Cartazolate

Cartazolate

Systematic (IUPAC) name
ethyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	Oral
Identifiers
CAS number	34966-41-1
ATC code	None
PubChem	CID 37015
ChemSpider	33966
UNII	8K93Z46WPY^Y
Chemical data
Formula	C₁₅H₂₂N₄O₂
Mol. mass	290.36 g/mol
SMILES	eMolecules & PubChem

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]

References [link]

^ 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. https://linkinghub.elsevier.com/retrieve/pii/0014-2999(81)90213-2.
^ 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. PMID 7050308. https://www.jneurosci.org/cgi/pmidlookup?view=long&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. PMID 2154549.
^ 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. 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.
^ O'Brien, Robert (1986). Receptor binding in drug research. New York: Dekker. pp. 519. ISBN 0-8247-7548-1. https://books.google.com/books?id=GDE2VTeeHPIC&lpg=PA78&dq=cartazolate&pg=PA78#v=onepage&q&f=false.

Anxiolytics (N05B)

GABA_A PAMs

Benzodiazepine	Adinazolam Alprazolam Bretazenil Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam Ethyl Loflazepate Etizolam Fludiazepam Halazepam Imidazenil Ketazolam Lorazepam Medazepam Nordazepam Oxazepam Pinazepam Prazepam

Carbamates	Emylcamate Mebutamate Meprobamate (Carisoprodol, Tybamate) Phenprobamate Procymate

Nonbenzodiazepines	Abecarnil Adipiplon Alpidem CGS-8216 CGS-9896 CGS-13767 CGS-20625 Divaplon ELB-139 Fasiplon GBLD-345 Gedocarnil L-838,417 NS-2664 NS-2710 Ocinaplon Pagoclone Panadiplon Pipequaline RWJ-51204 SB-205,384 SL-651,498 Taniplon TP-003 TP-13 TPA-023 Y-23684 ZK-93423

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Others	Chlormezanone Ethanol (Alcohol) Etifoxine Kavalactones (Kava Kava) Skullcap Valerenic Acid (Valerian)

mGluR₂_/₃ Agonists

Eglumegad

mGluR5 NAMs

Fenobam

TSPO agonists

σ₁ agonists

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)

v t e GABA_A receptor PAMs

Barbiturates	Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Bucolome Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Prazitone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

Benzodiazepines	Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Chlordiazepoxide Ciclotizolam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Diazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Girisopam Halazepam Haloxazolam Iclazepam Imidazenil Ketazolam Lofendazam Lopirazepam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Nerisopam Nimetazepam Nitrazepam Nitrazepate Nordazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tofisopam Triazolam Triflubazam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates	Carisbamate Carisoprodol Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Methocarbamol Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem Necopidem Saripidem Zolpidem; Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon; Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 ELB-139 GBLD-345 L-838,417 NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Y-23684

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone

Volatiles/gases	2-Methyl-2-butanol Acetone Acetophenone Acetylglycinamide chloral hydrate Benzene Butane Butanol Butylene Centalun Chloral Chloral hydrate Chlorobutanol Chloroform Cyclopropane Desflurane Dichloromethane Diethyl ether Enflurane Ethanol (Alcohol) Ethyl chloride Ethylene Gasoline Halothane Isoflurane Kerosine Menthol Methanol Methoxyflurane Methoxypropane Methylbutanol Nitric oxide Nitrogen Nitrous oxide Paraldehyde Pentanol Propane Propanol Propylene Sevoflurane Toluene Trichloroethanol Trichloroethylene Vinyl ether Xenon

Others	Bromide (Lithium bromide Potassium bromide Sodium bromide) Chloralodol Chloralose Chlormezanone Clomethiazole DEABL Etazepine Ethchlorvynol Etifoxine Etomidate GABA Kavalactones (Kava) Loreclezole Methylpentynol Metomidate Org 25,435 Petrichloral Propanidid Skullcap Stiripentol Sulfonmethane Tetronal Triclofos Trional Valeric acid Valerenic acid (Valerian)

Adenosinergics

Receptor ligands

Agonists	2-(1-Hexynyl)-N-methyladenosine 2-Cl-IB-MECA 2'-MeCCPA 5'-N-ethylcarboxamidoadenosine ATL-146e BAY 60–6583 CCPA CGS-21680 CP-532,903 GR 79236 LUF-5835 LUF-5845 N⁶-Cyclopentyladenosine Regadenoson SDZ WAG 994 UK-432,097

Antagonists	8-Phenyl-1,3-dipropylxanthine Acefylline Aminophylline Bamifylline Caffeine CGS-15943 8-Chlorotheophylline CPX CVT-6883 Dimethazan DPCPX Fenethylline Istradefylline KF-26777 MRE3008F20 MRS-1220 MRS-1334 MRS-1706 MRS-1754 MRS-3777 Paraxanthine Pentoxifylline Preladenant Propentofylline PSB-10 PSB-11 PSB 36 PSB-603 PSB-788 PSB-1115 Rolofylline SCH-442,416 SCH-58261 Theobromine Theophylline VUF-5574 ZM-241,385

Reuptake inhibitors

Plasmalemmal

ENT inhibitors	Dilazep Dipyridamole Hexobendine Pentoxifylline Propentofylline Barbituates Ethanol Benzodiazepines

Vesicular

VNT inhibitors

v t e Phosphodiesterase inhibitors

PDE1	MMPX • SCH-51866 • Vinpocetine

PDE2	BAY 60-7550 • EHNA

PDE3	Amrinone • Anagrelide • Bucladesine • Cilostamide • Cilostazol • Enoximone • KMUP-1 • Milrinone • Quazinone • RPL-554 • Siguazodan • Trequinsin • Vesnarinone • Zardaverine

PDE4	Arofylline • Cilomilast • CP-80633 • Denbutylline • Drotaverine • Etazolate • Filaminast • Glaucine • HT-0712 • Ibudilast • ICI-63197 • Irsogladine • Luteolin • Mesembrine • Piclamilast • Roflumilast • Rolipram • Ro20-1724 • RPL-554 • YM-976

PDE5	Acetildenafil • Aildenafil • Avanafil • Dipyridamole • Icariin • Lodenafil • Mirodenafil • MY-5445 • Nitrosoprodenafil • Sildenafil • Sulfoaildenafil • T-0156 • Tadalafil • Udenafil • Vardenafil

PDE6	Zaprinast

PDE7	BRL-50481

PDE9	BAY 73-6691 • SCH-51866

PDE10	Papaverine • PF-2545920 • Tofisopam

Nonselective	Caffeine • Doxofylline • IBMX • Pentoxifylline • Propentofylline • Theophylline

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