en Cartazolate

Cartazolate
Clinical data
Routes of; administration	By mouth
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name Уthyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate;
CAS Number	34966-41-1;
PubChem CID	37015;
ChemSpider	33966;
UNII	8K93Z46WPY;
ChEMBL	ChEMBL8184;
CompTox Dashboard (EPA)	DTXSID20188511 ;
Chemical and physical data
Formula	C15H22N4O2
Molar mass	290.367 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(C1=CN=C(N(CC)N=C2)C2=C1NCCCC)OCC;

Cartazolate (SQ-65,396) is a drug of the pyrazolopyridine class. It acts as a GABA_A 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]

References

^ 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. doi:10.1016/0014-2999(80)90281-2. PMID 6103810.
^ 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. doi:10.1016/0014-2999(81)90213-2. PMID 6114867.
^ 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. doi:10.1523/JNEUROSCI.01-05-00471.1981. PMC 6564167. PMID 7050308.
^ 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. doi:10.1111/j.1471-4159.1990.tb02315.x. PMID 2154549. S2CID 25784613.
^ 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". Biochemical Pharmacology. 37 (4): 655–64. doi:10.1016/0006-2952(88)90139-6. PMC 3445624. PMID 2829919.
^ 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. doi:10.1007/BF00432761. PMID 6182575. S2CID 10122417.
^ O'Brien, Robert (1986). Receptor binding in drug research. New York: Dekker. p. 519. ISBN 0-8247-7548-1.
^ US 3966746, Hoehn, Hans & Denzel, Theodor, "Amino derivatives of pyrazolopyridine carboxamides", published 1976-06-29, assigned to Squibb & Sons Inc.

[pmid6103810-1] 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. doi:10.1016/0014-2999(80)90281-2. PMID 6103810.

[pmid6114867-2] 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. doi:10.1016/0014-2999(81)90213-2. PMID 6114867.

[pmid7050308-3] 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. doi:10.1523/JNEUROSCI.01-05-00471.1981. PMC 6564167. PMID 7050308.

[pmid2154549-4] 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. doi:10.1111/j.1471-4159.1990.tb02315.x. PMID 2154549. S2CID 25784613.

[pmid2829919-5] 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". Biochemical Pharmacology. 37 (4): 655–64. doi:10.1016/0006-2952(88)90139-6. PMC 3445624. PMID 2829919.

[pmid6182575-6] 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. doi:10.1007/BF00432761. PMID 6182575. S2CID 10122417.

[isbn0-8247-7548-1-7] O'Brien, Robert (1986). Receptor binding in drug research. New York: Dekker. p. 519. ISBN 0-8247-7548-1.

[8] US 3966746, Hoehn, Hans & Denzel, Theodor, "Amino derivatives of pyrazolopyridine carboxamides", published 1976-06-29, assigned to Squibb & Sons Inc.

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Cartazolate

See also

References

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