Capsazepine

A TRPV1 antagonist

Transient receptor potential vanilloid type 1 (TRPV1) is a member of the transient receptor potential (TRP) family that is activated or sensitized by a variety of endogenous stimuli as a result of tissue injury and inflammation. TRPV1 is upregulated during inflammation and plays a role in the perception of pain.1,2 Capsazepine is a competitive antagonist of transient receptor potential vanilloid type 1 (TRPV1) which blocks the capsaicin-induced uptake of Ca2+ in neonatal rat dorsal root ganglia with an IC50 of 0.42 µM and Chinese hamster ovary cells with an IC50 of 17 nM.1,3 It does not block acid- or heat-induced activation of TRPV1 and may block receptors other than TRPV1.4,5

376.9

≥98%

OC1=C(O)C=C(CCCN(C(N([H])CCC2=CC=C(Cl)C=C2)=S)C3)C3=C1

C19H21ClN2O2S

138977-28-3

≥ 4 years

DMF: 30 mg/ml DMSO: 30 mg/ml DMSO:PBS (pH 7.2)(1:1): 0.45 mg/ml Ethanol: 20 mg/ml

1.Doherty, E.M.,Fotsch, C.,Bo, Y., et al. Discovery of potent, orally available vanilloid receptor-1 antagonists. Structure-activity relationship of N-aryl cinnamides. Journal of Medicinal Chemistry 48, 71-90 (2005).
2.Walker, K.M.,Urban, L.,Medhurst, S.J., et al. The VR1 antagonist capsazepine reverses mechanical hyperalgesia in models of inflammatory and neuropathic pain. Journal of Pharmacology and Experimental Therapeutics 304(1), 56-60 (2003).
3.Walpole, S.J.,Bevan, S.,Bovermann, G., et al. The discovery of capsazepine, the first competitive antagonist of the sensory neuron excitants capsaicin and resiniferatoxin. Journal of Medicinal Chemistry 37, 1942-1954 (1994).
4.Liu, L., and Simon, S.A. Capsazepine, a vanilloid receptor antagonist, inhibits nicotinic acetylcholine receptors in rat trigeminal ganglia. Neuroscience Letters 228, 29-32 (1997).
5.Docherty, R.J.,Yeats, J.C., and Piper, A.S. Capsazepine block of voltage-activated calcium channels in adult rat dorsal root ganglion neurones in culture. British Journal of Pharmacology 121, 1461-1467 (1997).