Etazolate

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 GABA_A 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]

Routes of
administrationOral

ATC code

none

Legal status

In general: uncontrolled

CAS Number

51022-77-6

Quick facts Clinical data, Routes ofadministration ...

Etazolate
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name Ethyl 1-ethyl-4-[2-(propan-2-ylidene)hydrazinyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
CAS Number	51022-77-6
PubChem CID	3277
IUPHAR/BPS	7336
ChemSpider	3162
UNII	I89Y79062L
ChEBI	CHEBI:138502
ChEMBL	ChEMBL356388
CompTox Dashboard (EPA)	DTXSID4048434
Chemical and physical data
Formula	C₁₄H₁₉N₅O₂
Molar mass	289.339 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN1C2=NC=C(C(=C2C=N1)NN=C(C)C)C(=O)OCC
InChI InChI=1S/C14H19N5O2/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2/h7-8H,5-6H2,1-4H3,(H,15,18) Key:OPQRBXUBWHDHPQ-UHFFFAOYSA-N

References

[1]
Hall JA, Morton I (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): 619–628. 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): 833–841. 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): 207–214. doi:10.1016/0014-2999(96)00066-0. PMID 8773466.
[5]
Davies MF (1996). "The Pharmacology of the Gamma-Aminobutyric Acid System". In Remington G, Baskys A (eds.). Brain mechanisms and psychotropic drugs. Boca Raton: CRC Press. ISBN 0-8493-8386-2.
[6]
Olsen RW, Gordey M (2000). "GABAA Receptor Chloride Ion Channels". In Mishina M, Kurachi Y (eds.). Pharmacology of ionic channel function: activators and inhibitors. Handbook of Experimental Pharmacology. Vol. 147. Berlin: Springer. pp. 499–517. doi:10.1007/978-3-642-57083-4_19. ISBN 3-540-66127-1.
[7]
Olsen RW (1987). "GABA-Drug Interactions". In Jucker E (ed.). Progress in Drug Research. Vol. 31. Boston: Birkhauser. 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): 433–441. doi:10.1016/0091-3057(88)90182-7. PMID 3283781. S2CID 35635747.
[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): 2443–2450. 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): 320–324. Bibcode:1997BBRC..234..320W. doi:10.1006/bbrc.1997.6636. PMID 9177268.
[11]
Daniel JL (2002). "Platelet signalling; cAMP and cGMP". In Gresele P (ed.). Platelets in thrombotic and non-thrombotic disorders: pathophysiology, pharmacology and therapeutics. Cambridge, UK: Cambridge University Press. ISBN 0-521-80261-X.
[12]
"EHT 0202". Pipeline. ExonHit. Archived from the original on 2011-01-11.

See also

References

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