Wikipedia

ZK-93423

ZK-93423 is an anxiolytic drug from the β-Carboline family, closely related to abecarnil.[1] It is a nonbenzodiazepine GABAA agonist which is not subtype selective and stimulates α1, α2, α3, and α5-subunit containing GABAA receptors equally.[2] It has anticonvulsant, muscle relaxant and appetite stimulating properties comparable to benzodiazepine drugs.[3][4][5][6] 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 GABAA receptor.[7][8][9][10][11][12]

ZK-93423
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
  • ethyl 4-(methoxymethyl)-6-(phenylmethoxy) -9H-pyrido[5,4-b]indole-3-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H22N2O4
Molar mass390.439 g·mol−1
3D model (JSmol)
  • c3ccccc3COc(cc4)cc2c4[nH]c(cnc1C(=O)OCC)c2c1COC
  • InChI=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
  • Key:ALBKMJDFBZVHAK-UHFFFAOYSA-N
 ☒NcheckY (what is this?)  (verify)

See also

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References

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  1. ^ Zhang H, Larock RC (December 2002). "Synthesis of beta- and gamma-carbolines by the palladium-catalyzed iminoannulation of alkynes". The Journal of Organic Chemistry. 67 (26): 9318–30. doi:10.1021/jo026317u. PMID 12492334.9318-30&rft.date=2002-12&rft_id=info:doi/10.1021/jo026317u&rft_id=info:pmid/12492334&rft.aulast=Zhang&rft.aufirst=H&rft.au=Larock, RC&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  2. ^ Stephens DN, Shearman GT, Kehr W (1984). "Discriminative stimulus properties of beta-carbolines characterized as agonists and inverse agonists at central benzodiazepine receptors". Psychopharmacology. 83 (3): 233–9. doi:10.1007/BF00464787. PMID 6089245. S2CID 1479932.233-9&rft.date=1984&rft_id=https://api.semanticscholar.org/CorpusID:1479932#id-name=S2CID&rft_id=info:pmid/6089245&rft_id=info:doi/10.1007/BF00464787&rft.aulast=Stephens&rft.aufirst=DN&rft.au=Shearman, GT&rft.au=Kehr, W&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  3. ^ Klockgether T, Pardowitz I, Schwarz M, Sontag KH, Turski L (October 1985). "Evaluation of the muscle relaxant properties of a novel beta-carboline, ZK 93423 in rats and cats". British Journal of Pharmacology. 86 (2): 357–66. doi:10.1111/j.1476-5381.1985.tb08904.x. PMC 1916712. PMID 3931731.357-66&rft.date=1985-10&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1916712#id-name=PMC&rft_id=info:pmid/3931731&rft_id=info:doi/10.1111/j.1476-5381.1985.tb08904.x&rft.aulast=Klockgether&rft.aufirst=T&rft.au=Pardowitz, I&rft.au=Schwarz, M&rft.au=Sontag, KH&rft.au=Turski, L&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1916712&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  4. ^ Cooper SJ (January 1986). "Hyperphagic and anorectic effects of beta-carbolines in a palatable food consumption test: comparisons with triazolam and quazepam". European Journal of Pharmacology. 120 (3): 257–65. doi:10.1016/0014-2999(86)90466-8. PMID 3753939.257-65&rft.date=1986-01&rft_id=info:doi/10.1016/0014-2999(86)90466-8&rft_id=info:pmid/3753939&rft.au=Cooper SJ&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  5. ^ File SE, Baldwin HA (September 1987). "Effects of beta-carbolines in animal models of anxiety". Brain Research Bulletin. 19 (3): 293–9. doi:10.1016/0361-9230(87)90097-9. PMID 3315125. S2CID 54428766.293-9&rft.date=1987-09&rft_id=https://api.semanticscholar.org/CorpusID:54428766#id-name=S2CID&rft_id=info:pmid/3315125&rft_id=info:doi/10.1016/0361-9230(87)90097-9&rft.aulast=File&rft.aufirst=SE&rft.au=Baldwin, HA&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  6. ^ Löscher W, Hönack D, Hashem A (November 1987). "Anticonvulsant efficacy of clonazepam and the beta-carboline ZK 93423 during chronic treatment in amygdala-kindled rats". European Journal of Pharmacology. 143 (3): 403–14. doi:10.1016/0014-2999(87)90464-X. PMID 3691663.403-14&rft.date=1987-11&rft_id=info:doi/10.1016/0014-2999(87)90464-X&rft_id=info:pmid/3691663&rft.aulast=Löscher&rft.aufirst=W&rft.au=Hönack, D&rft.au=Hashem, A&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  7. ^ Dodd RH, Ouannès C, Potier MC, Prado de Carvalho L, Rossier J, Potier P (July 1987). "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 of Medicinal Chemistry. 30 (7): 1248–54. doi:10.1021/jm00390a023. PMID 3037081.1248-54&rft.date=1987-07&rft_id=info:doi/10.1021/jm00390a023&rft_id=info:pmid/3037081&rft.aulast=Dodd&rft.aufirst=RH&rft.au=Ouannès, C&rft.au=Potier, MC&rft.au=Prado de Carvalho, L&rft.au=Rossier, J&rft.au=Potier, P&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  8. ^ Hollinshead SP, Trudell ML, Skolnick P, Cook JM (March 1990). "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 of Medicinal Chemistry. 33 (3): 1062–9. doi:10.1021/jm00165a028. PMID 1968513.1062-9&rft.date=1990-03&rft_id=info:doi/10.1021/jm00165a028&rft_id=info:pmid/1968513&rft.aulast=Hollinshead&rft.aufirst=SP&rft.au=Trudell, ML&rft.au=Skolnick, P&rft.au=Cook, JM&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  9. ^ Diaz-Arauzo H, Evoniuk GE, Skolnick P, Cook JM (May 1991). "The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic". Journal of Medicinal Chemistry. 34 (5): 1754–6. doi:10.1021/jm00109a035. PMID 1674542.1754-6&rft.date=1991-05&rft_id=info:doi/10.1021/jm00109a035&rft_id=info:pmid/1674542&rft.aulast=Diaz-Arauzo&rft.aufirst=H&rft.au=Evoniuk, GE&rft.au=Skolnick, P&rft.au=Cook, JM&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  10. ^ Sharma RC, Ojha TN, Tiwari S, Singh P (1992). "Quantitative structure-activity relationship study of some benzodiazepine-receptor ligands having inverse agonist/antagonist and agonist actions". Drug Design and Discovery. 9 (2): 135–43. PMID 1338366.135-43&rft.date=1992&rft_id=info:pmid/1338366&rft.aulast=Sharma&rft.aufirst=RC&rft.au=Ojha, TN&rft.au=Tiwari, S&rft.au=Singh, P&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  11. ^ Cox ED, Diaz-Arauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM (July 1998). "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 of Medicinal Chemistry. 41 (14): 2537–52. doi:10.1021/jm970460b. PMID 9651158.2537-52&rft.date=1998-07&rft_id=info:doi/10.1021/jm970460b&rft_id=info:pmid/9651158&rft.aulast=Cox&rft.aufirst=ED&rft.au=Diaz-Arauzo, H&rft.au=Huang, Q&rft.au=Reddy, MS&rft.au=Ma, C&rft.au=Harris, B&rft.au=McKernan, R&rft.au=Skolnick, P&rft.au=Cook, JM&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
  12. ^ Ferretti V, Gilli P, Borea PA (August 2004). "Structural features controlling the binding of beta-carbolines to the benzodiazepine receptor". Acta Crystallographica B. 60 (Pt 4): 481–9. doi:10.1107/S0108768104013564. PMID 15258407.481-9&rft.date=2004-08&rft_id=info:doi/10.1107/S0108768104013564&rft_id=info:pmid/15258407&rft.aulast=Ferretti&rft.aufirst=V&rft.au=Gilli, P&rft.au=Borea, PA&rfr_id=info:sid/en.wikipedia.org:ZK-93423" class="Z3988">
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