WAY-100135: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'CAS_number_Ref') per [[WP:CHEMVALID|Chem/Drugbox va...
No edit summary
Line 1: Line 1:
{{Drugbox
{{Drugbox
| verifiedrevid = 449588681
| verifiedrevid = 449588681
| IUPAC_name = (S)-N-tert-butyl- 3-(4-(2-methoxyphenyl)- piperazin-1-yl)- 2-phenylpropanamide
| IUPAC_name = (''S'')-''N''-''tert''-butyl-3-(4-(2-methoxyphenyl)-piperazin-1-yl)-2-phenylpropanamide
| image = WAY-100,135_structure.png
| image = WAY-100,135_structure.png
| width = 200
| width = 200
Line 17: Line 17:


<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=33 | N=3 | O=2
| C = 24 | H = 33 | N = 3 | O = 2
| molecular_weight = 395.536 g/mol
| molecular_weight = 395.536 g/mol
| smiles = c2ccccc2C(C(=O)NC(C)(C)C)CN(CC3)CCN3c1ccccc1OC
| smiles = c2ccccc2C(C(=O)NC(C)(C)C)CN(CC3)CCN3c1ccccc1OC
}}
}}


'''WAY-100,135''' is a [[piperazine]] [[drug]] and research chemical used in scientific studies. It was originally believed to act as a selective [[5-HT1A|5-HT<sub>1A</sub>]] [[receptor (biochemistry)|receptor]] [[antagonist]], but subsequent research demonstrated that it also acts as a [[partial agonist]] at the [[5-HT1B|5-HT<sub>1B</sub>]] and [[5-HT1D|5-HT<sub>1D</sub>]] receptors.<ref name="pmid8496920">{{cite journal | author = Cliffe IA, Brightwell CI, Fletcher A, Forster EA, Mansell HL, Reilly Y, Routledge C, White AC. | title = (S)-N-tert-butyl- 3-(4-(2-methoxyphenyl)- piperazin-1-yl)- 2-phenylpropanamide [(S)-WAY-100135]: a selective antagonist at presynaptic and postsynaptic 5-HT1A receptors. | journal = J Med Chem. | volume = 36 | issue = 10 | pages = 1509–1510 | year = 1993 | pmid = 8496920 | doi = 10.1021/jm00062a028 }}</ref><ref name="pmid9208142">{{cite journal | author = Davidson C, Ho M, Price GW, Jones BJ, Stamford JA. | title = (+)-WAY 100135, a partial agonist, at native and recombinant 5-HT1B/1D receptors | journal = Br J Pharmacol. | volume = 121 | issue = 4 | pages = 737–742 | year = 1997 | pmid = 9208142 | doi = 10.1038/sj.bjp.0701197 | pmc = 1564750 }}</ref>
'''WAY-100,135''' is a [[serotonergic]] [[drug]] of the [[phenylpiperazine]] family which is used in [[scientific research]].<ref name="pmid8365456">{{cite journal | author = Fletcher A, Bill DJ, Bill SJ, ''et al.'' | title = WAY100135: a novel, selective antagonist at presynaptic and postsynaptic 5-HT1A receptors | journal = European Journal of Pharmacology | volume = 237 | issue = 2-3 | pages = 283–91 | year = 1993 | month = June | pmid = 8365456 | doi = | url = }}</ref> It acts as [[potency (pharmacology)|potent]] [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] [[receptor antagonist|antagonist]],<ref name="pmid8496920">{{cite journal | author = Cliffe IA, Brightwell CI, Fletcher A, ''et al.'' | title = (S)-N-tert-butyl-3-(4-(2-methoxyphenyl)-piperazin-1-yl)-2-phenylpropanamide [(S)-WAY-100135]: a selective antagonist at presynaptic and postsynaptic 5-HT1A receptors | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 10 | pages = 1509–10 | year = 1993 | month = May | pmid = 8496920 | doi = | url = }}</ref> and was originally believed to be highly [[binding selectivity|selective]], but further studies have demonstrated that it also acts as a [[partial agonist]] of the [[5-HT1D|5-HT<sub>1D</sub>]] (pK<sub>i</sub> = 7.58; virtually the same affinity for 5-HT<sub>1A</sub>), and to a much lesser extent, [[5-HT1B|5-HT<sub>1B</sub> receptor]] (pK<sub>i</sub> = 5.82).<ref name="pmid9208142">{{cite journal | author = Davidson C, Ho M, Price GW, Jones BJ, Stamford JA | title = (+)-WAY 100135, a partial agonist, at native and recombinant 5-HT1B/1D receptors | journal = British Journal of Pharmacology | volume = 121 | issue = 4 | pages = 737–42 | year = 1997 | month = June | pmid = 9208142 | pmc = 1564750 | doi = 10.1038/sj.bjp.0701197 | url = http://dx.doi.org/10.1038/sj.bjp.0701197}}</ref> These findings may have prompted the development of the related compound [[WAY-100,635]], another purportedly selective and even more potent 5-HT<sub>1A</sub> antagonist, which was synthesized shortly thereafter.<ref name="pmid8768728">{{cite journal | author = Fornal CA, Metzler CW, Gallegos RA, Veasey SC, McCreary AC, Jacobs BL | title = WAY-100635, a potent and selective 5-hydroxytryptamine1A antagonist, increases serotonergic neuronal activity in behaving cats: comparison with (S)-WAY-100135 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 278 | issue = 2 | pages = 752–62 | year = 1996 | month = August | pmid = 8768728 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8768728}}</ref> However, WAY-100,635 turned out to be non-selective as well, acting additionally as a potent [[D4 receptor|D<sub>4</sub> receptor]] [[agonist]].<ref name="pmid16915381">{{cite journal | author = Chemel BR, Roth BL, Armbruster B, Watts VJ, Nichols DE | title = WAY-100635 is a potent dopamine D4 receptor agonist | journal = Psychopharmacology | volume = 188 | issue = 2 | pages = 244–51 | year = 2006 | month = October | pmid = 16915381 | doi = 10.1007/s00213-006-0490-4 | url = http://dx.doi.org/10.1007/s00213-006-0490-4}}</ref>


== See also ==
== See also ==
Line 28: Line 28:


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}



{{Serotonergics}}
{{Serotonergics}}
{{Piperazines}}
{{Piperazines}}

⚫
[[Category:Piperazines]]
[[Category:Phenol ethers]]
[[Category:5-HT1A antagonists]]
[[Category:Amides]]
[[Category:Amides]]
[[Category:Phenol ethers]]
⚫
[[Category:Piperazines]]




Revision as of 16:04, 14 May 2012

WAY-100135
Identifiers
  • (S)-N-tert-butyl-3-(4-(2-methoxyphenyl)-piperazin-1-yl)-2-phenylpropanamide
CAS Number
PubChem CID
IUPHAR/BPS
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H33N3O2
Molar mass395.536 g/mol g·mol−1
3D model (JSmol)
  • c2ccccc2C(C(=O)NC(C)(C)C)CN(CC3)CCN3c1ccccc1OC
  (verify)

WAY-100,135 is a serotonergic drug of the phenylpiperazine family which is used in scientific research.[1] It acts as potent 5-HT1A receptor antagonist,[2] and was originally believed to be highly selective, but further studies have demonstrated that it also acts as a partial agonist of the 5-HT1D (pKi = 7.58; virtually the same affinity for 5-HT1A), and to a much lesser extent, 5-HT1B receptor (pKi = 5.82).[3] These findings may have prompted the development of the related compound WAY-100,635, another purportedly selective and even more potent 5-HT1A antagonist, which was synthesized shortly thereafter.[4] However, WAY-100,635 turned out to be non-selective as well, acting additionally as a potent D4 receptor agonist.[5]

See also

References

  1. ^ Fletcher A, Bill DJ, Bill SJ; et al. (1993). "WAY100135: a novel, selective antagonist at presynaptic and postsynaptic 5-HT1A receptors". European Journal of Pharmacology. 237 (2–3): 283–91. PMID 8365456. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Cliffe IA, Brightwell CI, Fletcher A; et al. (1993). "(S)-N-tert-butyl-3-(4-(2-methoxyphenyl)-piperazin-1-yl)-2-phenylpropanamide [(S)-WAY-100135]: a selective antagonist at presynaptic and postsynaptic 5-HT1A receptors". Journal of Medicinal Chemistry. 36 (10): 1509–10. PMID 8496920. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Davidson C, Ho M, Price GW, Jones BJ, Stamford JA (1997). "(+)-WAY 100135, a partial agonist, at native and recombinant 5-HT1B/1D receptors". British Journal of Pharmacology. 121 (4): 737–42. doi:10.1038/sj.bjp.0701197. PMC 1564750. PMID 9208142. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Fornal CA, Metzler CW, Gallegos RA, Veasey SC, McCreary AC, Jacobs BL (1996). "WAY-100635, a potent and selective 5-hydroxytryptamine1A antagonist, increases serotonergic neuronal activity in behaving cats: comparison with (S)-WAY-100135". The Journal of Pharmacology and Experimental Therapeutics. 278 (2): 752–62. PMID 8768728. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Chemel BR, Roth BL, Armbruster B, Watts VJ, Nichols DE (2006). "WAY-100635 is a potent dopamine D4 receptor agonist". Psychopharmacology. 188 (2): 244–51. doi:10.1007/s00213-006-0490-4. PMID 16915381. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)



Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=WAY-100135&oldid=492539125"