CAPSAZEPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H21ClN2O2S
Molecular Weight	376.9
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(O)C=C2CN(CCCC2=C1)C(=S)NCCC3=CC=C(Cl)C=C3

InChI

InChIKey=DRCMAZOSEIMCHM-UHFFFAOYSA-N

InChI=1S/C19H21ClN2O2S/c20-16-5-3-13(4-6-16)7-8-21-19(25)22-9-1-2-14-10-17(23)18(24)11-15(14)12-22/h3-6,10-11,23-24H,1-2,7-9,12H2,(H,21,25)

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Amiloride-sensitive sodium channel, ENaC 4 Target ID: CHEMBL2107836 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15308635	Activator 1447		8.0 µM [EC50]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27356469	Antagonist 2849		3.2 µM [Ki]

PubMed

Title	Date	PubMed
Characterization of the vanilloid receptor 1 antagonist iodo-resiniferatoxin on the afferent and efferent function of vagal sensory C-fibers.	2002-11	12388656
Cellular mechanisms of nociception in the frog.	2002-10	12364510
Anandamide is a partial agonist at native vanilloid receptors in acutely isolated mouse trigeminal sensory neurons.	2002-10	12359623
High affinity antagonists of the vanilloid receptor.	2002-10	12237342
Effect of piperine, the active ingredient of black pepper, on intestinal secretion in mice.	2002-09-27	12215378
Protein kinase C(alpha) is required for vanilloid receptor 1 activation. Evidence for multiple signaling pathways.	2002-09-20	12095983
Vanilloid receptors presynaptically modulate cranial visceral afferent synaptic transmission in nucleus tractus solitarius.	2002-09-15	12223576
Mechanisms of acid-induced activation of airway afferent nerve fibres in guinea-pig.	2002-09-01	12205192
Capsaicin activation of glutamatergic synaptic transmission in the rat locus coeruleus in vitro.	2002-09-01	12205187
Phosphorylation of extracellular signal-regulated kinase in primary afferent neurons by noxious stimuli and its involvement in peripheral sensitization.	2002-09-01	12196597
Prostaglandin and protein kinase A-dependent modulation of vanilloid receptor function by metabotropic glutamate receptor 5: potential mechanism for thermal hyperalgesia.	2002-09-01	12196566
Pharmacological separation of cannabinoid sensitive receptors on hippocampal excitatory and inhibitory fibers.	2002-09	12367597
Cloning and functional characterization of the guinea pig vanilloid receptor 1.	2002-09	12243775
Characterization of the anandamide induced depolarization of guinea-pig isolated vagus nerve.	2002-09	12183329
Mechanisms underlying tissue selectivity of anandamide and other vanilloid receptor agonists.	2002-09	12181448
Binding, degradation and apoptotic activity of stearoylethanolamide in rat C6 glioma cells.	2002-08-15	12010121
The cardioprotection of rutaecarpine is mediated by endogenous calcitonin related-gene peptide through activation of vanilloid receptors in guinea-pig hearts.	2002-08	12221592
Activation of capsaicin receptors on the sciatic nerve induces FOS expression in the spinal dorsal horn of adult rats.	2002-07-26	12138252
Effects of peripheral nerve injury on functional spinal VR1 receptors.	2002-07-02	12151758
Activation of protein kinase C sensitizes human VR1 to capsaicin and to moderate decreases in pH at physiological temperatures in Xenopus oocytes.	2002-07	12098622
A heat-sensitive TRP channel expressed in keratinocytes.	2002-06-14	12016205
Capsazepine inhibits thermal hyperalgesia but not nociception triggered by protease-activated receptor-2 in rats.	2002-06	12120762
DRASIC contributes to pH-gated currents in large dorsal root ganglion sensory neurons by forming heteromultimeric channels.	2002-06	12037186
The arginine-rich hexapeptide R4W2 is a stereoselective antagonist at the vanilloid receptor 1: a Ca2+ imaging study in adult rat dorsal root ganglion neurons.	2002-06	12023528
Anandamide-induced vasorelaxation in rabbit aortic rings has two components: G protein dependent and independent.	2002-06	12003810
Ethanol elicits and potentiates nociceptor responses via the vanilloid receptor-1.	2002-06	11992116
Comparison of capsaicin-evoked calcium transients between rat nodose and jugular ganglion neurons.	2002-05-31	12132648
Contractile response to a cannabimimetic eicosanoid, 2-arachidonoylglycerol, of longitudinal smooth muscle from the guinea-pig distal colon in vitro.	2002-05-31	12063081
Spinal administration of capsazepine inhibits noxious evoked responses of dorsal horn neurons in non-inflamed and carrageenan inflamed rats.	2002-05-10	12062478
Gastric hyperemic response induced by acid back-diffusion in rat stomachs following barrier disruption -- relation to vanilloid type-1 receptors.	2002-05	12011761
3-D-QSAR analysis of N-(3-acyloxy-2-benzylpropyl)-N'-dihydroxytetrahydrobenzazepine and tetrahydroisoquinoline and N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thioureas analogues as potent vanilloid receptor ligands.	2002-05	11886800
Ischemia/reperfusion-induced increase in the hepatic level of prostacyclin is mainly mediated by activation of capsaicin-sensitive sensory neurons in rats.	2002-04	12024109
Capsazepine partially inhibits neurally mediated gastric mucus secretion following activation of protease-activated receptor 2.	2002-04	11985550
Arvanil-induced inhibition of spasticity and persistent pain: evidence for therapeutic sites of action different from the vanilloid VR1 receptor and cannabinoid CB(1)/CB(2) receptors.	2002-03-29	11937096
Interaction between vanilloid and glutamate receptors in the central modulation of nociception.	2002-03-29	11937094
Stimulation of pulmonary vagal C-fibres by anandamide in anaesthetized rats: role of vanilloid type 1 receptors.	2002-03-15	11897863
Protease-activated receptor-2 activation causes EDHF-like coronary vasodilation: selective preservation in ischemia/reperfusion injury: involvement of lipoxygenase products, VR1 receptors, and C-fibers.	2002-03-08	11884377
Relaxant effect of capsazepine in the isolated rat ileum.	2002-03	11882914
Evidence of a novel site mediating anandamide-induced negative inotropic and coronary vasodilatator responses in rat isolated hearts.	2002-03	11877326
Functional vanilloid receptors in cultured normal human epidermal keratinocytes.	2002-02-15	11829471
Particulate matter inflammation and receptor sensitivity are target cell specific.	2002-02	12122578
Pharmacological characterization of vanilloid receptor located in the brain.	2002-01-31	11834295
Simultaneous intracellular calcium and sodium flux imaging in human vanilloid receptor 1 (VR1)-transfected human embryonic kidney cells: a method to resolve ionic dependence of VR1-mediated cell death.	2002-01	11752091
Effects of ginsenosides on vanilloid receptor (VR1) channels expressed in Xenopus oocytes.	2001-12-31	11804333
Acidic stimuli activates two distinct pathways in taste receptor cells from rat fungiform papillae.	2001-12-27	11743973
Anandamide and methanandamide induce both vanilloid VR1- and cannabinoid CB1 receptor-mediated changes in heart rate and blood pressure in anaesthetized rats.	2001-12	11770012
The endogenous cannabinoid anandamide activates vanilloid receptors in the rat hippocampal slice.	2001-12	11747904
Involvement of vanilloid receptor VR1 and prostanoids in the acid-induced writhing responses of mice.	2001-11-02	11720094
Capsaicin-, resiniferatoxin-, and olvanil-induced adrenaline secretions in rats via the vanilloid receptor.	2001-11	11791717
CH-19 sweet, nonpungent cultivar of red pepper, increased body temperature in mice with vanilloid receptors stimulation by capsiate.	2001-08	11767210

Patents

Name

Type

Language

CAPSAZEPINE

Common Name

English

N-(2-(4-CHLOROPHENYL)ETHYL)-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE

Preferred Name

English

Code System Code Type Description

WIKIPEDIA

Capsazepine