vigabatrin ๐Ÿถ Veterinary Use | 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 ยตM/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 1538.82 32.59 560 5520 117314 50481730
Drug withdrawal convulsions 640.84 32.59 115 5965 1238 50597806
Product dose omission issue 283.42 32.59 208 5872 183630 50415414
Magnetic resonance imaging head abnormal 239.71 32.59 53 6027 1724 50597320
Retinogram abnormal 231.31 32.59 35 6045 110 50598934
Death 219.73 32.59 230 5850 325149 50273895
Status epilepticus 218.98 32.59 76 6004 13330 50585714
Drug ineffective 180.99 32.59 337 5743 818996 49780048
Irritability 145.20 32.59 70 6010 28356 50570688
Visual field defect 131.14 32.59 42 6038 5737 50593307
Drug resistance 119.37 32.59 54 6026 18935 50580109
Somnolence 115.61 32.59 116 5964 154869 50444175
Infantile spasms 106.73 32.59 19 6061 193 50598851
Brain operation 95.36 32.59 20 6060 503 50598541
Epilepsy 94.88 32.59 48 6032 21519 50577525
Aggression 84.22 32.59 44 6036 21072 50577972
Tonic convulsion 74.90 32.59 19 6061 1120 50597924
Change in seizure presentation 70.69 32.59 14 6066 262 50598782
Generalised tonic-clonic seizure 67.35 32.59 41 6039 26269 50572775
Focal dyscognitive seizures 66.69 32.59 21 6059 2711 50596333
Partial seizures 65.79 32.59 24 6056 4841 50594203
Respiratory distress 61.80 32.59 41 6039 30448 50568596
Optic atrophy 60.58 32.59 16 6064 1106 50597938
Abnormal behaviour 56.46 32.59 33 6047 19625 50579419
Intellectual disability 55.95 32.59 14 6066 780 50598264
Pneumonia 49.48 32.59 127 5953 378274 50220770
Seizure cluster 49.30 32.59 10 6070 212 50598832
Retinal injury 48.78 32.59 10 6070 224 50598820
Bronchiolitis 48.69 32.59 16 6064 2365 50596679
Infantile spitting up 48.11 32.59 8 6072 52 50598992
Hypotonia 47.52 32.59 22 6058 8112 50590932
Pneumonia aspiration 44.98 32.59 34 6046 30970 50568074
Temporal lobe epilepsy 44.21 32.59 10 6070 360 50598684
Epidural lipomatosis 43.05 32.59 8 6072 105 50598939
Respiratory failure 41.66 32.59 53 6027 91128 50507916
Coma blister 40.53 32.59 8 6072 147 50598897
Pain 40.45 32.59 10 6070 578893 50020151
Multiple-drug resistance 39.85 32.59 15 6065 3299 50595745
Ophthalmological examination abnormal 39.33 32.59 7 6073 71 50598973
Retinal disorder 38.76 32.59 12 6068 1465 50597579
Visual impairment 38.22 32.59 44 6036 68231 50530813
Nausea 37.70 32.59 19 6061 705379 49893665
Anticonvulsant drug level decreased 37.10 32.59 11 6069 1160 50597884
Blindness 36.87 32.59 24 6056 17245 50581799
Rhinovirus infection 35.38 32.59 14 6066 3520 50595524
Respiratory syncytial virus bronchiolitis 34.65 32.59 8 6072 316 50598728
Crying 33.23 32.59 24 6056 20392 50578652
Viral infection 33.07 32.59 28 6052 29958 50569086
Neurotoxicity 32.74 32.59 21 6059 14719 50584325

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 1489.74 39.96 592 5456 92531 29475948
Drug withdrawal convulsions 572.62 39.96 111 5937 1050 29567429
Product dose omission issue 341.18 39.96 223 5825 96160 29472319
Drug ineffective 245.06 39.96 332 5716 362838 29205641
Magnetic resonance imaging head abnormal 204.94 39.96 48 6000 1171 29567308
Status epilepticus 202.75 39.96 78 5970 10716 29557763
Visual field defect 201.42 39.96 61 5987 4055 29564424
Retinogram abnormal 191.27 39.96 31 6017 86 29568393
Brain operation 107.00 39.96 22 6026 285 29568194
Death 105.10 39.96 221 5827 341863 29226616
Infantile spitting up 102.37 39.96 16 6032 32 29568447
Infantile spasms 98.82 39.96 19 6029 170 29568309
Somnolence 94.87 39.96 106 5942 93849 29474630
Visual impairment 86.03 39.96 61 5987 29647 29538832
Epilepsy 83.20 39.96 50 5998 18382 29550097
Sudden unexplained death in epilepsy 71.61 39.96 17 6031 439 29568040
Irritability 69.99 39.96 48 6000 22104 29546375
Ophthalmological examination abnormal 67.99 39.96 11 6037 30 29568449
Partial seizures 65.42 39.96 26 6022 3877 29564602
Optic atrophy 58.03 39.96 16 6032 758 29567721
Anticonvulsant drug level above therapeutic 57.89 39.96 15 6033 559 29567920
Aggression 57.76 39.96 52 5996 35489 29532990
Gaze palsy 53.99 39.96 17 6031 1282 29567197
Multiple-drug resistance 51.81 39.96 22 6026 3878 29564601
Excessive eye blinking 51.46 39.96 13 6035 437 29568042
Respiratory distress 50.25 39.96 46 6002 32060 29536419
Eye movement disorder 49.60 39.96 21 6027 3675 29564804
Postictal paralysis 48.46 39.96 11 6037 232 29568247
Abnormal behaviour 48.11 39.96 39 6009 23088 29545391
Adverse event 47.96 39.96 33 6015 15258 29553221
Tonic convulsion 46.30 39.96 14 6034 922 29567557
Crying 45.15 39.96 22 6026 5329 29563150
Seizure cluster 43.88 39.96 9 6039 115 29568364
Respiratory syncytial virus infection 43.23 39.96 19 6029 3640 29564839
Change in seizure presentation 41.46 39.96 8 6040 73 29568406
Atonic seizures 40.15 39.96 9 6039 179 29568300

FDA Adverse Event Reporting System (Geriatric)

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 1729.13 29.26 692 7988 166200 64323852
Drug withdrawal convulsions 734.52 29.26 141 8539 1987 64488065
Product dose omission issue 459.43 29.26 299 8381 194448 64295604
Retinogram abnormal 404.13 29.26 64 8616 254 64489798
Status epilepticus 367.53 29.26 130 8550 21533 64468519
Death 324.76 29.26 359 8321 482346 64007706
Magnetic resonance imaging head abnormal 212.45 29.26 52 8628 2360 64487692
Visual field defect 205.79 29.26 66 8614 8080 64481972
Drug ineffective 175.94 29.26 362 8318 839885 63650167
Drug resistance 151.40 29.26 80 8600 35022 64455030
Somnolence 150.73 29.26 160 8520 203485 64286567
Infantile spasms 150.30 29.26 27 8653 256 64489796
Brain operation 148.11 29.26 30 8650 561 64489491
Irritability 147.96 29.26 80 8600 36666 64453386
Epilepsy 126.68 29.26 70 8610 33461 64456591
Partial seizures 116.77 29.26 42 8638 7265 64482787
Multiple-drug resistance 102.49 29.26 37 8643 6465 64483587
Respiratory distress 98.03 29.26 70 8610 52261 64437791
Aggression 93.93 29.26 65 8615 46167 64443885
Tonic convulsion 90.11 29.26 25 8655 1856 64488196
Sudden unexplained death in epilepsy 89.53 29.26 20 8660 605 64489447
Generalised tonic-clonic seizure 83.23 29.26 57 8623 39800 64450252
Seizure cluster 76.69 29.26 16 8664 348 64489704
Pneumonia 74.56 29.26 203 8477 559373 63930679
Pneumonia aspiration 71.24 29.26 61 8619 59210 64430842
Bronchiolitis 69.92 29.26 24 8656 3617 64486435
Focal dyscognitive seizures 68.33 29.26 23 8657 3267 64486785
Change in seizure presentation 67.61 29.26 14 8666 293 64489759
Abnormal behaviour 65.30 29.26 46 8634 33576 64456476
Optic atrophy 65.19 29.26 19 8661 1684 64488368
Respiratory disorder 60.11 29.26 45 8635 36066 64453986
Retinal disorder 55.56 29.26 17 8663 1779 64488273
Anticonvulsant drug level above therapeutic 55.41 29.26 15 8665 1015 64489037
Excessive eye blinking 52.42 29.26 15 8665 1245 64488807
Petit mal epilepsy 51.82 29.26 21 8659 5011 64485041
Respiratory failure 51.64 29.26 84 8596 161099 64328953
Electroencephalogram abnormal 51.14 29.26 21 8659 5182 64484870
Rhinovirus infection 51.00 29.26 22 8658 6134 64483918
Postictal paralysis 49.14 29.26 11 8669 336 64489716
Myoclonic epilepsy 48.81 29.26 15 8665 1593 64488459
Respiratory syncytial virus infection 47.49 29.26 22 8658 7246 64482806
Hypotonia 46.73 29.26 25 8655 11187 64478865
Ophthalmological examination abnormal 45.97 29.26 8 8672 62 64489990
Viral infection 45.05 29.26 38 8642 36102 64453950
Crying 44.95 29.26 30 8650 20060 64469992
Nausea 43.64 29.26 26 8654 785774 63704278
Acute kidney injury 43.17 29.26 5 8675 449235 64040817
Temporal lobe epilepsy 43.03 29.26 10 8670 362 64489690
Anticonvulsant drug level decreased 42.82 29.26 14 8666 1816 64488236
Gaze palsy 42.02 29.26 15 8665 2535 64487517
Eye movement disorder 41.86 29.26 20 8660 7059 64482993
Infantile spitting up 40.89 29.26 6 8674 12 64490040
Pain 40.81 29.26 12 8668 553499 63936553
Strabismus 40.69 29.26 14 8666 2123 64487929
Visual impairment 40.69 29.26 50 8630 74027 64416025
Febrile convulsion 39.81 29.26 11 8669 804 64489248
Enterovirus infection 37.57 29.26 12 8668 1445 64488607
Intramyelinic oedema 36.63 29.26 5 8675 4 64490048
Coma blister 36.27 29.26 8 8672 228 64489824
Dysmetria 34.31 29.26 10 8670 886 64489166
Encephalopathy 32.78 29.26 40 8640 58779 64431273
Gingival atrophy 31.95 29.26 6 8674 74 64489978
Lissencephaly 31.66 29.26 4 8676 0 64490052
Posture abnormal 30.95 29.26 13 8667 3393 64486659
Respiratory syncytial virus bronchiolitis 30.80 29.26 8 8672 461 64489591
Apathy 30.62 29.26 19 8661 11213 64478839
Therapeutic product effective for unapproved indication 29.94 29.26 6 8674 106 64489946
Retinal function test abnormal 29.42 29.26 4 8676 3 64490049

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N03AG04 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Fatty acid derivatives
FDA EPC N0000175753 Anti-epileptic Agent
CHEBI has role CHEBI:35623 anticonvulsants
CHEBI has role CHEBI:63674 4-aminobutyrate transaminase inhibitors
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

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
4-aminobutyrate aminotransferase, mitochondrial Enzyme INHIBITOR CHEMBL CHEMBL
Gamma-amino-N-butyrate transaminase Enzyme IC50 4.38 CHEMBL
4-aminobutyrate aminotransferase, mitochondrial Enzyme IC50 4.40 CHEMBL

External reference:

IDSource
4025280 VUID
N0000171807 NUI
D00535 KEGG_DRUG
4025280 VANDF
C0048044 UMLSCUI
CHEBI:63638 CHEBI
CHEMBL89598 ChEMBL_ID
5665 PUBCHEM_CID
DB01080 DRUGBANK_ID
D020888 MESH_DESCRIPTOR_UI
5581 INN_ID
4821 IUPHAR_LIGAND_ID
GR120KRT6K UNII
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 0591-3851 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 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 30 sections
VIGABATRIN HUMAN PRESCRIPTION DRUG LABEL 1 49884-358 POWDER, FOR SOLUTION 50 mg ORAL ANDA 32 sections
Vigabatrin Human Prescription Drug Label 1 59651-366 POWDER, FOR SOLUTION 500 mg ORAL ANDA 32 sections
Vigabatrin Human Prescription Drug Label 1 59651-367 TABLET 500 mg ORAL ANDA 31 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-111 TABLET, FILM COATED 500 mg ORAL NDA 31 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-111 TABLET, FILM COATED 500 mg ORAL NDA 31 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-211 POWDER, FOR SOLUTION 50 mg ORAL NDA 32 sections
SABRIL HUMAN PRESCRIPTION DRUG LABEL 1 67386-211 POWDER, FOR SOLUTION 50 mg ORAL NDA 32 sections
VIGABATRIN Human Prescription Drug Label 1 67877-674 POWDER, FOR SOLUTION 50 mg ORAL ANDA 31 sections
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 68180-521 POWDER, FOR SOLUTION 500 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 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
Vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 69238-1425 FOR SOLUTION 500 mg ORAL ANDA 30 sections
Vigabatrin for oral solution USP, 500 mg HUMAN PRESCRIPTION DRUG LABEL 1 70010-083 FOR SOLUTION 500 mg ORAL ANDA 32 sections
vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 70710-1287 TABLET, FILM COATED 500 mg ORAL ANDA 30 sections
vigabatrin HUMAN PRESCRIPTION DRUG LABEL 1 70771-1654 TABLET, FILM COATED 500 mg ORAL ANDA 30 sections
VIGABATRIN HUMAN PRESCRIPTION DRUG LABEL 1 72158-101 POWDER, FOR SOLUTION 500 mg ORAL ANDA 32 sections
VIGADRONE HUMAN PRESCRIPTION DRUG LABEL 1 73289-0002 POWDER, FOR SOLUTION 50 mg ORAL ANDA 2 sections
VIGADRONE HUMAN PRESCRIPTION DRUG LABEL 1 73289-0003 POWDER, FOR SOLUTION 50 mg ORAL ANDA 2 sections