Capsazepine

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ImageFile1 = Capsazepine.png ImageSize1 = 250px
IUPACName = N- [2-(4-Chlorophenyl)ethyl] -1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide
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CASNo = 138977-28-3
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Formula = C₁₉H₂₁ClN₂O₂S
MolarMass = 376.9 g/mol
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Capsazepine is a synthetic analogue of capsaicin.

Pharmacaology

Capsazepine blocks the painful sensation of heat caused by capsaicin (the active ingredient of chilli pepper) which activates the TRPV1 ion channel. It is therefore considered to be a capsaicin antagonist. The TRPV1 channel functions as a pain and temperature sensor in mammalians. Capsazepine blocks only the activation of TRPV1 channels by chemicals but not by other painful stimuli, like heat. Depending on the pharmacological assay the half maximal inhibitory concentration IC50 is in the nanomolar to low micromolar range. It addition to its effects on TRPV1 channels it was also shown to inhibit voltage-activated calcium channelscite journal |author=Docherty RJ, Yeats JC, Piper AS |title=Capsazepine block of voltage-activated calcium channels in adult rat dorsal root ganglion neurones in culture |journal=British journal of pharmacology |volume=121 |issue=7 |pages=1461–7 |year=1997 |month=August |pmid=9257928 |pmc=1564831 |doi=10.1038/sj.bjp.0701272 |url=] and nicotinic acetylcholine receptors.cite journal |author=Liu L, Simon SA |title=Capsazepine, a vanilloid receptor antagonist, inhibits nicotinic acetylcholine receptors in rat trigeminal ganglia |journal=Neuroscience letters |volume=228 |issue=1 |pages=29–32 |year=1997 |month=May |pmid=9197280 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/S0304394097003583] It mainly serves as a tool to study the TRPV1 ion channel.cite journal |author=Valenzano KJ, Sun Q |title=Current perspectives on the therapeutic utility of VR1 antagonists |journal=Current medicinal chemistry |volume=11 |issue=24 |pages=3185–202 |year=2004 |month=December |pmid=15579007 |doi= |url=http://www.bentham-direct.org/pages/content.php?CMC/2004/00000011/00000024/0003C.SGM]

Development

Capsazepine was discovered by a research group at the Sandoz Institute for Medical Research. Its synthesis and chemical properties were published in 1994. It was found by modification of the chemical backbone of capsaicin.cite journal |author=Walpole CS, Bevan S, Bovermann G, "et al" |title=The discovery of capsazepine, the first competitive antagonist of the sensory neuron excitants capsaicin and resiniferatoxin |journal=Journal of medicinal chemistry |volume=37 |issue=13 |pages=1942–54 |year=1994 |month=June |pmid=8027976 |doi= |url=]

Links

* [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1422598&dopt=Abstract Initial Study on PubMed]

References