Tracazolate

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	41094-88-6
PubChem CID	5522
IUPHAR/BPS	5467
ChemSpider	5321
UNII	NH0HPL3U1T
KEGG	D06200
ChEBI	CHEBI:92596
ChEMBL	ChEMBL84567
CompTox Dashboard (EPA)	DTXSID3046956
ECHA InfoCard	100.050.178
Chemical and physical data
Formula	C16H24N4O2
Molar mass	304.394 g·mol−1
3D model (JSmol)	Interactive image
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 (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 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 GABA_A receptor subtypes, being selective for GABA_A receptors containing α1 and β3 subunits, but exhibiting different effects depending on the third type of subunit making up the receptor complex.^[3]

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.

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