5-Fluorowillardiine

5-Fluorowillardiine

Names
Other names 2-Amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid
Identifiers
CAS Number	140187-23-1 (S)
3D model (Jmol)	Interactive image
ChEBI	CHEBI:42549
ChEMBL	ChEMBL123132
ChemSpider	1259 112461 (S)
DrugBank	DB02966
ECHA InfoCard	100.162.280
MeSH	5-Fluorowillardiine
PubChem	1299 126569 (S)
InChI InChI=1S/C7H8FN3O4/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12/h1,4H,2,9H2,(H,13,14)(H,10,12,15) Key: DBWPFHJYSTVBCZ-UHFFFAOYSA-N InChI=1/C7H8FN3O4/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12/h1,4H,2,9H2,(H,13,14)(H,10,12,15) Key: DBWPFHJYSTVBCZ-UHFFFAOYAR
SMILES NC(CN1C=C(F)C(=O)N=C1O)C(O)=O
Properties
Chemical formula	C7H8FN3O4
Molar mass	217.16 g·mol^−1
log P	-1.168
Acidity (pKa)	2.118
Basicity (pKb)	11.879
Isoelectric point	4.28
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

5-Fluorowillardiine is a selective agonist for the AMPA receptor,^[1][2][3] with only limited effects at the kainate receptor.^[4] It is an excitotoxic neurotoxin when used in vivo and so is rarely used in intact animals, but it is widely used to selectively stimulate AMPA receptors in vitro.^[5][6][7]

5-Fluorowillardiine exists as two distinct isomers:

• (2R) or D
• (2S) or L

References

1. Patneau, DK; Mayer, ML; Jane, DE; Watkins, JC (1992). "Activation and Desensitization of AMPA / Kainate Receptors by Novel Derivatives of Willardiine" (PDF). Journal of Neuroscience. 12 (2): 595–606. PMID 1371315.
2. Hawkins, LM; Beaver, KM; Jane, DE; Taylor, PM; Sunter, DC; Roberts, PJ (1995). "Characterization of the pharmacology and regional distribution of (S)-³H-5-fluorowillardiine binding in rat brain". British Journal of Pharmacology. 116 (3): 2033–9. doi:10.1111/j.1476-5381.1995.tb16408.x. PMC 1908955. PMID 8640342.
3. Lunn, ML; Ganakas, AM; Mercer, LD; Lawrence, AJ; Beart, PM (1996). "Localisation and properties of AMPA-insensitive kainate sites: receptor autoradiography and gene expression in rat brain". Neuroscience Letters. 204 (1–2): 121–4. doi:10.1016/0304-3940(96)12335-1. PMID 8929993.
4. Larm, JA; Cheung, NS; Beart, PM (1996). "(S)-5-fluorowillardiine-mediated neurotoxicity in cultured murine cortical neurones occurs via AMPA and kainate receptors". European Journal of Pharmacology. 314 (1–2): 249–54. doi:10.1016/S0014-2999(96)00633-4. PMID 8957243.
5. Jensen, RJ (1999). "Responses of directionally selective retinal ganglion cells to activation of AMPA glutamate receptors". Visual Neuroscience. 16 (2): 205–19. doi:10.1017/s0952523899162023. PMID 10367956.
6. Olivera, S; Rodriguez-Ithurralde, D; Henley, JM (2001). "Regional localization and developmental profile of acetylcholinesterase-evoked increases in ³H-5-fluorowillardiine binding to AMPA receptors in rat brain". British Journal of Pharmacology. 133 (7): 1055–62. doi:10.1038/sj.bjp.0704167. PMC 1572873. PMID 11487516.
7. Kessler, M; Arai, AC (2006). "Use of ³H fluorowillardiine to study properties of AMPA receptor allosteric modulators". Brain Research. 1076 (1): 25–41. doi:10.1016/j.brainres.2005.09.024. PMID 16256076.