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

Stem definition	Drug id	CAS RN
gabamimetic agents	2819	68506-86-5

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2	g	O

ADMET properties:

Property	Value	Reference
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 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Aug. 21, 2009	FDA	LUNDBECK LLC

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
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 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
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 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
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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
4-aminobutyrate aminotransferase, mitochondrial	Enzyme	P80404	GABT_HUMAN	INHIBITOR			CHEMBL	CHEMBL
Gamma-amino-N-butyrate transaminase	Enzyme		GABT_RAT		IC50	4.38	CHEMBL
4-aminobutyrate aminotransferase, mitochondrial	Enzyme		GABT_MOUSE		IC50	4.40	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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