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Chemistry

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Also known as: 4-aminohex-5-enoic acid, 60643-86-9, Sabril, 68506-86-5, 4-amino-5-hexenoic acid, Gamma-vinyl gaba
Molecular Formula
C6H11NO2
Molecular Weight
129.16  g/mol
InChI Key
PJDFLNIOAUIZSL-UHFFFAOYSA-N
FDA UNII
GR120KRT6K

Vigabatrin
An analogue of GAMMA-AMINOBUTYRIC ACID. It is an irreversible inhibitor of 4-AMINOBUTYRATE TRANSAMINASE, the enzyme responsible for the catabolism of GAMMA-AMINOBUTYRIC ACID and is used as an anticonvulsant. (From Martindale The Extra Pharmacopoeia, 31st ed)
Vigabatrin is an Anti-epileptic Agent.
1 2D Structure

Vigabatrin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-aminohex-5-enoic acid
2.1.2 InChI
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
2.1.3 InChI Key
PJDFLNIOAUIZSL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C=CC(CCC(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
GR120KRT6K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gamma Vinyl Gaba

2. Gamma Vinyl Gamma Aminobutyric Acid

3. Gamma-vinyl-gaba

4. Gamma-vinyl-gamma-aminobutyric Acid

5. Sabril

6. Sabrilex

2.3.2 Depositor-Supplied Synonyms

1. 4-aminohex-5-enoic Acid

2. 60643-86-9

3. Sabril

4. 68506-86-5

5. 4-amino-5-hexenoic Acid

6. Gamma-vinyl Gaba

7. Vigabatrine

8. Gamma-vinyl-gaba

9. 5-hexenoic Acid, 4-amino-

10. Gamma Vinyl Gaba

11. Vigabatrinum

12. Mdl-71754

13. 4-aminohexenoic Acid

14. Gamma-vinyl-gamma-aminobutyric Acid

15. Rmi-71754

16. Cpp-109

17. Gvg

18. Mdl 71,754

19. Cpp109

20. (+/-)-vigabatrin

21. Vinyl Gamma-aminobutyric Acid

22. Gr120krt6k

23. (+/-)-gamma-vinyl Gaba

24. Chembl89598

25. Chebi:63638

26. Vigabatrine [french]

27. Vigabatrinum [latin]

28. (+/-)-4-aminohex-5-enoic Acid

29. Vigabatrina [spanish]

30. Ncgc00016087-06

31. Vigabatrina

32. Sabrilex

33. 4-aminohex-5-enoic Acid/s(+)-gamma-vigabatrin

34. Sabril (tn)

35. Vigabatrin [usan:inn:ban]

36. Rmi-71890

37. Mdl 71754

38. Rmi 71754

39. Hexenoic Acid, 4-amino

40. Sr-01000075653

41. Unii-gr120krt6k

42. (+-)-gamma-vinyl Gaba

43. 4-amino-hex-5-enoic Acid

44. (+/-)-gamma-vinyl-gaba

45. Kigabeq

46. Rac-vigabatrin

47. Mfcd00274076

48. (1)-4-aminohex-5-enoic Acid

49. Cpp 109

50. Vigabatrin Solution

51. Vigabatrin [inn]

52. Prestwick_837

53. Einecs 270-929-6

54. Cas-60643-86-9

55. Mfcd00274577

56. .gamma.-vinyl Gaba

57. .gamma.-vinyl-gaba

58. Spectrum_000368

59. 4-amino-5-hexenoicacid

60. Specplus_000664

61. Vigabatrin [mi]

62. (y)-gamma-vinyl Gaba

63. Vigabatrin [jan]

64. Prestwick0_000501

65. Prestwick1_000501

66. Prestwick2_000501

67. Prestwick3_000501

68. Spectrum3_001825

69. Vigabatrin [usan]

70. (?)-gamma-vinyl Gaba

71. Vigabatrin [vandf]

72. Biomol-nt_000247

73. V 8261

74. Vigabatrin [mart.]

75. Dsstox_cid_21153

76. Dsstox_rid_79637

77. Vigabatrin [usp-rs]

78. Vigabatrin [who-dd]

79. Dsstox_gsid_41153

80. Lopac0_001277

81. M071754

82. Schembl26714

83. Bspbio_000421

84. Bspbio_003469

85. Kbioss_000848

86. Vigabatrin (jan/usp/inn)

87. (a+/-)-gamma-vinyl Gaba

88. Divk1c_006760

89. Spectrum1502036

90. (+/-)-?-vinyl Gaba

91. Spbio_002342

92. Bpbio1_000465

93. Bpbio1_000925

94. Gtpl4821

95. Dtxsid4041153

96. Vigabatrin [orange Book]

97. Vinyl .gamma.-aminobutyric Acid

98. Hsdb 8395

99. Kbio1_001704

100. Kbio2_000848

101. Kbio2_003416

102. Kbio2_005984

103. Kbio3_002973

104. Vigabatrin, (+/-)-

105. Amy6474

106. Vigabatrin [ep Monograph]

107. S(+)-4-aminohexenoicacid

108. Hms1569f03

109. Hms2094m21

110. Hms2096f03

111. Hms3263p16

112. Vigabatrin [usp Monograph]

113. Bcp16220

114. Tox21_110301

115. Tox21_501277

116. Bdbm50118886

117. Akos015854596

118. Ccg-205350

119. Cs-0791

120. Db01080

121. Lp01277

122. Sdccgsbi-0051243.p004

123. .gamma.-vinyl-.gamma.-aminobutyric Acid

124. Ncgc00016087-03

125. Ncgc00016087-04

126. Ncgc00016087-05

127. Ncgc00016087-07

128. Ncgc00016087-08

129. Ncgc00016087-09

130. Ncgc00016087-11

131. Ncgc00016087-22

132. Ncgc00024802-02

133. Ncgc00024802-03

134. Ncgc00024802-04

135. Ncgc00024802-05

136. Ncgc00024802-06

137. Ncgc00261962-01

138. As-11778

139. Hy-15399

140. Sy263247

141. Sbi-0051243.p003

142. ( Inverted Question Mark)-gamma-vinyl Gaba

143. Db-117820

144. Ab00053309

145. Eu-0101277

146. Ft-0675811

147. Ft-0675812

148. Ft-0700968

149. Gamma-vinyl Gaba; 4-amino-5-hexenoic Acid

150. C07500

151. D00535

152. Ab00053309_04

153. A853593

154. Q421663

155. Q-201924

156. Sr-01000075653-1

157. Sr-01000075653-4

158. Sr-01000075653-6

159. ( Inverted Exclamation Marka)-4-aminohex-5-enoic Acid

160. Brd-a07893380-001-01-6

161. Z2235791448

162. Vigabatrin, European Pharmacopoeia (ep) Reference Standard

163. Vigabatrin, United States Pharmacopeia (usp) Reference Standard

164. Vigabatrin Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 129.16 g/mol
Molecular Formula C6H11NO2
XLogP3-2.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass129.078978594 g/mol
Monoisotopic Mass129.078978594 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count9
Formal Charge0
Complexity112
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameSabril
PubMed HealthVigabatrin (By mouth)
Drug ClassesAnticonvulsant
Drug LabelSABRIL (vigabatrin) is an oral antiepileptic drug and is available as white film-coated 500 mg tablets and as a white to off-white granular powder for oral solution in packets of 500 mg. The chemical name of vigabatrin, a racemate consisting of two e...
Active IngredientVigabatrin
Dosage FormTablet; For solution
RouteOral
Strength500mg; 500mg/packet
Market StatusPrescription
CompanyLundbeck

2 of 2  
Drug NameSabril
PubMed HealthVigabatrin (By mouth)
Drug ClassesAnticonvulsant
Drug LabelSABRIL (vigabatrin) is an oral antiepileptic drug and is available as white film-coated 500 mg tablets and as a white to off-white granular powder for oral solution in packets of 500 mg. The chemical name of vigabatrin, a racemate consisting of two e...
Active IngredientVigabatrin
Dosage FormTablet; For solution
RouteOral
Strength500mg; 500mg/packet
Market StatusPrescription
CompanyLundbeck

4.2 Therapeutic Uses

Anticonvulsants; Enzyme Inhibitors; GABA Agents

National Library of Medicine's Medical Subject Headings. Vigabatrin. Online file (MeSH, 2017). Available from, as of Oct 4, 2017: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Vigabatrin is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of August 30, 2017: https://clinicaltrials.gov/


Sabril is indicated as adjunctive therapy for adults and pediatric patients 10 years of age and older with refractory complex partial seizures who have inadequately responded to several alternative treatments and for whom the potential benefits outweigh the risk of vision loss. Sabril is not indicated as a first line agent for complex partial seizures. /Included in US product label/

NIH; DailyMed. Current Medication Information for Sabril (Vigabatrin Tablet, Film Coated) (Updated: April 2017). Available from, as of October 19, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5d389d2-d0e1-4395-a2a2-b552808e7f98


Sabril is indicated as monotherapy for pediatric patients with infantile spasms 1 month to 2 years of age for whom the potential benefits outweigh the potential risk of vision loss. /Included in US product label/

NIH; DailyMed. Current Medication Information for Sabril (Vigabatrin Tablet, Film Coated) (Updated: April 2017). Available from, as of October 19, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5d389d2-d0e1-4395-a2a2-b552808e7f98


4.3 Drug Warning

/BOXED WARNING/ WARNING: PERMANENT VISION LOSS. Sabril can cause permanent bilateral concentric visual field constriction, including tunnel vision that can result in disability. In some cases, Sabril also can damage the central retina and may decrease visual acuity. The onset of vision loss from Sabril is unpredictable, and can occur within weeks of starting treatment or sooner, or at any time after starting treatment, even after months or years. Symptoms of vision loss from Sabril are unlikely to be recognized by patients or caregivers before vision loss is severe. Vision loss of milder severity, while often unrecognized by the patient or caregiver, can still adversely affect function. The risk of vision loss increases with increasing dose and cumulative exposure, but there is no dose or exposure known to be free of risk of vision loss. Vision assessment is recommended at baseline (no later than 4 weeks after starting Sabril), at least every 3 months during therapy, and about 3 to 6 months after the discontinuation of therapy. Once detected, vision loss due to Sabril is not reversible. It is expected that, even with frequent monitoring, some patients will develop severe vision loss. Consider drug discontinuation, balancing benefit and risk, if visual loss is documented. Risk of new or worsening vision loss continues as long as Sabril is used. It is possible that vision loss can worsen despite discontinuation of Sabril. Because of the risk of vision loss, Sabril should be withdrawn from patients with refractory complex partial seizures who fail to show substantial clinical benefit within 3 months of initiation and within 2-4 weeks of initiation for patients with infantile spasms, or sooner if treatment failure becomes obvious. Patient response to and continued need for Sabril should be periodically reassessed. Sabril should not be used in patients with, or at high risk of, other types of irreversible vision loss unless the benefits of treatment clearly outweigh the risks. Sabril should not be used with other drugs associated with serious adverse ophthalmic effects such as retinopathy or glaucoma unless the benefits clearly outweigh the risks. Use the lowest dosage and shortest exposure to Sabril consistent with clinical objectives. Because of the risk of permanent vision loss, Sabril is available only through a restricted program under a Risk Evaluation and Mitigation Strategy (REMS) called the Vigabatrin REMS Program

NIH; DailyMed. Current Medication Information for Sabril (Vigabatrin Tablet, Film Coated) (Updated: April 2017). Available from, as of October 19, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5d389d2-d0e1-4395-a2a2-b552808e7f98


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. Severe cases may be characterized by tunnel vision to within 10 degrees of visual fixation, which can lead to disability. In some cases, vigabatrin can also damage the central retina and decrease visual acuity. Because vision assessment may be difficult in infants and children, the frequency and extent of vision loss is poorly characterized in such patients; therefore, the understanding of the risk is mainly based on adult experience with the drug. The possibility that vigabatrin-induced vision loss may be more common, more severe, or have more functional consequences in infants and children than in adults cannot be excluded.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2420-1


The onset and progression of vision loss with vigabatrin are unpredictable and can occur within weeks of beginning treatment or sooner or at any time after starting therapy, even after months or years. In addition, vision loss may develop or worsen precipitously between vision assessments. Symptoms of vigabatrin-associated vision loss are unlikely to be recognized by patients or caregivers before the impairment is severe. Vision loss of milder severity that is often unrecognized by the patient or caregiver can still adversely affect function. Once detected, vigabatrin-induced visual field defects are irreversible and will not improve even after the drug is discontinued. In addition, it is possible that further impairment of vision may occur following drug discontinuance. Risk of vision loss increases with increasing dosages and cumulative exposure to vigabatrin; however, no dosage or exposure to the drug is known to be free of the risk of vision loss. Some studies have suggested that smoking, age, and male gender are possible risk factors for developing visual field defects.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2421


In patients with infantile spasms, vigabatrin therapy should be withdrawn if a substantial clinical benefit is not observed within 2-4 weeks of initiating the drug. If, in the clinical judgment of the prescribing clinician, evidence of treatment failure becomes obvious earlier than 2-4 weeks, vigabatrin treatment should be discontinued at that time.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2421


For more Drug Warnings (Complete) data for Vigabatrin (25 total), please visit the HSDB record page.


4.4 Drug 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.


Kigabeq is indicated in infants and children from 1 month to less than 7 years of age for:

- Treatment in monotherapy of infantile spasms (West's syndrome).

- Treatment in combination with other antiepileptic medicinal products for patients with resistant partial epilepsy (focal onset seizures) with or without secondary generalisation, that is where all other appropriate medicinal product combinations have proved inadequate or have not been tolerated.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


GABA Agents

Substances used for their pharmacological actions on GABAergic systems. GABAergic agents include agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function. (See all compounds classified as GABA Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
VIGABATRIN
5.3.2 FDA UNII
GR120KRT6K
5.3.3 Pharmacological Classes
Anti-epileptic Agent [EPC]
5.4 ATC Code

N03AG04


N03AG04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AG - Fatty acid derivatives

N03AG04 - Vigabatrin


5.5 Absorption, Distribution and Excretion

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.


Route of 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.


Drug transporters in various tissues, such as intestine, kidney, liver and brain, are recognized as important mediators of absorption, distribution, metabolism and excretion of drug substances. This review gives a current status on the transporter(s) mediating the absorption, distribution, metabolism and excretion properties of the anti-epileptic drug substance vigabatrin. For orally administered drugs, like vigabatrin, the absorption from the intestine is a prerequisite for the bioavailability. Therefore, transporter(s) involved in the intestinal absorption of vigabatrin in vitro and in vivo are discussed in detail. Special focus is on the contribution of the proton-coupled amino acid transporter 1 (PAT1) for intestinal vigabatrin absorption. Furthermore, the review gives an overview of the pharmacokinetic parameters of vigabatrin across different species and drug-food and drug-drug interactions involving vigabatrin.

PMID:25337649 Nohr MK et al; Ther Deliv 5 (8): 927-42 (2014)


The aims were to determine blood-brain barrier penetration and brain extracellular pharmacokinetics for the anticonvulsant vigabatrin (VGB; gamma-vinyl-gamma-aminobutyric acid) in brain extracellular fluid and plasma from severe traumatic brain injury (TBI) patients, and to measure the response of gamma-aminobutyric acid (GABA) concentration in brain extracellular fluid. Severe TBI patients (n = 10) received VGB (0.5 g enterally, every 12 hr). Each patient had a cerebral microdialysis catheter; two patients had a second catheter in a different region of the brain. Plasma samples were collected 0.5 hr before and 2, 4 and 11.5 hr after the first VGB dose. Cerebral microdialysis commenced before the first VGB dose and continued through at least three doses of VGB. Controls were seven severe TBI patients with microdialysis, without VGB. After the first VGB dose, the maximum concentration of VGB (Cmax) was 31.7 (26.9-42.6) umol/L (median and interquartile range for eight patients) in plasma and 2.41 (2.03-5.94) umol/L in brain microdialysates (nine patients, 11 catheters), without significant plasma-brain correlation. After three doses, median Cmax in microdialysates increased to 5.22 (4.24-7.14) umol/L (eight patients, 10 catheters). Microdialysate VGB concentrations were higher close to focal lesions than in distant sites. Microdialysate GABA concentrations increased modestly in some of the patients after VGB administration. Vigabatrin, given enterally to severe TBI patients, crosses the blood-brain barrier into the brain extracellular fluid, where it accumulates with multiple dosing. Pharmacokinetics suggest delayed uptake from the blood.

PMID:24802902 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4243872 Shannon RJ et al; Br J Clin Pharmacol 78 (5): 981-95 (2014)


/MILK/ Vigabatrin distributes into milk, probably in small amounts.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2422


The aim of the study was to investigate the intestinal transport mechanisms responsible for vigabatrin absorption in rats by developing a population pharmacokinetic (PK) model of vigabatrin oral absorption. The PK model was used to investigate whether vigabatrin absorption was carrier-mediated and if the proton-coupled amino acid transporter 1 (PAT1) was involved in the absorption processes. Vigabatrin (0.3-300 mg/kg) was administered orally or intravenously to Sprague Dawley rats in the absence or presence of PAT1-ligands l-proline, l-tryptophan or sarcosine. The PK profiles of vigabatrin were described by mechanistic non-linear mixed effects modelling, evaluating PAT1-ligands as covariates on the PK parameters with a full covariate modelling approach. The oral absorption of vigabatrin was adequately described by a Michaelis-Menten type saturable absorption. Using a Michaelis constant of 32.8 mM, the model estimated a maximal oral absorption rate (Vmax) of 64.6mmol/min and dose-dependent bioavailability with a maximum of 60.9%. Bioavailability was 58.5-60.8% at 0.3-30 mg/kg doses, but decreased to 46.8% at 300 mg/kg. Changes in oral vigabatrin PK after co-administration with PAT1-ligands was explained by significant increases in the apparent Michaelis constant. Based on the mechanistic model, a high capacity low affinity carrier is proposed to be involved in intestinal vigabatrin absorption. PAT1-ligands increased the Michaelis constant of vigabatrin after oral co-administration indicating that this carrier could be PAT1.

PMID:25562534 Nohr MK et al; Eur J Pharm Sci 69:10-8 (2015)


For more Absorption, Distribution and Excretion (Complete) data for Vigabatrin (10 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Vigabatrin is not metabolized to any significant extent.


Vigabatrin is not significantly metabolized ... .

NIH; DailyMed. Current Medication Information for Sabril (Vigabatrin Tablet, Film Coated) (Updated: April 2017). Available from, as of October 19, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5d389d2-d0e1-4395-a2a2-b552808e7f98


5.7 Biological 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.


The terminal half-life of vigabatrin is about 5.7 hours for infants (5 months - 2 years), 9.5 hours for children (10 years - 16 years), and 10.5 hours for adults.

NIH; DailyMed. Current Medication Information for Sabril (Vigabatrin Tablet, Film Coated) (Updated: April 2017). Available from, as of October 19, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5d389d2-d0e1-4395-a2a2-b552808e7f98


5.8 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).


Vigabatrin is a structural analog of gamma-aminobutyric acid (GABA), the primary inhibitory neurotransmitter in the CNS. Although the exact mechanism of vigabatrin's antiseizure effect is unknown, it is thought to be related to the drug's action as a preferential and irreversible inhibitor of GABA transaminase (GABA-T), which is the enzyme responsible for the degradation of GABA and the resultant increase in GABA concentrations in the CNS. Vigabatrin is commercially available as a racemic mixture of 2 enantiomers; the S enantiomer is pharmacologically active and the R enantiomer is inactive.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2423


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06-Feb-2021
24-Jul-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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