vigabatrin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
gabamimetic agents 2819 68506-86-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • vigabatrin
  • (+/-)-4-Amino-5-hexenoic acid
  • sabril
  • vigabatrin hydrochloride
  • vigabatrin HCl
The precise mechanism of vigabatrin's anti-seizure effect is unknown, but it is believed to be the result of its action as an irreversible inhibitor of gamma-aminobutyric acid transaminase (GABA-T), the enzyme responsible for the metabolism of the inhibitory neurotransmitter GABA. This action results in increased levels of GABA in the central nervous system.
  • Molecular weight: 129.16
  • Formula: C6H11NO2
  • CLOGP: -2.22
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 63.32
  • ALOGS: -0.13
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
2 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 60 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 442.42 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Aug. 21, 2009 FDA LUNDBECK LLC

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
Seizure 1559.26 32.46 576 5209 122478 46557799
Drug withdrawal convulsions 605.69 32.46 110 5675 1231 46679046
Infantile spasms 391.43 32.46 60 5725 203 46680074
Product dose omission issue 273.29 32.46 199 5586 168321 46511956
Retinogram abnormal 209.21 32.46 32 5753 106 46680171
Drug ineffective 195.60 32.46 319 5466 677519 46002758
Death 192.61 32.46 221 5564 335327 46344950
Epilepsy 184.40 32.46 79 5706 23659 46656618
Status epilepticus 176.35 32.46 66 5719 13913 46666364
Irritability 138.98 32.46 69 5716 28877 46651400
Visual field defect 123.74 32.46 41 5744 6042 46674235
Somnolence 109.88 32.46 115 5670 156406 46523871
Brain operation 98.10 32.46 20 5765 422 46679855
Aggression 77.14 32.46 43 5742 22701 46657576
Change in seizure presentation 70.46 32.46 14 5771 258 46680019
Tonic convulsion 69.97 32.46 18 5767 1088 46679189
Focal dyscognitive seizures 69.46 32.46 22 5763 2806 46677471
Partial seizures 64.38 32.46 24 5761 4986 46675291
Drug resistance 62.08 32.46 34 5751 17334 46662943
Generalised tonic-clonic seizure 57.63 32.46 38 5747 27084 46653193
Respiratory distress 56.63 32.46 40 5745 31876 46648401
Optic atrophy 55.64 32.46 15 5770 1087 46679190
Abnormal behaviour 53.42 32.46 33 5752 21025 46659252
Seizure cluster 51.25 32.46 10 5775 167 46680110
Infantile spitting up 49.16 32.46 8 5777 43 46680234
Retinal injury 49.04 32.46 10 5775 211 46680066
Intellectual disability 47.57 32.46 12 5773 670 46679607
Temporal lobe epilepsy 43.56 32.46 10 5775 373 46679904
Pneumonia 43.44 32.46 123 5662 376197 46304080
Epidural lipomatosis 42.80 32.46 8 5777 105 46680172
Pneumonia aspiration 41.33 32.46 33 5752 31572 46648705
Coma blister 40.28 32.46 8 5777 147 46680130
Ophthalmological examination abnormal 38.85 32.46 7 5778 74 46680203
Nausea 38.06 32.46 19 5766 687435 45992842
Hypotonia 37.62 32.46 19 5766 8210 46672067
Bronchiolitis 37.05 32.46 13 5772 2272 46678005
Blindness 36.20 32.46 24 5761 17245 46663032
Respiratory failure 35.75 32.46 51 5734 94765 46585512
Visual impairment 34.65 32.46 42 5743 66647 46613630
Rhinovirus infection 34.58 32.46 14 5771 3622 46676655
Respiratory syncytial virus bronchiolitis 34.38 32.46 8 5777 317 46679960
Pain 33.38 32.46 9 5776 476939 46203338
Therapeutic product effective for unapproved indication 32.60 32.46 6 5779 72 46680205

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
Seizure 1539.48 40.74 597 4912 97878 29849091
Drug withdrawal convulsions 547.18 40.74 105 5404 1054 29945915
Infantile spasms 503.24 40.74 80 5429 219 29946750
Product dose omission issue 340.03 40.74 210 5299 91421 29855548
Drug ineffective 226.74 40.74 293 5216 340094 29606875
Visual field defect 203.32 40.74 61 5448 4375 29942594
Retinogram abnormal 175.38 40.74 28 5481 79 29946890
Status epilepticus 162.51 40.74 65 5444 11007 29935962
Brain operation 109.99 40.74 22 5487 276 29946693
Death 98.08 40.74 207 5302 357076 29589893
Infantile spitting up 96.91 40.74 15 5494 32 29946937
Somnolence 91.03 40.74 100 5409 96663 29850306
Visual impairment 83.45 40.74 58 5451 30380 29916589
Epilepsy 78.78 40.74 48 5461 20121 29926848
Ophthalmological examination abnormal 68.38 40.74 11 5498 33 29946936
Sudden unexplained death in epilepsy 68.34 40.74 16 5493 434 29946535
Irritability 63.33 40.74 44 5465 23006 29923963
Aggression 60.85 40.74 52 5457 36855 29910114
Optic atrophy 59.68 40.74 16 5493 760 29946209
Postictal paralysis 55.36 40.74 11 5498 133 29946836
Respiratory distress 53.42 40.74 46 5463 32926 29914043
Partial seizures 51.37 40.74 21 5488 3746 29943223
Respiratory syncytial virus infection 46.69 40.74 19 5490 3349 29943620
Crying 46.39 40.74 22 5487 5587 29941382
Abnormal behaviour 46.13 40.74 38 5471 25585 29921384
Seizure cluster 44.62 40.74 9 5500 118 29946851

Pharmacologic Action:

SourceCodeDescription
ATC N03AG04 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Fatty acid derivatives
FDA EPC N0000175753 Anti-epileptic Agent
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018682 GABA Agents
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:63674 4-aminobutyrate transaminase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
West syndrome indication 28055006
Epilepsy characterized by intractable complex partial seizures indication 442481002
Suicidal thoughts contraindication 6471006
Weight gain finding contraindication 8943002
Visual field defect contraindication 12184005
Reduced visual acuity contraindication 13164000
Mood swings contraindication 18963009
Kidney disease contraindication 90708001 DOID:557
Edema contraindication 267038008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Peripheral nerve disease contraindication 302226006
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.94 acidic
pKa2 10.16 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
500MG VIGABATRIN DR REDDYS A211539 Jan. 29, 2021 RX TABLET ORAL July 31, 2021 COMPETITIVE GENERIC THERAPY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
4-aminobutyrate aminotransferase, mitochondrial Enzyme INHIBITOR CHEMBL CHEMBL
Gamma-amino-N-butyrate transaminase Unclassified IC50 4.38 CHEMBL

External reference:

IDSource
4025280 VUID
N0000171807 NUI
D00535 KEGG_DRUG
4025280 VANDF
C0592085 UMLSCUI
CHEBI:63638 CHEBI
CHEMBL89598 ChEMBL_ID
D020888 MESH_DESCRIPTOR_UI
5581 INN_ID
GR120KRT6K UNII
5665 PUBCHEM_CID
4821 IUPHAR_LIGAND_ID
DB01080 DRUGBANK_ID
14851 RXNORM
15507 MMSL
36115 MMSL
52922 MMSL
d04669 MMSL
003774 NDDF
310283001 SNOMEDCT_US
322976008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Vigabatrin for oral solution USP, 500 mg HUMAN PRESCRIPTION DRUG LABEL 1 0054-0702 FOR SOLUTION 50 mg ORAL ANDA 33 sections
VIGADRONE HUMAN PRESCRIPTION DRUG LABEL 1 0245-0556 POWDER, FOR SOLUTION 50 mg ORAL ANDA 35 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 0591-3851 TABLET, FILM COATED 500 mg ORAL ANDA 29 sections
vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 0591-3955 POWDER, FOR SOLUTION 50 mg ORAL ANDA 30 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 16729-521 POWDER, FOR SOLUTION 500 mg ORAL ANDA 33 sections
vigabatrin for oral solution HUMAN PRESCRIPTION DRUG LABEL 1 31722-009 POWDER, FOR SOLUTION 50 mg ORAL ANDA 36 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 43598-651 TABLET, FILM COATED 500 mg ORAL ANDA 32 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 43598-697 POWDER, FOR SOLUTION 50 mg ORAL ANDA 31 sections
VIGABATRIN HUMAN PRESCRIPTION DRUG LABEL 1 49884-358 POWDER, FOR SOLUTION 50 mg ORAL ANDA 32 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-111 TABLET, FILM COATED 500 mg ORAL NDA 32 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-211 POWDER, FOR SOLUTION 50 mg ORAL NDA 33 sections
VIGABATRIN Human Prescription Drug Label 1 67877-674 POWDER, FOR SOLUTION 50 mg ORAL ANDA 31 sections
VIGABATRIN HUMAN PRESCRIPTION DRUG LABEL 1 69097-964 POWDER, FOR SOLUTION 500 mg ORAL ANDA 32 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 69238-1425 FOR SOLUTION 500 mg ORAL ANDA 30 sections