:Cartazolate

{{Short description|Chemical compound}}

{{distinguish|tracazolate}}

{{Drugbox

| IUPAC_name = Уthyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

| image = Cartazolate.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = By mouth

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 34966-41-1

| ATC_prefix = None

| ATC_suffix =

| PubChem = 37015

| ChemSpiderID = 33966

| ChEMBL = 8184

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8K93Z46WPY

| C=15 | H=22 | N=4 | O=2

| 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.{{cite journal |vauthors=Placheta P, Karobath M | title = In vitro modulation by SQ 20009 and SQ 65396 of GABA receptor binding in rat CNS membranes | journal = European Journal of Pharmacology | volume = 62 | issue = 2–3 | pages = 225–8 |date=March 1980 | pmid = 6103810 | doi = 10.1016/0014-2999(80)90281-2}}{{cite journal |vauthors=Supavilai P, Karobath M | title = Action of pyrazolopyridines as modulators of [3H]flunitrazepam binding to the gaba/benzodiazepine receptor complex of the cerebellum | journal = European Journal of Pharmacology | volume = 70 | issue = 2 | pages = 183–93 |date=March 1981 | pmid = 6114867 | doi = 10.1016/0014-2999(81)90213-2}}{{cite journal |vauthors=Leeb-Lundberg F, Snowman A, Olsen RW | title = Perturbation of benzodiazepine receptor binding by pyrazolopyridines involves picrotoxinin/barbiturate receptor sites | journal = Journal of Neuroscience | volume = 1 | issue = 5 | pages = 471–7 |date=May 1981 | pmid = 7050308 | doi = 10.1523/JNEUROSCI.01-05-00471.1981| pmc = 6564167 | doi-access = free }}{{cite journal |vauthors=Bristow DR, Martin IL | title = Biochemical characterization of an isolated and functionally reconstituted gamma-aminobutyric acid/benzodiazepine receptor | journal = Journal of Neurochemistry | volume = 54 | issue = 3 | pages = 751–61 |date=March 1990 | pmid = 2154549 | doi = 10.1111/j.1471-4159.1990.tb02315.x| s2cid = 25784613 }} It is also known to act as an adenosine antagonist at the A₁ and A₂ subtypes and as a phosphodiesterase inhibitor.{{cite journal |vauthors=Daly JW, Hong O, Padgett WL, Shamim MT, Jacobson KA, Ukena D | title = Non-xanthine heterocycles: activity as antagonists of A1- and A2-adenosine receptors | journal = Biochemical Pharmacology | volume = 37 | issue = 4 | pages = 655–64 |date=February 1988 | pmid = 2829919 | doi = 10.1016/0006-2952(88)90139-6| pmc=3445624}}{{cite journal | author = Wachtel H | title = Characteristic behavioural alterations in rats induced by rolipram and other selective adenosine cyclic 3', 5'-monophosphate phosphodiesterase inhibitors | journal = Psychopharmacology | volume = 77 | issue = 4 | pages = 309–16 | year = 1982 | pmid = 6182575 | doi = 10.1007/BF00432761| s2cid = 10122417 }} Cartazolate was tested in human clinical trials and was found to be efficacious for anxiety but was never marketed.{{cite book | author = O'Brien, Robert | title = Receptor binding in drug research | publisher = Dekker | location = New York | year = 1986 | page = 519 | isbn = 0-8247-7548-1 | url = https://books.google.com/books?id=GDE2VTeeHPIC&q=cartazolate&pg=PA78}} It was developed by a team at E.R. Squibb and Sons in the 1970s.{{cite patent||country=US|number=3966746|pubdate=1976-06-29|title=Amino derivatives of pyrazolopyridine carboxamides|assign=Squibb & Sons Inc.|inventor1-last=Hoehn|inventor1-first=Hans|inventor2-last=Denzel|inventor2-first=Theodor}}