Tracazolate

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]

Not to be confused with cartazolate.
Tracazolate
Clinical data
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • Ethyl 4-(butylamino)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.050.178
Chemical and physical data
FormulaC16H24N4O2
Molar mass304.394 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC)c1c(c2c(nc1C)n(nc2)CC)NCCCC
InChI
  • 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

References
  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.
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