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Cartazolate

Chemical compound

Not to be confused with tracazolate.

Pharmaceutical compound

Cartazolate
Clinical data

Routes of administration	By mouth
ATC code	None
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name Ethyl 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.

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Baclofen Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol, atenolol, betaxolol, nadolol, oxprenolol, pindolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Methallatal Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon AXS-17 (BAER-101, AZD-7325) CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

v
t
e

Purine receptor modulators

Receptor
(ligands)

P0 (adenine)

Agonists: 8-Aminoadenine
Adenine

P1
(adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine
2-Cl-IB-MECA
2-Chloroadenosine
2'-MeCCPA
4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
5'-N-ethylcarboxamidoadenosine
Adenosine
ADP
AMP
Apadenoson
ATL-146e
ATP
BAY 60–6583
Binodenoson
Capadenoson
CGS-21680
CP-532,903
CV-1808
Evodenoson
GR 79236
HENECA
LUF-5835
LUF-5845
N⁶-Cyclopentyladenosine
Namodenoson
NECA
Neladenoson dalanate
Piclidenoson
Regadenoson
SDZ WAG 994
Selodenoson
Sonedenoson
Tecadenoson
Trabodenoson
UK-432,097
YZG-331

Antagonists: 3-Chlorostyrylcaffeine (CSC)
7-Methylxanthine
8-Chlorotheophylline
8-Phenyl-1,3-dipropylxanthine
8-Phenyltheophylline
Acefylline
Aminophylline
ATL-444
AZD-4635
Bamifylline
Cafedrine
Caffeine
Caffeine citrate
Cartazolate
CGH-2466
CGS-15943
Choline theophyllinate
Ciforadenant
CPX
CVT-6883
Dimethazan
DMPX
DPCPX
Dyphylline
Enprofylline
Etazolate
Etrumadenant
Fenethylline
IBMX
Imaradenant
Inupadenant
ISAM-140
ISAM-R316
Isovaleric acid
Istradefylline
KF-26777
Lu AA41063
Lu AA47070
MRE3008F20
MRS-1191
MRS-1220
MRS-1334
MRS-1523
MRS-1706
MRS-1754
MRS-3777
MSX-2
MSX-3
MSX-4
Muvadenant
Paraxanthine
Pentoxifylline
Preladenant
Propentofylline
Proxyphylline
PSB-10
PSB-11
PSB-36
PSB-603
PSB-788
PSB-1115
PSB-1901
Reversine
Rolofylline
SCH-442,416
SCH-58261
Sipagladenant
Taminadenant
Theacrine
Theobromine
Theodrenaline
Theophylline
Tozadenant
Tracazolate
Vipadenant
VUF-5574
ZM-241,385

P2
(nucleotide)

P2X
(ATPTooltip Adenosine triphosphate)

Agonists: 2-Me-SATP
α,β-Me-ATP
Adenosine
ADP
AMP
Ap4A
Ap5A
ATP
ATPγS
BzATP
Cibacron blue
CTP
D-β,γ-Me-ATP
GTP
HT-AMP
Ivermectin
L-β,γ-Me-ATP
MRS-2219
PAPET-ATP
UTP
Zinc

Antagonists: 5-BDBD
A-317491
A-438079
A-740003
A-804598
A-839977
AF-353
AZ-10606120
AZ-11645373
BBG
Calcium
Calmidazolium
Chelerythrine
Copper
Emodin (Rheum officinale)
Evans blue
Gefapixant
GW-791343
HMA
Ip5I
isoPPADS
JNJ-47965567
KN-04
KN-62
Magnesium
MRS-2159
NF-023
NF-110
NF-157
NF-279
NF-449
Opiranserin (VVZ-149)
Oxidized-ATP
Phenol Red
Phenolphthalein
PPADS
PPNDS
PSB-12062
Puerarin (Radix puerariae)
Purotoxin 1
RB-2
Ro 0437626
Ro 51
RO-3
Sodium ferulate (Angelica sinensis, Ligusticum wallichii)
Suramin
TC-P 262
Tetramethylpyrazine (ligustrazine) (Ligusticum wallichii)
TNP-ATP
Zinc

P2Y

Agonists: 2-Me-SADP
2-Me-SATP
2-Thio-UTP
5-Br-UDP
5-OMe-UDP
α,β-Me-ATP
Adenosine
ADP
ADPβS
Ap3A
AR-C 67085MX
ATP
ATPγS
CTP
dATP
Denufosol
Diquafosol
IDP
ITP
INS-365
INS-37217
MRS-2365
MRS-2690
MRS-2693
MRS-2768
MRS-2957
MRS-4062
NF-546
PAPET-ATP
PSB-0474
PSB-1114
UDP
UDPβS
UDP-galactose
UDP-glucose
UDP-N-acetylglucosamine
Up3U
UTP
UTPγS

Antagonists: 2-Me-SAMP
A3P5PS
AMPαS
Ap4A
AR-C 66096
AR-C 67085MX
AR-C 69931MX
AR-C 118925XX
ATP
BzATP
C1330-7
Cangrelor
Clopidogrel
Elinogrel
Ip5I
MRS-2179
MRS-2211
MRS-2279
MRS-2395
MRS-2500
MRS-2578
NF-157
NF-340
PIT
PPADS
Prasugrel
PSB-0739
RB-2
Regrelor
Suramin
Ticagrelor
Ticlopidine
UDP

Transporter
(blockers)

CNTsTooltip Concentrative nucleoside transporters	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone
ENTsTooltip Equilibrative nucleoside transporters	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline
PMATTooltip Plasma membrane monoamine transporter	Decynium-22

Enzyme
(inhibitors)

XOTooltip Xanthine oxidase	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat
Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Precursors: Adenine
Adenosine
AMP
ADP
ATP
Cytosine
Cytidine
CMP
CDP
CTP
Guanine
Guanosine
GMP
GDP
GTP
Hypoxanthine
Inosine
IMP
IDP
ITP
Ribose
Uracil
Uridine
UMP
UDP
UTP

Others: Chrysophanol (rhubarb)

See also: Receptor/signaling modulators

v t e Phosphodiesterase inhibitors
PDE1	MMPX SCH-51866 Vinpocetine
PDE2	BAY 60-7550 Carbazeran EHNA Oxindole PDP
PDE3	Adibendan Amrinone (inamrinone) Anagrelide Benafentrine Bucladesine Carbazeran Cilostamide Cilostazol Enoximone Ensifentrine Imazodan KMUP-1 Meribendan Milrinone Olprinone Parogrelil Pimobendan Pumafentrine Quazinone RPL-554 Siguazodan Trequinsin Vesnarinone Zardaverine
PDE4	Apremilast Arofylline Atizoram Benafentrine Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline Crisaborole Denbutylline Difamilast Drotaverine Ensifentrine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Lotamilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Pumafentrine Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 Tetomilast Tofimilast YM-976 Zardaverine
PDE5	Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Norcarbodenafil SCH-51866 Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil
PDE7	BRL-50481
PDE9	BAY 73-6691 PF-04447943 Paraxanthine
PDE10	Balipodect Mardepodect MK-8189 Papaverine TC-E 5005 Tofisopam
PDE11	BC11-38
Non-selective	Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Pentoxifylline Propentofylline Theobromine Theophylline Zaprinast
Unsorted	Diazepam Diprophylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Pentifylline Proxyphylline Quercetin Satigrel Tolafentrine Trapidil
See also: Receptor/signaling modulators

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