Cartazolate

Cartazolate

Cartazolate
Systematic (IUPAC) name
ethyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII  YesY
ChEMBL
Chemical data
Formula C15H22N4O2 
Mol. mass 290.36 g/mol

Cartazolate (SQ-65,396) is a drug of the pyrazolopyridine class. It acts as a GABAA receptor positive allosteric modulator at the barbiturate binding site of the complex and has anxiolytic effects in animals.[1][2][3][4] It is also known to act as an adenosine antagonist at the A1 and A2 subtypes and as a phosphodiesterase inhibitor.[5][6] Cartazolate was tested in human clinical trials and was found to be efficacious for anxiety but was never marketed.[7] It was developed by a team at E.R. Squibb and Sons in the 1970s.[8]

Synthesis

Cartazolate and Etazolate synthesis: E.R. SQUIBB & SONS, INC., NEW YORK, N.Y., US. DE 2123318 
  • ACETONE HYDRAZONE:[9]

See also

References

  1. ^ Placheta P, Karobath M (March 1980). "In vitro modulation by SQ 20009 and SQ 65396 of GABA receptor binding in rat CNS membranes". European Journal of Pharmacology 62 (2-3): 225–8.  
  2. ^ Supavilai P, Karobath M (March 1981). "Action of pyrazolopyridines as modulators of [3H]flunitrazepam binding to the gaba/benzodiazepine receptor complex of the cerebellum". European Journal of Pharmacology 70 (2): 183–93.  
  3. ^ Leeb-Lundberg F, Snowman A, Olsen RW (May 1981). "Perturbation of benzodiazepine receptor binding by pyrazolopyridines involves picrotoxinin/barbiturate receptor sites". Journal of Neuroscience 1 (5): 471–7.  
  4. ^ Bristow DR, Martin IL (March 1990). "Biochemical characterization of an isolated and functionally reconstituted gamma-aminobutyric acid/benzodiazepine receptor". Journal of Neurochemistry 54 (3): 751–61.  
  5. ^ Daly JW, Hong O, Padgett WL, Shamim MT, Jacobson KA, Ukena D (February 1988). "Non-xanthine heterocycles: activity as antagonists of A1- and A2-adenosine receptors".  
  6. ^ Wachtel H (1982). "Characteristic behavioural alterations in rats induced by rolipram and other selective adenosine cyclic 3', 5'-monophosphate phosphodiesterase inhibitors". Psychopharmacology 77 (4): 309–16.  
  7. ^ O'Brien, Robert (1986). Receptor binding in drug research. New York: Dekker. p. 519.  
  8. ^ US Patent 3966746 Amino derivatives of pyrazolopyridine carboxamides
  9. ^ http://www.orgsyn.org/demo.aspx?prep=cv6p0010