Isoguvacine

Isoguvacine
Clinical data
Drug class	GABAA receptor agonist
Identifiers
	IUPAC name 1,2,3,6-tetrahydropyridine-4-carboxylic acid;
CAS Number	64603-90-3;
PubChem CID	3765;
IUPHAR/BPS	4226;
ChemSpider	3633;
UNII	YTF580771Y;
ChEMBL	ChEMBL39071;
CompTox Dashboard (EPA)	DTXSID30214855 ;
ECHA InfoCard	100.150.537
Chemical and physical data
Formula	C6H9NO2
Molar mass	127.143 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)/C1=C/CNCC1;

Isoguvacine is a GABA_A receptor agonist used in scientific research.^[1] It is a highly charged zwitterion and is unable to enter the central nervous system or produce central mediated effects.^[2]^[3] There has been interest in centrally penetrant isoguvacine prodrugs for potential medical use.^[3]

References

↑ Wahab A, Heinemann U, Albus K (October 2009). "Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures". Epilepsy Research. 86 (2–3): 113–23. doi:10.1016/j.eplepsyres.2009.05.008. PMID 19535226. S2CID 32999271.
↑ Wafford KA, Ebert B (February 2006). "Gaboxadol--a new awakening in sleep". Curr Opin Pharmacol. 6 (1): 30–36. doi:10.1016/j.coph.2005.10.004. PMID 16368265. Early studies demonstrated that the highly charged zwitterions isoguvacine and P4S were unable to enter the CNS or exert any pharmacological activity, whereas muscimol and (to an even larger extent) gaboxadol produced observable changes in behaviour after systemic application [25].
1 2 Krogsgaard-Larsen P, Arnt J (1979). "GABA receptor agonists: relationship between structure and biological activity in vivo and in vitro". GABA—Biochemistry and CNS Functions. Advances in Experimental Medicine and Biology. Vol. 123. Boston, MA: Springer US. pp. 303–321. doi:10.1007/978-1-4899-5199-1. ISBN 978-1-4899-5201-1. PMID 390994. Isoguvacine apparently does not easily penetrate the bloodbrain barrier after systemic administration. Hence, a variety of its derivatives have been developed as part of a systematic search for "pro-drugs" of isoguvacine. The goal of this approach is to develop a non-toxic derivative of isoguvacine, which easily penetrates into the brain after systemic administration and which is subsequently hydrolyzed therein to give isoguvacine. A "pro-drug" of isoguvacine which meets these pharmacokinetic requirements may be of pharmacological and possibly of therapeutic interest.

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[pmid19535226-1] Wahab A, Heinemann U, Albus K (October 2009). "Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures". Epilepsy Research. 86 (2–3): 113–23. doi:10.1016/j.eplepsyres.2009.05.008. PMID 19535226. S2CID 32999271.

[WaffordEbert2006-2] Wafford KA, Ebert B (February 2006). "Gaboxadol--a new awakening in sleep". Curr Opin Pharmacol. 6 (1): 30–36. doi:10.1016/j.coph.2005.10.004. PMID 16368265. Early studies demonstrated that the highly charged zwitterions isoguvacine and P4S were unable to enter the CNS or exert any pharmacological activity, whereas muscimol and (to an even larger extent) gaboxadol produced observable changes in behaviour after systemic application [25].

[Krogsgaard-LarsenArnt1979-3] 1 2 Krogsgaard-Larsen P, Arnt J (1979). "GABA receptor agonists: relationship between structure and biological activity in vivo and in vitro". GABA—Biochemistry and CNS Functions. Advances in Experimental Medicine and Biology. Vol. 123. Boston, MA: Springer US. pp. 303–321. doi:10.1007/978-1-4899-5199-1. ISBN 978-1-4899-5201-1. PMID 390994. Isoguvacine apparently does not easily penetrate the bloodbrain barrier after systemic administration. Hence, a variety of its derivatives have been developed as part of a systematic search for "pro-drugs" of isoguvacine. The goal of this approach is to develop a non-toxic derivative of isoguvacine, which easily penetrates into the brain after systemic administration and which is subsequently hydrolyzed therein to give isoguvacine. A "pro-drug" of isoguvacine which meets these pharmacokinetic requirements may be of pharmacological and possibly of therapeutic interest.

[1]

[2]

[3]

See also

References