A-803467

Names

[ Name ]:
A-803467

[Synonym ]:
5-(4-Chlorophenyl)-N-(3,5-dimethoxyphenyl)-2-furamide
2-Furancarboxamide, 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)-
cc-433
A-803467

Biological Activity

[Description]:

A 803467 is a selective Nav1.8 sodium channel blocker with an IC50 of 8 nM; over 100-fold more selective vs. human Nav1.2, 1.3, 1.5 and 1.7. IC50 value: 8 nMTarget: Nav1.8 sodium channelA 803467 dose-dependently reduces behavioral responses in a variety of neuropathic and inflammatory pain models.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Neurological Disease

[References]

[1]. McGaraughty, et al. A selective NaV1.8 sodium channel blocker, A-803467 [5-(4-chlorophenyl-N-(3,5-dimethoxyphenyl)furan-2-carboxamide)], attenuates spinal neuronal activity in neuropathic rats. Journal of Pharmacology and Experimental Therapeutics (2008),

[2]. Jarvis MF, et al. A-803467, a potent and selective Nav1.8 sodium channel blocker, attenuates neuropathic and inflammatory pain in the rat. Proc Natl Acad Sci U S A. 2007 May 15;104(20):8520-5.

[3]. Joshi SK, et al. Additive antinociceptive effects of the selective Nav1.8 blocker A-803467 and selective TRPV1 antagonists in rat inflammatory and neuropathic pain models. http://www.ncbi.nlm.nih.gov/pubmed/19070548

[4]. Kort ME, et al. Subtype-selective Na(v)1.8 sodium channel blockers: identification of potent, orally active nicotinamide derivatives. Bioorg Med Chem Lett. 2010 Nov 15;20(22):6812-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
450.6±45.0 °C at 760 mmHg

[ Melting Point ]:
128-130?C

[ Molecular Formula ]:
C₁₉H₁₆ClNO₄

[ Molecular Weight ]:
357.788

[ Flash Point ]:
226.3±28.7 °C

[ Exact Mass ]:
357.076782

[ PSA ]:
60.70000

[ LogP ]:
4.93

[ Appearance of Characters ]:
white to tan

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
Store at +4°C

[ Water Solubility ]:
DMSO: >10mg/mL

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932190090

[ Summary ]:
2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

A-803467, a potent and selective Nav1.8 sodium channel blocker, attenuates neuropathic and inflammatory pain in the rat.

Proc. Natl. Acad. Sci. U. S. A. 104 , 8520-5, (2007)

Activation of tetrodotoxin-resistant sodium channels contributes to action potential electrogenesis in neurons. Antisense oligonucleotide studies directed against Na(v)1.8 have shown that this channel...

Painful research: identification of a small-molecule inhibitor that selectively targets Nav1.8 sodium channels.

Mol. Interv. 7 , 192-5, (2007)

Voltage-gated sodium channels in nociceptive neurons are attractive targets for novel pain therapeutics. Although drugs that target voltage-gated sodium channels have proven value as pain therapeutics...

Functional Nav1.8 channels in intracardiac neurons: the link between SCN10A and cardiac electrophysiology.

Circ. Res. 111 , 333-43, (2012)

The SCN10A gene encodes the neuronal sodium channel isoform Na(V)1.8. Several recent genome-wide association studies have linked SCN10A to PR interval and QRS duration, strongly suggesting an as-yet u...