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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| IUPAC_name = 8-fluoro-2-(3-pyridin-3-ylpropyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole
| IUPAC_name = 8-fluoro-2-(3-pyridin-3-ylpropyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole
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<!--Chemical data-->
<!--Chemical data-->
| C=19 | H=20 | F=1 | N=3
| C=19 | H=20 | F=1 | N=3
| molecular_weight = 309.38 g/mol
| smiles = Fc2cc1c3c([nH]c1cc2)CCN(C3)CCCc4cccnc4
| smiles = Fc2cc1c3c([nH]c1cc2)CCN(C3)CCCc4cccnc4
}}
}}


'''Gevotroline''' ('''WY-47,384''') is an [[atypical antipsychotic]] with a [[tricyclic]] [[chemical structure|structure]] which was under development for the treatment of [[schizophrenia]] by [[Wyeth-Ayerst]].<ref name="isbn0-412-46630-9">{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | pages = | isbn = 0-412-46630-9 | oclc = | doi = | url = https://books.google.com/books?id=Z_mfTTIApVEC&printsec=frontcover#}}</ref><ref name="isbn0-12-040525-3">{{cite book | author = Bristol, James A. | title = Annual Reports in Medicinal Chemistry (Volume 25) | publisher = Academic Press | location = Boston | year = 1990 | pages = | isbn = 0-12-040525-3 | oclc = | doi = | url = https://books.google.com/books?id=NZZbEkldeJAC&lpg=PA2&dq=gevotroline&pg=PA2#v=onepage&q}}</ref><ref name="isbn0-8493-7632-7">{{cite book |author1=Stone, T. W. |author2=Stone, Trevor | title = CNS neurotransmitters and neuromodulators: dopamine | publisher = CRC Press | location = Boca Raton | year = 1996 | pages = | isbn = 0-8493-7632-7 | oclc = | doi = | url = https://books.google.com/books?id=ObG24oxrivEC&lpg=PA187&dq=gevotroline&pg=PA187#v=onepage&q}}</ref> It acts as a balanced, modest [[affinity (pharmacology)|affinity]] [[D2 receptor|D<sub>2</sub>]] and [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[receptor antagonist|antagonist]] and also possesses high [[affinity (pharmacology)|affinity]] for the [[sigma receptor]].<ref name="isbn0-12-040525-3" /><ref name="pmid2577720">{{cite journal |vauthors=Snyder SH, Largent BL | title = Receptor mechanisms in antipsychotic drug action: focus on sigma receptors | journal = The Journal of Neuropsychiatry and Clinical Neurosciences | volume = 1 | issue = 1 | pages = 7–15 | year = 1989 | pmid = 2577720 | doi = 10.1176/jnp.1.1.7| url = }}</ref><ref name="pmid1675451">{{cite journal |vauthors=Matheson GK, Guthrie D, Bauer C, Knowles A, White G, Ruston C | title = Sigma receptor ligands alter concentrations of corticosterone in plasma in the rat | journal = Neuropharmacology | volume = 30 | issue = 1 | pages = 79–87 |date=January 1991 | pmid = 1675451 | doi = 10.1016/0028-3908(91)90046-E| url = }}</ref><ref name="pmid1348112">{{cite journal |vauthors=Gudelsky GA, Nash JF | title = Neuroendocrinological and neurochemical effects of sigma ligands | journal = Neuropharmacology | volume = 31 | issue = 2 | pages = 157–62 |date=February 1992 | pmid = 1348112 | doi = 10.1016/0028-3908(92)90026-L| url = }}</ref> It was well-tolerated and showed efficacy in [[clinical trial#Phase II|phase II]] [[clinical trial]]s but was never marketed.<ref name="isbn0-12-040525-3" /><ref name="isbn0-8493-7632-7" />
'''Gevotroline''' ('''WY-47,384''') is an [[atypical antipsychotic]] with a [[tricyclic]] [[chemical structure|structure]] which was under development for the treatment of [[schizophrenia]] by [[Wyeth-Ayerst]].<ref name="isbn0-412-46630-9">{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=Z_mfTTIApVEC}}</ref><ref name="isbn0-12-040525-3">{{cite journal | vauthors = Abou-Gharbia M, Moyer JA | title = Novel Antipyschotic Agents| veditors = Bristol JA | journal = Annual Reports in Medicinal Chemistry | volume = 25 | pages = 1–10 | publisher = Academic Press | location = Boston | year = 1990 | isbn = 0-12-040525-3 | doi = 10.1016/S0065-7743(08)61577-8 | url = https://books.google.com/books?id=NZZbEkldeJAC&q=gevotroline&pg=PA2}}</ref><ref name="isbn0-8493-7632-7">{{cite book | vauthors = Jackson DM, Mohell N | chapter = A Review of the Pharmacology of New Antipsychotic Drugs| veditors = Stone TW | title = CNS neurotransmitters and neuromodulators: dopamine | publisher = CRC Press | location = Boca Raton | year = 1996 | isbn = 0-8493-7632-7 | chapter-url = https://books.google.com/books?id=ObG24oxrivEC&q=gevotroline&pg=PA187}}</ref> It acts as a balanced, modest [[affinity (pharmacology)|affinity]] [[D2 receptor|D<sub>2</sub>]] and [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[receptor antagonist|antagonist]] and also possesses high [[affinity (pharmacology)|affinity]] for the [[sigma receptor]].<ref name="isbn0-12-040525-3" /><ref name="pmid2577720">{{cite journal | vauthors = Snyder SH, Largent BL | title = Receptor mechanisms in antipsychotic drug action: focus on sigma receptors | journal = The Journal of Neuropsychiatry and Clinical Neurosciences | volume = 1 | issue = 1 | pages = 7–15 | year = 1989 | pmid = 2577720 | doi = 10.1176/jnp.1.1.7 }}</ref><ref name="pmid1675451">{{cite journal | vauthors = Matheson GK, Guthrie D, Bauer C, Knowles A, White G, Ruston C | title = Sigma receptor ligands alter concentrations of corticosterone in plasma in the rat | journal = Neuropharmacology | volume = 30 | issue = 1 | pages = 79–87 | date = January 1991 | pmid = 1675451 | doi = 10.1016/0028-3908(91)90046-E | s2cid = 29702968 }}</ref><ref name="pmid1348112">{{cite journal | vauthors = Gudelsky GA, Nash JF | title = Neuroendocrinological and neurochemical effects of sigma ligands | journal = Neuropharmacology | volume = 31 | issue = 2 | pages = 157–162 | date = February 1992 | pmid = 1348112 | doi = 10.1016/0028-3908(92)90026-L | s2cid = 36585024 }}</ref> It was well tolerated and showed efficacy in [[clinical trial#Phase II|phase II]] [[clinical trial]]s but was never marketed.<ref name="isbn0-12-040525-3" /><ref name="isbn0-8493-7632-7" />


== See also ==
== See also ==
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[[Category:Atypical antipsychotics]]
[[Category:Atypical antipsychotics]]
[[Category:Fluoroarenes]]
[[Category:Fluoroarenes]]
[[Category:Pyridines]]
[[Category:3-Pyridyl compounds]]
[[Category:Pyridoindoles]]
[[Category:Pyridoindoles]]
[[Category:Gamma-Carbolines]]

Latest revision as of 06:51, 15 December 2023

Gevotroline
Clinical data
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 8-fluoro-2-(3-pyridin-3-ylpropyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20FN3
Molar mass309.388 g·mol−1
3D model (JSmol)
  • Fc2cc1c3c([nH]c1cc2)CCN(C3)CCCc4cccnc4

Gevotroline (WY-47,384) is an atypical antipsychotic with a tricyclic structure which was under development for the treatment of schizophrenia by Wyeth-Ayerst.[1][2][3] It acts as a balanced, modest affinity D2 and 5-HT2 receptor antagonist and also possesses high affinity for the sigma receptor.[2][4][5][6] It was well tolerated and showed efficacy in phase II clinical trials but was never marketed.[2][3]

See also

[edit]

References

[edit]
  1. ^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
  2. ^ a b c Abou-Gharbia M, Moyer JA (1990). Bristol JA (ed.). "Novel Antipyschotic Agents". Annual Reports in Medicinal Chemistry. 25. Boston: Academic Press: 1–10. doi:10.1016/S0065-7743(08)61577-8. ISBN 0-12-040525-3.
  3. ^ a b Jackson DM, Mohell N (1996). "A Review of the Pharmacology of New Antipsychotic Drugs". In Stone TW (ed.). CNS neurotransmitters and neuromodulators: dopamine. Boca Raton: CRC Press. ISBN 0-8493-7632-7.
  4. ^ Snyder SH, Largent BL (1989). "Receptor mechanisms in antipsychotic drug action: focus on sigma receptors". The Journal of Neuropsychiatry and Clinical Neurosciences. 1 (1): 7–15. doi:10.1176/jnp.1.1.7. PMID 2577720.
  5. ^ Matheson GK, Guthrie D, Bauer C, Knowles A, White G, Ruston C (January 1991). "Sigma receptor ligands alter concentrations of corticosterone in plasma in the rat". Neuropharmacology. 30 (1): 79–87. doi:10.1016/0028-3908(91)90046-E. PMID 1675451. S2CID 29702968.
  6. ^ Gudelsky GA, Nash JF (February 1992). "Neuroendocrinological and neurochemical effects of sigma ligands". Neuropharmacology. 31 (2): 157–162. doi:10.1016/0028-3908(92)90026-L. PMID 1348112. S2CID 36585024.
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