Details of the Drug

General Information of Drug (ID: DMYT0OG)

Drug Name

Vigabatrin

Synonyms

GVG; Sabril; Sabrilex; Vigabatrina; Vigabatrine; Vigabatrinum; Aventis Brand of Vigabatrin; Gamma Vinyl GABA; Gamma Vinyl gamma Aminobutyric Acid; Hoechst Brand of Vigabatrin; Vigabatrin Aventis Brand; Vigabatrin Hoechst Brand; Vigabatrin Yamanouchi Brand; Vigabatrina [Spanish]; Vigabatrine [French]; Vigabatrinum [Latin]; Yamanouchi Brand of Vigabatrin; M071754; MDL 71754; RMI 71754; V 8261; V8261_SIGMA; CPP-109; Gamma-Vinyl GABA; MDL 71,754; MDL-71754; RMI-71754; RMI-71890; Sabril (TN); Sabrilex (TN); Gamma-Vinyl-GABA; Hexenoic acid, 4-amino; Vigabatrin [USAN:BAN:INN]; Vigabatrin [USAN:INN:BAN]; Gamma-Vinyl-gamma-Aminobutyric Acid; Gamma-Vinyl-gamma-aminobutyric acid; Vigabatrin (JAN/USAN/INN); Acid, gamma-Vinyl-gamma-Aminobutyric; (R,S)-4-Amino-5-hexenoic acid; (inverted question mark)-gamma-Vinyl GABA; 4-Amino-5-hexenoic acid; 4-Aminohexenoic acid; 4-aminohex-5-enoic acid

Indication

Disease Entry	ICD 11	Status	REF
Alcohol dependence	6C40.2	Approved	[1]
Cocaine addiction	6C45.2	Approved	[1]
Complex partial seizure	8A68.0	Approved	[2]
Epilepsy	8A60-8A68	Approved	[2]
Infantile spasm	8A62.0	Approved	[2]
West syndrome	N.A.	Approved	[1]
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Therapeutic Class

Anticonvulsants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

129.16

Logarithm of the Partition Coefficient (xlogp)

-2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2.5 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [5]
Clearance: The apparent oral clearance of drug is 2.4 L/h [3]
Elimination: Approximately 95% of the drug is eliminated in the urine within 72 hours of administration (80% is unchanged parent drug) [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 5.7 hours [3]
Metabolism: The drug is not metabolised [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 442.42001 micromolar/kg/day [6]
Vd: The volume of distribution (Vd) of drug is 1.1 L/kg [3]

Chemical Identifiers

Formula: C6H11NO2
IUPAC Name: 4-aminohex-5-enoic acid
Canonical SMILES: C=CC(CCC(=O)O)N
InChI: InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
InChIKey: PJDFLNIOAUIZSL-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5665
ChEBI ID: CHEBI:63638
CAS Number: 68506-86-5
DrugBank ID: DB01080
TTD ID: D0R3QY
VARIDT ID: DR00270
ACDINA ID: D00727

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA transaminase (ABAT)	TTT2LD9	GABT_HUMAN	Inhibitor	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Proton-coupled amino acid transporter 1 (SLC36A1)	DT48WEM	S36A1_HUMAN	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Vigabatrin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Levomilnacipran	DMV26S8	Moderate	Antagonize the effect of Vigabatrin when combined with Levomilnacipran.	Chronic pain [MG30]	[9]
Sertraline	DM0FB1J	Moderate	Antagonize the effect of Vigabatrin when combined with Sertraline.	Depression [6A70-6A7Z]	[9]
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Vigabatrin when combined with Vilazodone.	Depression [6A70-6A7Z]	[9]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Vigabatrin when combined with Vortioxetine.	Depression [6A70-6A7Z]	[9]
Milnacipran	DMBFE74	Moderate	Antagonize the effect of Vigabatrin when combined with Milnacipran.	Depression [6A70-6A7Z]	[9]
Escitalopram	DMFK9HG	Moderate	Antagonize the effect of Vigabatrin when combined with Escitalopram.	Depression [6A70-6A7Z]	[9]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Vigabatrin when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[9]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Vigabatrin and Esketamine.	Depression [6A70-6A7Z]	[10]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Vigabatrin and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[11]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Vigabatrin and Lasmiditan.	Migraine [8A80]	[12]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Vigabatrin 500 mg tablet	500 mg	Oral Tablet	Oral

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References

1	Vigabatrin FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4821).
3	FDA Approved Drug Products: Sabril (vigabatrin) for oral use
4	BDDCS applied to over 900 drugs
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
8	Rectal absorption of vigabatrin, a substrate of the proton coupled amino acid transporter (PAT1, Slc36a1), in rats. Pharm Res. 2012 Apr;29(4):1134-42.
9	Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
10	Cerner Multum, Inc. "Australian Product Information.".
11	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
12	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.