Etazolate

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Etazolate
Etazolate.svg
Systematic (IUPAC) name
Ethyl 1-ethyl-4-[2-(propan-2-ylidene)hydrazinyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number 51022-77-6
ATC code None
PubChem CID 3277
ChemSpider 3162
UNII I89Y79062L YesY
ChEMBL CHEMBL356388
Chemical data
Formula C14H19N5O2 
Mol. mass 289.33 g/mol

Etazolate (SQ-20,009, EHT-0202) is an anxiolytic drug which is a pyrazolopyridine derivative and has unique pharmacological properties.[1][2][3] It acts as a positive allosteric modulator of the GABAA receptor at the barbiturate binding site,[4][5][6][7] as an adenosine antagonist of the A1 and A2 subtypes,[8] and as a phosphodiesterase inhibitor selective for the PDE4 isoform.[9][10][11] It is currently in clinical trials for the treatment of Alzheimer's disease.[12]

Synthesis[edit]

Cartazolate and Etazolate synthesis: E.R. SQUIBB & SONS, INC., NEW YORK, N.Y., US. DE 2123318 

See also[edit]

References[edit]

  1. ^ Hall, Judith A.; Morton, Ian (1999). Concise dictionary of pharmacological agents: properties and synonyms. Kluwer Academic. ISBN 0-7514-0499-3. 
  2. ^ Williams M (May 1983). "Anxioselective anxiolytics". Journal of Medicinal Chemistry 26 (5): 619–28. doi:10.1021/jm00359a001. PMID 6132997. 
  3. ^ Williams M, Risley EA (February 1979). "Enhancement of the binding of 3H-diazepam to rat brain membranes in vitro by SQ 20009, A novel anxiolytic, gamma-aminobutyric acid (GABA) and muscimol". Life Sciences 24 (9): 833–41. doi:10.1016/0024-3205(79)90367-9. PMID 449623. 
  4. ^ Zezula J, Slany A, Sieghart W (April 1996). "Interaction of allosteric ligands with GABAA receptors containing one, two, or three different subunits". European Journal of Pharmacology 301 (1–3): 207–14. doi:10.1016/0014-2999(96)00066-0. PMID 8773466. 
  5. ^ Remington, Gary; Baskys, Andrius (1996). Brain mechanisms and psychotropic drugs. Boca Raton: CRC Press. ISBN 0-8493-8386-2. 
  6. ^ M. Mishina; Kurachi, Yoshihisa (2000). Pharmacology of ionic channel function: activators and inhibitors. Berlin: Springer. ISBN 3-540-66127-1. 
  7. ^ Progress in Drug Research / Volume 31 (Progress in Drug Research). Boston: Birkhauser. 1987. p. 526. ISBN 3-7643-1837-6. 
  8. ^ Williams M, Jarvis MF (February 1988). "Adenosine antagonists as potential therapeutic agents". Pharmacology, Biochemistry, and Behavior 29 (2): 433–41. doi:10.1016/0091-3057(88)90182-7. PMID 3283781. 
  9. ^ Chasin M, Harris DN, Phillips MB, Hess SM (September 1972). "1-Ethyl-4-(isopropylidenehydrazino)-1H-pyrazolo-(3,4-b)-pyridine-5-carboxylic acid, ethyl ester, hydrochloride (SQ 20009)--a potent new inhibitor of cyclic 3',5'-nucleotide phosphodiesterases". Biochemical Pharmacology 21 (18): 2443–50. doi:10.1016/0006-2952(72)90414-5. PMID 4345859. 
  10. ^ Wang P, Myers JG, Wu P, Cheewatrakoolpong B, Egan RW, Billah MM (May 1997). "Expression, purification, and characterization of human cAMP-specific phosphodiesterase (PDE4) subtypes A, B, C, and D". Biochemical and Biophysical Research Communications 234 (2): 320–4. doi:10.1006/bbrc.1997.6636. PMID 9177268. 
  11. ^ Gresele, Paolo; Gresele, P. (2002). Platelets in thrombotic and non-thrombotic disorders: pathophysiology, pharmacology and therapeutics. Cambridge, UK: Cambridge University Press. ISBN 0-521-80261-X. 
  12. ^ "Pipeline | ExonHit". Retrieved August 2010.