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    Vigabatrin molecular structure

    Vigabatrin Stats & Data

    PubChem
    MW129.16
    FormulaC6H11NO2
    LogP-2.2
    IUPAC4-aminohex-5-enoic acid
    InChIKeyPJDFLNIOAUIZSL-UHFFFAOYSA-N
    Psychoactive Class Depressant

    Pharmacology

    DrugBank
    State Solid

    Description

    Vigabatrin is an analog of gamma-aminobutyric acid (GABA), the main inhibitory neurotransmitter in the central nervous system, used in the treatment of refractory seizures and infantile spasms. It irreversibly inhibits the enzyme responsible for GABA metabolism, thereby increasing levels of circulating GABA. Although administered as a racemic mixture, only the S(+) enantiomer is pharmacologically active. It was first introduced as an antiepileptic agent in the United Kingdom in 1989 and was used extensively until 1997, when an association with vision loss became apparent. Its use is now generally reserved for patients who have failed alternative therapies, and its US approval by the FDA in 2009 mandated the creation of a drug registry to monitor patients for visual deficits.

    Mechanism of Action

    Gamma-aminobutyric acid (GABA) is the major inhibitory transmitter throughout the central nervous system, and the potentiation of GABAergic neurotransmission is therefore a crucial mechanism through which antiepileptic agents may combat the pathologic excitatory neurotransmission seen in epilepsy. Vigabatrin increases concentrations of GABA in the central nervous system by irreversibly inhibiting the enzymes responsible for its metabolism to succinic semialdehyde: gamma-aminobutyric acid transaminase (GABA-T).

    Pharmacodynamics

    Vigabatrin is an antiepileptic agent chemically unrelated to other anticonvulsants. Vigabatrin prevents the metabolism of GABA by irreversibly inhibiting GABA transaminase (GABA-T). As vigabatrin is an irreversible inhibitor of gamma-aminobutyric acid transaminase (GABA-T), its duration of effect is thought to be dependent on the rate of GABA-T re-synthesis rather than on the rate of drug elimination.

    Metabolism

    Vigabatrin is not metabolized to any significant extent.

    Absorption

    Absorption following oral administration is essentially complete. The Tmax is approximately 2.5 hours in infants (5m - 2y) and 1 hour in all other age groups.

    Indication

    Vigabatrin is indicated as adjunctive therapy in the treatment of refractory complex partial seizures in patients 2 years of age and older who have had inadequate responses to multiple previous treatments (i.e. not to be used for first-line therapy). It is also indicated as monotherapy in the treatment of infantile spasms in patients between 1 month and 2 years of age for whom the potential benefits outweigh the risk of vision loss.

    Half-life

    The terminal half-life of vigabatrin is approximately 5.7 hours for infants (5m - 2y), 6.8 hours for children (3y - 9y), 9.5 hours for adolescents (10y - 16y), and 10.5 h for adults.

    Protein Binding

    Vigabatrin does not bind to plasma proteins.

    Elimination

    Approximately 95% of the drug is eliminated in the urine within 72 hours of administration, of which ~80% is unchanged parent drug.

    Volume of Distribution

    Vigabatrin is widely distributed throughout the body with a mean steady-state volume of distribution of 1.1 L/kg.

    Clearance

    The oral clearance of vigabatrin is 2.4 L/h for infants (5m - 2y), 5.1 L/h for children (3y - 9y), 5.8 L/h for adolescents (10y - 16y), and 7 L/h for adults.

    Toxicity

    PubChem DrugBank

    Visual field defects, including permanent vision loss, have been reported in infants, children, and adults receiving vigabatrin. Based on clinical studies in adults, bilateral concentric visual field constriction ranging in severity from mild to severe may occur in 30% or more of patients receiving the drug. Signs and Symptoms of Overdose Vigabatrin toxicity typically develops gradually as a result of prolonged treatment. One case of acute toxicity involved a 25-year-old patient who attempted suicide by consuming 120 vigabatrin tablets (500 mg each).

    LD50

    • LD50, oral, rat: 3000 mg/kg

    Carcinogenicity

    No indication of carcinogenicity to humans (not listed by IARC).

    Liver injury risk

    Ambiguous (limited data)

    FDA LiverTox / DILIrank. Reflects published case reports of liver injury, not absolute risk.

    Health effects (PubChem excerpts)

    May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 3d Half tolerance 8d Baseline ~14d
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