Tracazolate

Summary

Tracazolate (ICI-136,753) is an anxiolytic drug which is used in scientific research. It is a pyrazolopyridine derivative, most closely related to pyrazolopyrimidine drugs such as zaleplon, and is one of a structurally diverse group of drugs known as the nonbenzodiazepines which act at the same receptor targets as benzodiazepines but have distinct chemical structures.[1]

Tracazolate
Clinical data
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • Ethyl 4-(butylamino)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
CAS Number
  • 41094-88-6
PubChem CID
  • 5522
IUPHAR/BPS
  • 5467
ChemSpider
  • 5321
UNII
  • NH0HPL3U1T
KEGG
  • D06200
ChEBI
  • CHEBI:92596
ChEMBL
  • ChEMBL84567
CompTox Dashboard (EPA)
  • DTXSID3046956 Edit this at Wikidata
ECHA InfoCard100.050.178 Edit this at Wikidata
Chemical and physical data
FormulaC16H24N4O2
Molar mass304.394 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(OCC)c1c(c2c(nc1C)n(nc2)CC)NCCCC
  • InChI=1S/C16H24N4O2/c1-5-8-9-17-14-12-10-18-20(6-2)15(12)19-11(4)13(14)16(21)22-7-3/h10H,5-9H2,1-4H3,(H,17,19)
  • Key:PCTRYMLLRKWXGF-UHFFFAOYSA-N

Tracazolate has primarily anxiolytic and anticonvulsant effects, with sedative and muscle relaxant effects only appearing at higher doses.[2] It has a unique receptor binding profile involving allosteric modulation of several GABAA receptor subtypes, being selective for GABAA receptors containing α1 and β3 subunits, but exhibiting different effects depending on the third type of subunit making up the receptor complex.[3]

See also edit

References edit

  1. ^ Patel JB, Malick JB, Salama AI, Goldberg ME (October 1985). "Pharmacology of pyrazolopyridines". Pharmacology, Biochemistry, and Behavior. 23 (4): 675–80. doi:10.1016/0091-3057(85)90436-8. PMID 2866547. S2CID 31584179.
  2. ^ Patel JB, Malick JB (March 1982). "Pharmacological properties of tracazolate: a new non-benzodiazepine anxiolytic agent". European Journal of Pharmacology. 78 (3): 323–33. doi:10.1016/0014-2999(82)90034-6. PMID 6121711.
  3. ^ Thompson SA, Wingrove PB, Connelly L, Whiting PJ, Wafford KA (April 2002). "Tracazolate reveals a novel type of allosteric interaction with recombinant gamma-aminobutyric acid(A) receptors". Molecular Pharmacology. 61 (4): 861–9. doi:10.1124/mol.61.4.861. PMID 11901225. S2CID 7039885.