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Revision as of 22:19, 18 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Misplaced Pages← Previous edit Latest revision as of 16:39, 24 January 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers170,149 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 376419235 | verifiedrevid = 451222547
| IUPAC_name = ethyl 4-(methoxymethyl)-6-(phenylmethoxy) -9H-pyridoindole-3-carboxylate | IUPAC_name = ethyl 4-(methoxymethyl)-6-(phenylmethoxy) -9H-pyridoindole-3-carboxylate
| image = ZK-93423_structure.png | image = ZK-93423_structure.png
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<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 4346
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 83910-44-5 | CAS_number = 83910-44-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B6PWX5B47Q
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID = 108771
| ChEBI = 92593
| ChEMBL = 1518572


<!--Chemical data--> <!--Chemical data-->
| C=23 | H=22 | N=2 | O=4 | C=23 | H=22 | N=2 | O=4
| smiles = c3ccccc3COc(cc4)cc2c4c(cnc1C(=O)OCC)c2c1COC
| molecular_weight = 390.431 g/mol
| StdInChI = 1S/C23H22N2O4/c1-3-28-23(26)22-18(14-27-2)21-17-11-16(29-13-15-7-5-4-6-8-15)9-10-19(17)25-20(21)12-24-22/h4-12,25H,3,13-14H2,1-2H3
| smiles = c3ccccc3COc(cc4)cc2c4nc(cnc1C(=O)OCC)c2c1COC
| StdInChIKey = ALBKMJDFBZVHAK-UHFFFAOYSA-N
}} }}


'''ZK-93423''' is an ] drug from the ] family, closely related to ].<ref name="pmid12492334">{{cite journal |author=Zhang H, Larock RC |title=Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes |journal=The Journal of Organic Chemistry |volume=67 |issue=26 |pages=9318–30 |year=2002 |month=December |pmid=12492334 |doi= 10.1021/jo026317u|url=}}</ref> It is a ] ] ] which is not subtype selective and stimulates α<sub>1</sub>, α<sub>2</sub>, α<sub>3</sub>, and α<sub>5</sub>-subunit containing GABA<sub>A</sub> receptors equally.<ref name="pmid6089245">{{cite journal |author=Stephens DN, Shearman GT, Kehr W |title=Discriminative stimulus properties of beta-carbolines characterized as agonists and inverse agonists at central benzodiazepine receptors |journal=Psychopharmacology |volume=83 |issue=3 |pages=233–9 |year=1984 |pmid=6089245 |doi= 10.1007/BF00464787|url=}}</ref> It has ], ] and appetite stimulating properties comparable to ] drugs.<ref name="pmid3931731">{{cite journal |author=Klockgether T, Pardowitz I, Schwarz M, Sontag KH, Turski L |title=Evaluation of the muscle relaxant properties of a novel beta-carboline, ZK 93423 in rats and cats |journal=British Journal of Pharmacology |volume=86 |issue=2 |pages=357–66 |year=1985 |month=October |pmid=3931731 |pmc=1916712 |doi= |url=}}</ref><ref name="pmid3753939">{{cite journal |author=Cooper SJ |title=Hyperphagic and anorectic effects of beta-carbolines in a palatable food consumption test: comparisons with triazolam and quazepam |journal=European Journal of Pharmacology |volume=120 |issue=3 |pages=257–65 |year=1986 |month=January |pmid=3753939 |doi= 10.1016/0014-2999(86)90466-8|url=}}</ref><ref name="pmid3315125">{{cite journal |author=File SE, Baldwin HA |title=Effects of beta-carbolines in animal models of anxiety |journal=Brain Research Bulletin |volume=19 |issue=3 |pages=293–9 |year=1987 |month=September |pmid=3315125 |doi= 10.1016/0361-9230(87)90097-9|url=}}</ref><ref name="pmid3691663">{{cite journal |author=Löscher W, Hönack D, Hashem A |title=Anticonvulsant efficacy of clonazepam and the beta-carboline ZK 93423 during chronic treatment in amygdala-kindled rats |journal=European Journal of Pharmacology |volume=143 |issue=3 |pages=403–14 |year=1987 |month=November |pmid=3691663 |doi= 10.1016/0014-2999(87)90464-X|url=}}</ref> ZK-93423 has also been used as a base to develop new and improved beta-carboline derivatives and help map the binding site of the GABA<sub>A</sub> receptor.<ref name="pmid3037081">{{cite journal |author=Dodd RH, Ouannès C, Potier MC, Prado de Carvalho L, Rossier J, Potier P |title=Synthesis of beta-carboline-benzodiazepine hybrid molecules: use of the known structural requirements for benzodiazepine and beta-carboline binding in designing a novel, high-affinity ligand for the benzodiazepine receptor |journal=Journal of Medicinal Chemistry |volume=30 |issue=7 |pages=1248–54 |year=1987 |month=July |pmid=3037081 |doi= 10.1021/jm00390a023|url=}}</ref><ref name="pmid1968513">{{cite journal |author=Hollinshead SP, Trudell ML, Skolnick P, Cook JM |title=Structural requirements for agonist actions at the benzodiazepine receptor: studies with analogues of 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester |journal=Journal of Medicinal Chemistry |volume=33 |issue=3 |pages=1062–9 |year=1990 |month=March |pmid=1968513 |doi= 10.1021/jm00165a028|url=}}</ref><ref name="pmid1674542">{{cite journal |author=Diaz-Arauzo H, Evoniuk GE, Skolnick P, Cook JM |title=The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic |journal=Journal of Medicinal Chemistry |volume=34 |issue=5 |pages=1754–6 |year=1991 |month=May |pmid=1674542 |doi= 10.1021/jm00109a035|url=}}</ref><ref name="pmid1338366">{{cite journal |author=Sharma RC, Ojha TN, Tiwari S, Singh P |title=Quantitative structure-activity relationship study of some benzodiazepine-receptor ligands having inverse agonist/antagonist and agonist actions |journal=Drug Design and Discovery |volume=9 |issue=2 |pages=135–43 |year=1992 |pmid=1338366 |doi= |url=}}</ref><ref name="pmid9651158">{{cite journal |author=Cox ED, Diaz-Arauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM |title=Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors |journal=Journal of Medicinal Chemistry |volume=41 |issue=14 |pages=2537–52 |year=1998 |month=July |pmid=9651158 |doi=10.1021/jm970460b |url=}}</ref><ref name="pmid15258407">{{cite journal |author=Ferretti V, Gilli P, Borea PA |title=Structural features controlling the binding of beta-carbolines to the benzodiazepine receptor |journal=Acta Crystallographica B |volume=60 |issue=Pt 4 |pages=481–9 |year=2004 |month=August |pmid=15258407 |doi=10.1107/S0108768104013564 |url=}}</ref> '''ZK-93423''' is an ] drug from the ] family, closely related to ].<ref name="pmid12492334">{{cite journal |vauthors=Zhang H, Larock RC |title=Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes |journal=The Journal of Organic Chemistry |volume=67 |issue=26 |pages=9318–30 |date=December 2002 |pmid=12492334 |doi= 10.1021/jo026317u}}</ref> It is a ] ] ] which is not subtype selective and stimulates α<sub>1</sub>, α<sub>2</sub>, α<sub>3</sub>, and α<sub>5</sub>-subunit containing GABA<sub>A</sub> receptors equally.<ref name="pmid6089245">{{cite journal |vauthors=Stephens DN, Shearman GT, Kehr W |title=Discriminative stimulus properties of beta-carbolines characterized as agonists and inverse agonists at central benzodiazepine receptors |journal=Psychopharmacology |volume=83 |issue=3 |pages=233–9 |year=1984 |pmid=6089245 |doi= 10.1007/BF00464787|s2cid=1479932 }}</ref> It has ], ] and appetite stimulating properties comparable to ] drugs.<ref name="pmid3931731">{{cite journal |vauthors=Klockgether T, Pardowitz I, Schwarz M, Sontag KH, Turski L |title=Evaluation of the muscle relaxant properties of a novel beta-carboline, ZK 93423 in rats and cats |journal=] |volume=86 |issue=2 |pages=357–66 |date=October 1985 |pmid=3931731 |pmc=1916712 |doi= 10.1111/j.1476-5381.1985.tb08904.x}}</ref><ref name="pmid3753939">{{cite journal |author=Cooper SJ |title=Hyperphagic and anorectic effects of beta-carbolines in a palatable food consumption test: comparisons with triazolam and quazepam |journal=European Journal of Pharmacology |volume=120 |issue=3 |pages=257–65 |date=January 1986 |pmid=3753939 |doi= 10.1016/0014-2999(86)90466-8}}</ref><ref name="pmid3315125">{{cite journal |vauthors=File SE, Baldwin HA |title=Effects of beta-carbolines in animal models of anxiety |journal=Brain Research Bulletin |volume=19 |issue=3 |pages=293–9 |date=September 1987 |pmid=3315125 |doi= 10.1016/0361-9230(87)90097-9|s2cid=54428766 }}</ref><ref name="pmid3691663">{{cite journal |vauthors=Löscher W, Hönack D, Hashem A |title=Anticonvulsant efficacy of clonazepam and the beta-carboline ZK 93423 during chronic treatment in amygdala-kindled rats |journal=European Journal of Pharmacology |volume=143 |issue=3 |pages=403–14 |date=November 1987 |pmid=3691663 |doi= 10.1016/0014-2999(87)90464-X}}</ref> ZK-93423 has also been used as a base to develop new and improved beta-carboline derivatives and help map the binding site of the GABA<sub>A</sub> receptor.<ref name="pmid3037081">{{cite journal |vauthors=Dodd RH, Ouannès C, Potier MC, Prado de Carvalho L, Rossier J, Potier P |title=Synthesis of beta-carboline-benzodiazepine hybrid molecules: use of the known structural requirements for benzodiazepine and beta-carboline binding in designing a novel, high-affinity ligand for the benzodiazepine receptor |journal=Journal of Medicinal Chemistry |volume=30 |issue=7 |pages=1248–54 |date=July 1987 |pmid=3037081 |doi= 10.1021/jm00390a023}}</ref><ref name="pmid1968513">{{cite journal |vauthors=Hollinshead SP, Trudell ML, Skolnick P, Cook JM |title=Structural requirements for agonist actions at the benzodiazepine receptor: studies with analogues of 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester |journal=Journal of Medicinal Chemistry |volume=33 |issue=3 |pages=1062–9 |date=March 1990 |pmid=1968513 |doi= 10.1021/jm00165a028}}</ref><ref name="pmid1674542">{{cite journal |vauthors=Diaz-Arauzo H, Evoniuk GE, Skolnick P, Cook JM |title=The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic |journal=Journal of Medicinal Chemistry |volume=34 |issue=5 |pages=1754–6 |date=May 1991 |pmid=1674542 |doi= 10.1021/jm00109a035}}</ref><ref name="pmid1338366">{{cite journal |vauthors=Sharma RC, Ojha TN, Tiwari S, Singh P |title=Quantitative structure-activity relationship study of some benzodiazepine-receptor ligands having inverse agonist/antagonist and agonist actions |journal=Drug Design and Discovery |volume=9 |issue=2 |pages=135–43 |year=1992 |pmid=1338366 }}</ref><ref name="pmid9651158">{{cite journal |vauthors=Cox ED, Diaz-Arauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM |title=Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors |journal=Journal of Medicinal Chemistry |volume=41 |issue=14 |pages=2537–52 |date=July 1998 |pmid=9651158 |doi=10.1021/jm970460b }}</ref><ref name="pmid15258407">{{cite journal |vauthors=Ferretti V, Gilli P, Borea PA |title=Structural features controlling the binding of beta-carbolines to the benzodiazepine receptor |journal=Acta Crystallographica B |volume=60 |issue=Pt 4 |pages=481–9 |date=August 2004 |pmid=15258407 |doi=10.1107/S0108768104013564 }}</ref>


==See also== ==See also==
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{{Anxiolytics}} {{Anxiolytics}}
{{GABAAR PAMs}}


{{DEFAULTSORT:Zk-93423}}
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{{DEFAULTSORT:Zk-93423}}