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{{short description|Chemical compound}}
{{chembox
{{Chembox
⚫ | verifiedrevid = 376944058
| Verifiedfields = changed
⚫ | ImageFile = LY334370.png
| Watchedfields = changed
| ImageSize = 200px
⚫ | verifiedrevid = 439982052
⚫ | IUPACName = 4-fluoro-''N''-benzamide
⚫ | ImageFile = LY334370.svg
| ImageFile2 = LY-334370 3D BS.png
⚫ | PIN = 4-Fluoro-''N''-benzamide
| OtherNames = LY-334,370 | OtherNames = LY-334,370
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=182563-08-2 | CASNo = 182563-08-2
⚫ | PubChem=5311258
| UNII_Ref = {{fdacite|correct|FDA}}
| IUPHAR_ligand = 151
| UNII = 5Q7I1WL2UY
⚫ | PubChem = 5311258
| IUPHAR_ligand2 = 151
| IUPHAR_ligand = 20 | IUPHAR_ligand = 20
| SMILES=CN1CCC(c2c3cc(N()C(c4ccc(F)cc4)=O)ccc3n()c2)CC1 | SMILES = CN1CCC(c2c3cc(N()C(c4ccc(F)cc4)=O)ccc3n()c2)CC1
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ }}
| ChemSpiderID = 4470773
⚫ | Section2 = {{Chembox Properties
| InChI = 1/C21H22FN3O/c1-25-10-8-14(9-11-25)19-13-23-20-7-6-17(12-18(19)20)24-21(26)15-2-4-16(22)5-3-15/h2-7,12-14,23H,8-11H2,1H3,(H,24,26)
| Formula=C<sub>21</sub>H<sub>22</sub>FN<sub>3</sub>O
| InChIKey = MDMJLMDBRQXOOI-UHFFFAOYAA
| MolarMass=351.42 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| Appearance=
| StdInChI = 1S/C21H22FN3O/c1-25-10-8-14(9-11-25)19-13-23-20-7-6-17(12-18(19)20)24-21(26)15-2-4-16(22)5-3-15/h2-7,12-14,23H,8-11H2,1H3,(H,24,26)
| Density=
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| MeltingPt=
| StdInChIKey = MDMJLMDBRQXOOI-UHFFFAOYSA-N
| BoilingPt=
| RTECS =
⚫ | Solubility=
| MeSHName = C108218
⚫ }}
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ |Section2={{Chembox Properties
| MainHazards=
| C=21 | H=22 | F=1 | N=3 | O=1
| FlashPt=
| Appearance =
| Autoignition=
| Density =
⚫ }}
| MeltingPt =
| BoilingPt =
⚫ | Solubility =
⚫ }}
⚫ |Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''LY-334,370''' is a selective ] receptor ]<ref name="pmid9641544">{{cite journal | author = Dupuis DS, Colpaert FC, Pauwels PJ | title = G-protein activation at 5-HT<sub>1A</sub> receptors by the 5-HT<sub>1F</sub> ligand LY-334,370 in guinea-pig brain sections and recombinant cell lines | journal = Br. J. Pharmacol. | volume = 124 | issue = 2 | pages = 283–90 | year = 1998 | pmid = 9641544 | doi = 10.1038/sj.bjp.0701832 | issn = }}</ref> which was under development by ] for the treatment of ] headaches.<ref name="pmid10668103">{{cite journal | author = Shepheard S, Edvinsson L, Cumberbatch M, Williamson D, Mason G, Webb J, Boyce S, Hill R, Hargreaves R | title = Possible antimigraine mechanisms of action of the 5HT<sub>1F</sub> receptor agonist LY-334,370 | journal = Cephalalgia | volume = 19 | issue = 10 | pages = 851–8 | year = 1999 | pmid = 10668103 | doi = 10.1046/j.1468-2982.1999.1910851.x | issn = }}</ref> The drug showed efficacy in a phase II clinical trial<ref name="pmid11675061">{{cite journal | author = Goldstein DJ, Roon KI, Offen WW, Ramadan NM, Phebus LA, Johnson KW, Schaus JM, Ferrari MD | title = Selective seratonin 1F (5-HT<sub>1F</sub>) receptor agonist LY334370 for acute migraine: a randomised controlled trial | journal = Lancet | volume = 358 | issue = 9289 | pages = 1230–4 | year = 2001 | pmid = 11675061 | doi = 10.1016/S0140-6736(01)06347-4 | issn = }}</ref> but further development was halted due to toxicity detected in animals.<ref name="pmid16797716">{{cite journal | author = Ramadan NM, Buchanan TM | title = New and future migraine therapy | journal = Pharmacol. Ther. | volume = 112 | issue = 1 | pages = 199–212 | year = 2006 | pmid = 16797716 | doi = 10.1016/j.pharmthera.2005.04.010 | issn = }}</ref> '''LY-334370''' is a selective ] ]<ref name="pmid9641544">{{cite journal |vauthors=Dupuis DS, Colpaert FC, Pauwels PJ | title = G-protein activation at 5-HT<sub>1A</sub> receptors by the 5-HT<sub>1F</sub> ligand LY-334,370 in guinea-pig brain sections and recombinant cell lines | journal = Br. J. Pharmacol. | volume = 124 | issue = 2 | pages = 283–90 | year = 1998 | pmid = 9641544 | doi = 10.1038/sj.bjp.0701832 | pmc=1565387}}</ref> which was under development by ] for the treatment of ] headaches.<ref name="pmid10668103">{{cite journal |vauthors=Shepheard S, Edvinsson L, Cumberbatch M, Williamson D, Mason G, Webb J, Boyce S, Hill R, Hargreaves R | title = Possible antimigraine mechanisms of action of the 5HT<sub>1F</sub> receptor agonist LY-334,370 | journal = Cephalalgia | volume = 19 | issue = 10 | pages = 851–8 | year = 1999 | pmid = 10668103 | doi = 10.1046/j.1468-2982.1999.1910851.x | s2cid = 8439008 }}</ref> The drug showed efficacy in a phase II clinical trial<ref name="pmid11675061">{{cite journal |vauthors=Goldstein DJ, Roon KI, Offen WW, Ramadan NM, Phebus LA, Johnson KW, Schaus JM, Ferrari MD | title = Selective seratonin 1F (5-HT<sub>1F</sub>) receptor agonist LY334370 for acute migraine: a randomised controlled trial | journal = Lancet | volume = 358 | issue = 9289 | pages = 1230–4 | year = 2001 | pmid = 11675061 | doi = 10.1016/S0140-6736(01)06347-4 | s2cid = 39926402 }}</ref> but further development was halted due to toxicity detected in animals.<ref name="pmid16797716">{{cite journal |vauthors=Ramadan NM, Buchanan TM | title = New and future migraine therapy | journal = Pharmacol. Ther. | volume = 112 | issue = 1 | pages = 199–212 | year = 2006 | pmid = 16797716 | doi = 10.1016/j.pharmthera.2005.04.010 }}</ref>


==See also== ==See also==
* ]
* ], another 5-HT<sub>1F</sub> agonist for the treatment of migraine
* ]
* ]


==References== ==References==
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* {{MeshName|4-fluoro-N-(3-(1-methyl-4-piperidinyl)-1H-indol-5-yl)benzamide}} * {{MeshName|4-fluoro-N-(3-(1-methyl-4-piperidinyl)-1H-indol-5-yl)benzamide}}


{{Serotonin receptor modulators}}
{{Serotonergics}}


] ]
] ]
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] ]
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{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}

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Latest revision as of 12:25, 5 September 2024

Chemical compound
LY-334370
Names
Preferred IUPAC name 4-Fluoro-N-benzamide
Other names LY-334,370
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
IUPHAR/BPS
MeSH C108218
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H22FN3O/c1-25-10-8-14(9-11-25)19-13-23-20-7-6-17(12-18(19)20)24-21(26)15-2-4-16(22)5-3-15/h2-7,12-14,23H,8-11H2,1H3,(H,24,26)Key: MDMJLMDBRQXOOI-UHFFFAOYSA-N
  • InChI=1/C21H22FN3O/c1-25-10-8-14(9-11-25)19-13-23-20-7-6-17(12-18(19)20)24-21(26)15-2-4-16(22)5-3-15/h2-7,12-14,23H,8-11H2,1H3,(H,24,26)Key: MDMJLMDBRQXOOI-UHFFFAOYAA
SMILES
  • CN1CCC(c2c3cc(N()C(c4ccc(F)cc4)=O)ccc3n()c2)CC1
Properties
Chemical formula C21H22FN3O
Molar mass 351.425 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

LY-334370 is a selective 5-HT1F receptor agonist which was under development by Eli Lilly and Company for the treatment of migraine headaches. The drug showed efficacy in a phase II clinical trial but further development was halted due to toxicity detected in animals.

See also

References

  1. Dupuis DS, Colpaert FC, Pauwels PJ (1998). "G-protein activation at 5-HT1A receptors by the 5-HT1F ligand LY-334,370 in guinea-pig brain sections and recombinant cell lines". Br. J. Pharmacol. 124 (2): 283–90. doi:10.1038/sj.bjp.0701832. PMC 1565387. PMID 9641544.
  2. Shepheard S, Edvinsson L, Cumberbatch M, Williamson D, Mason G, Webb J, Boyce S, Hill R, Hargreaves R (1999). "Possible antimigraine mechanisms of action of the 5HT1F receptor agonist LY-334,370". Cephalalgia. 19 (10): 851–8. doi:10.1046/j.1468-2982.1999.1910851.x. PMID 10668103. S2CID 8439008.
  3. Goldstein DJ, Roon KI, Offen WW, Ramadan NM, Phebus LA, Johnson KW, Schaus JM, Ferrari MD (2001). "Selective seratonin 1F (5-HT1F) receptor agonist LY334370 for acute migraine: a randomised controlled trial". Lancet. 358 (9289): 1230–4. doi:10.1016/S0140-6736(01)06347-4. PMID 11675061. S2CID 39926402.
  4. Ramadan NM, Buchanan TM (2006). "New and future migraine therapy". Pharmacol. Ther. 112 (1): 199–212. doi:10.1016/j.pharmthera.2005.04.010. PMID 16797716.

External links

Serotonin receptor modulators
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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