, 2011 RX TABLET, EXTENDED RELEASE ORAL 8795725 June 10, 2029 MANAGEMENT OF POSTHERPETIC NEURALGIA (PHN) IN ADULTS
600MG HORIZANT ARBOR PHARMS LLC 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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Voltage-dependent calcium channel subunit alpha-2/delta-1 Ion channel MODULATOR SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Voltage-dependent calcium channel subunit alpha-2/delta-2 Ion channel MODULATOR SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE

External reference:

IDSource
4030724 VUID
N0000182734 NUI
C2700226 UMLSCUI
D09539 KEGG_DRUG
75OCL1SPBQ UNII
8611 INN_ID
27821 MMSL
1101333 RXNORM
013726 NDDF
4030724 VANDF
703122000 SNOMEDCT_US
C493250 MESH_SUPPLEMENTAL_RECORD_UI
DB08872 DRUGBANK_ID
CHEBI:68840 CHEBI
CHEMBL1628502 ChEMBL_ID
9883933 PUBCHEM_CID
7560 IUPHAR_LIGAND_ID
DB00996 DRUGBANK_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Horizant HUMAN PRESCRIPTION DRUG LABEL 1 53451-0101 TABLET, EXTENDED RELEASE 600 mg ORAL NDA 20 sections
Horizant HUMAN PRESCRIPTION DRUG LABEL 1 53451-0103 TABLET, EXTENDED RELEASE 300 mg ORAL NDA 20 sections