(S)-(-)-5-Fluorowillardiine (Synonyms: (5S)-Fluorowillardiine; (S)-5-Fluorowillardiine)

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(S)-(-)-5-Fluorowillardiine ((5S)-Fluorowillardiine; (S)-5-Fluorowillardiine) is a potent, highly selective non-NMDA ionotropic glutamate receptor (iGluR, AMPA/Kainate receptor) agonist. (S)-(-)-5-Fluorowillardiine activates high-affinity AMPA-preferring receptors (EC₅₀ = 0.70 μM) and low-affinity kainate-preferring receptors (EC₅₀ = 170 μM), thereby inducing biphasic dose-dependent neurotoxicity/excitotoxicity. (S)-(-)-5-Fluorowillardiine is applicable to research related to schizophrenia, temporal lobe epilepsy, and bipolar disorder.

For research use only. We do not sell to patients.

(S)-(-)-5-Fluorowillardiine Chemical Structure

CAS No. : 140187-23-1

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5 mg	Get quote 2 - 3 weeks 1 - 2 Weeks 3 - 4 weeks 2 - 3 weeks	Estimated Time of Arrival: December 31
10 mg	Get quote 2 - 3 weeks 1 - 2 Weeks 3 - 4 weeks 2 - 3 weeks	Estimated Time of Arrival: December 31
25 mg	Get quote 2 - 3 weeks 1 - 2 Weeks 3 - 4 weeks 2 - 3 weeks	Estimated Time of Arrival: December 31
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Other Forms of (S)-(-)-5-Fluorowillardiine:

(S)-(-)-5-Fluorowillardiine (hydrochloride) In-stock

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AMPA Receptor NMDA Receptor Kainate Receptor

Biological Activity
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target

AMPA Receptor

Cellular Effect

Cell Line	Type	Value	Description	References
Oocyte	EC₅₀	0.38 μM Compound: (S)-2b	Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR1 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR1 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method	[PMID: 18811139]
Oocyte	EC₅₀	0.38 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA1 receptor expressed in Xenopus oocytes Agonist activity at recombinant GluA1 receptor expressed in Xenopus oocytes	[PMID: 20096591]
Oocyte	EC₅₀	0.382 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA1 receptor flip isoform expressed in Xenopus oocytes Agonist activity at recombinant GluA1 receptor flip isoform expressed in Xenopus oocytes	[PMID: 20096591]
Oocyte	EC₅₀	0.46 μM Compound: (S)-2b	Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR2(Q) expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR2(Q) expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method	[PMID: 18811139]
Oocyte	EC₅₀	0.463 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA2 receptor flip isoform expressed in Xenopus oocytes Agonist activity at recombinant GluA2 receptor flip isoform expressed in Xenopus oocytes	[PMID: 20096591]
Oocyte	EC₅₀	11.9 μM Compound: (S)-2b	Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR4 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR4 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method	[PMID: 18811139]
Oocyte	EC₅₀	11.9 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA4 receptor flip isoform expressed in Xenopus oocytes Agonist activity at recombinant GluA4 receptor flip isoform expressed in Xenopus oocytes	[PMID: 20096591]
Oocyte	EC₅₀	20.9 μM Compound: (S)-2b	Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR3 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method Agonist activity at cyclothiazide-desensitized rat recombinant flip iGluR3 expressed in Xenopus laevis oocytes by two electrode voltage-clamp electrophysiology method	[PMID: 18811139]
Oocyte	EC₅₀	20.9 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA3 receptor expressed in Xenopus oocytes Agonist activity at recombinant GluA3 receptor expressed in Xenopus oocytes	[PMID: 20096591]
Oocyte	EC₅₀	20.9 μM Compound: (S)-F-Willardiine	Agonist activity at recombinant GluA3 receptor flip isoform expressed in Xenopus oocytes Agonist activity at recombinant GluA3 receptor flip isoform expressed in Xenopus oocytes	[PMID: 20096591]

In Vitro

(S)-(-)-5-Fluorowillardiine (10-100 μM; 24 h) induces > 90% neurotoxicity in primary cultured murine cortical neurones via a biphasic mechanism, with high-affinity component activity at AMPA receptors (EC₅₀ = 0.70 μM) and low-affinity component activity at kainate receptors (EC₅₀ = 170 μM)^[1].
(S)-(-)-5-Fluorowillardiine (200 nM-60 μM) potently activates AMPA/kainate receptors on primary dissociated cultures of mouse embryonic hippocampal neurons with an equilibrium EC₅₀ of 1.47 μM, induces strong desensitization (92.5%), exhibits cross-desensitization with other willardiine derivatives, and produces a prolonged inward tail current following agonist removal^[2].
(S)-(-)-5-Fluorowillardiine (0.1 nM-1 mM; 2 h) binds to mouse GluK5 kainate receptor subunits expressed in Sf9 cell membranes with a K_i of 1.79 μM, and exhibits similar affinity for GluK5 and GluK1 subunits^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

217.15

Formula

C₇H₈FN₃O₄

CAS No.

140187-23-1

SMILES

OC([C@@H](N)CN1C=C(F)C(NC1=O)=O)=O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Larm JA, et al. (S)-5-fluorowillardiine-mediated neurotoxicity in cultured murine cortical neurones occurs via AMPA and kainate receptors. Eur J Pharmacol. 1996;314(1-2):249-254. [Content Brief]

[2]. Patneau DK, et al. Activation and desensitization of AMPA/kainate receptors by novel derivatives of willardiine. J Neurosci. 1992;12(2):595-606. [Content Brief]

[3]. Møllerud S, et al. A pharmacological profile of the high-affinity GluK5 kainate receptor. Eur J Pharmacol. 2016;788:315-320. [Content Brief]

(S)-(-)-5-Fluorowillardiine Related Classifications

Neurological Disease

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Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(S)-(-)-5-Fluorowillardiine140187-23-1(5S)-Fluorowillardiine (S)-5-FluorowillardiineiGluRIonotropic glutamate receptorsGluK1 kainate receptorsAMPA-preferring receptorsschizophreniaAMPA/kainate receptormurine cortical neuronesbipolar disorderkainate-preferring receptorstemporal lobe epilepsyGluK5 kainate receptorsmouse embryonic hippocampal neuronsInhibitorinhibitorinhibit

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