Chemistry:N-Benzoyl-GABA

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N-Benzoyl-GABA
Clinical data
Other namesN-Benzoyl-γ-aminobutyric acid; N-Benzoyl-gamma-aminobutyric acid
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChEMBL
Chemical and physical data
FormulaC11H13NO3
Molar mass207.229 g·mol−1
3D model (JSmol)

N-Benzoyl-GABA is a claimed GABA receptor agonist and derivative of the inhibitory neurotransmitter γ-aminobutyric acid (GABA).[1][2][3][4] It is said to be a lipophilic prodrug of GABA that in contrast to GABA itself is able to cross the blood–brain barrier.[1][2][5][4] The drug produces anticonvulsant effects in rodents.[4] It was first described in the scientific literature by 1978.[4]

See also

References

  1. ↑ 1.0 1.1 "Drug Delivery to the Brain by Blood-Brain Barrier Circumvention and Drug Modification". Implications of the Blood-Brain Barrier and Its Manipulation. Boston, MA: Springer US. 1989. pp. 311–367. doi:10.1007/978-1-4613-0701-3_12. ISBN 978-1-4612-8039-2. "The development of carboxyl-linked prodrugs for brain delivery has met with mixed success. Considerable effort has been channeled into the evolution of GABA-mimetics that are capable of entering the brain. The central inhibitory neurotransmitter GABA (Fig. 19) is a zwitterion at physiologic pH, pKa 4.0 and 10.7, and minimally penetrates the BBB. A variety of potential GABA prodrugs have been synthesized to mask the amino group by acylation 79; these have included N-pivaloyl and N-benzoyl-GABA. 82 Both compounds appeared to enter the brains of rats in significant amounts, reaching peak concentrations at 30 and 5 min, respectively. However, the in vivo enzymatic cleavage of such amides has proved difficult in humans." 
  2. ↑ 2.0 2.1 "Amino acid neurotransmitters and new approaches to anticonvulsant drug action". Epilepsia 25 Suppl 2: S140–S149. 1984. doi:10.1111/j.1528-1157.1984.tb05646.x. PMID 6146519. 
  3. ↑ "Synthesis and study of psychotropic and hypotensive properties of new picamilon derivatives". Pharmaceutical Chemistry Journal 31 (10): 536–539. 1997. doi:10.1007/BF02464261. ISSN 0091-150X. 
  4. ↑ 4.0 4.1 4.2 4.3 "Properties of two derivatives of gamma-aminobutyric acid (GABA) capable of abolishing Cardiazol- and bicuculline-induced convulsions in the rat". Archives Internationales de Pharmacodynamie et de Therapie 235 (1): 73–85. September 1978. PMID 736693. 
  5. ↑ "N-methyl phenylalanine-rich peptides as highly versatile blood-brain barrier shuttles". Journal of Medicinal Chemistry 53 (6): 2354–2363. March 2010. doi:10.1021/jm901654x. PMID 20170117. "Galzigna et al.41 demonstrated that N-benzoyl-GABA and N-pivaloyl-GABA, in contrast to GABA, crossed the BBB in rats and were cleaved enzymatically to release GABA.". 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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