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Wikipedia - Tiagabine

Tiagabine
Systematic (IUPAC) name
(R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl] piperidine-3-carboxylic acid
Identifiers
CAS number 115103-54-3
ATC code N03AG06
PubChem CID 60648
DrugBank APRD00344
Chemical data
Formula C20H25NO2S2 
Mol. mass 375.55 g/mol
Pharmacokinetic data
Bioavailability 90%
Protein binding 96%
Metabolism Hepatic (CYP450 system)
Half-life 7-9 hours
Excretion Fecal and renal
Therapeutic considerations
Pregnancy cat. B3 (Au), C (U.S.)
Legal status POM (UK), ?-only (U.S.)
Routes Oral
 YesY(what is this?)  (verify)

Tiagabine (pronounced /ta?'æg?bi?n/[1]) is an anti-convulsive medication produced by Cephalon and marketed under the brand name Gabitril. The drug was discovered at Novo Nordisk in Denmark in 1988 and was co-developed with Abbott. After a period of co-promotion, Cephalon licensed Tiagabine from Abbott/Novo and now is the exclusive producer. The medication is also used in the treatment of panic disorder, as are a few other anticonvulsants.

Contents

[edit] Pharmacology

It is believed that the pharmacology is related to its ability, documented in in vitro experiments, to enhance the activity of gamma aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. These experiments have shown that tiagabine binds to recognition sites associated with the GABA uptake carrier. It is thought that, by this action, tiagabine blocks GABA uptake into presynaptic neurons, permitting more GABA to be available for receptor binding on the surfaces of post-synaptic cells. Evidence is available that it operates as a selective GABA reuptake inhibitor.[1]

[edit] Side effects

Tiagabine's most common side effects include confusion, difficulty speaking clearly/stuttering, mild sedation, and in doses over 8 mg, a tingling sensation (paresthesia) in the body's extremities, particularly the hands and fingers.

With overdoses in the range of 20-40 mg or more it will cause extreme sedation, temporary retardation, muscle tremors and spasms, uncontrollable bodily tremors, retrograde and anterograde amnesia, thrashing, screaming, flailing and extreme hostility, unconsciousness with seizures or seizure-like symptoms. Upon consciousness: extreme confusion with an inability to form coherent sentences, express ideas, or do the most basic activities for several hours. [original research?] Unlike the benzodiazepines Tiagabine (Gabitril) has been shown to have no recreation value and any euphoria is most likely a placebo effect or because of consumption with alcohol.

[edit] Synthesis

Tiagabine Rxn.png

Andersen, Knud Erik; Braestrup, Claus; Groenwald, Frederik C.; Joergensen, Anker S.; Nielsen, Erik B.; Sonnewald, Ursula; Soerensen, Per O.; Suzdak, Peter D. et al. (1993). "The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate". Journal of Medicinal Chemistry 36: 1716. doi:10.1021/jm00064a005. 

[edit] References

  1. ^ Pollack MH, Roy-Byrne PP, Van Ameringen M, et al. (November 2005). "The selective GABA reuptake inhibitor tiagabine for the treatment of generalized anxiety disorder: results of a placebo-controlled study". The Journal of clinical psychiatry 66 (11): 1401–8. doi:10.4088/JCP.v66n1109. PMID 16420077. http://article.psychiatrist.com/?ContentType=START&ID=10001907. 

[edit] External links


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Anticonvulsants (N03)
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Primarily sodium
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Unknown/multiple/
unsorted
#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III
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Anxiolytics (N05B)
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a2d VDCC Blockers
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#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

M: PSO/PSI

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M: PSO/PSI

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc, drug(N5A/5B/5C/6A/6B/6D)
Retrieved from "http://en.wikipedia.org/wiki/Tiagabine"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tiagabine".

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