Capsazepine
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MedKoo CAT#: 326688

CAS#: 138977-28-3

Description: Capsazepine is TRPM8 a antagonist. 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. In addition to its effects on TRPV1 channels it was also shown to inhibit the cold activated TRPM8 channel, voltage-activated calcium channels and nicotinic acetylcholine receptors. It mainly serves as a tool to study the TRPV1 ion channel.


Chemical Structure

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Capsazepine
CAS# 138977-28-3

Theoretical Analysis

MedKoo Cat#: 326688
Name: Capsazepine
CAS#: 138977-28-3
Chemical Formula: C19H21ClN2O2S
Exact Mass: 376.1012
Molecular Weight: 376.899
Elemental Analysis: C, 60.55; H, 5.62; Cl, 9.41; N, 7.43; O, 8.49; S, 8.51

Price and Availability

Size Price Availability Quantity
5.0mg USD 180.0 2 Weeks
10.0mg USD 210.0 2 Weeks
50.0mg USD 750.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 5250.0 2 Weeks
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Synonym: Capsazepine

IUPAC/Chemical Name: N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide

InChi Key: DRCMAZOSEIMCHM-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: S=C(N1CCCC2=CC(O)=C(O)C=C2C1)NCCC3=CC=C(Cl)C=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 376.899 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Cabral LD, Giusti-Paiva A. The Transient Receptor Potential Vanilloid 1 (TRPV1) Antagonist Capsazepine Improves the Impaired Lung Mechanics during Endotoxemia. Basic Clin Pharmacol Toxicol. 2016 Apr 19. doi: 10.1111/bcpt.12605. [Epub ahead of print] PubMed PMID: 27090778.

2: Naderi N, Shafieirad E, Lakpoor D, Rahimi A, Mousavi Z. Interaction between Cannabinoid Compounds and Capsazepine in Protection against Acute Pentylenetetrazole-induced Seizure in Mice. Iran J Pharm Res. 2015 Winter;14(Suppl):115-20. PubMed PMID: 26185513; PubMed Central PMCID: PMC4499434.

3: Fernandes ES, Brito CX, Teixeira SA, Barboza R, dos Reis AS, Azevedo-Santos AP, Muscará M, Costa SK, Marinho CR, Brain SD, Grisotto MA. TRPV1 antagonism by capsazepine modulates innate immune response in mice infected with Plasmodium berghei ANKA. Mediators Inflamm. 2014;2014:506450. doi: 10.1155/2014/506450. Epub 2014 Aug 24. PubMed PMID: 25242870; PubMed Central PMCID: PMC4158567.

4: Shukla A, Sharma P, Prakash O, Singh M, Kalani K, Khan F, Bawankule DU, Luqman S, Srivastava SK. QSAR and docking studies on capsazepine derivatives for immunomodulatory and anti-inflammatory activity. PLoS One. 2014 Jul 8;9(7):e100797. doi: 10.1371/journal.pone.0100797. eCollection 2014. PubMed PMID: 25003344; PubMed Central PMCID: PMC4086833.

5: Mahmmoud YA, Shattock M, Cornelius F, Pavlovic D. Inhibition of K+ transport through Na+, K+-ATPase by capsazepine: role of membrane span 10 of the α-subunit in the modulation of ion gating. PLoS One. 2014 May 9;9(5):e96909. doi: 10.1371/journal.pone.0096909. eCollection 2014. PubMed PMID: 24816799; PubMed Central PMCID: PMC4016139.

6: Gonzalez-Reyes LE, Ladas TP, Chiang CC, Durand DM. TRPV1 antagonist capsazepine suppresses 4-AP-induced epileptiform activity in vitro and electrographic seizures in vivo. Exp Neurol. 2013 Dec;250:321-32. doi: 10.1016/j.expneurol.2013.10.010. Epub 2013 Oct 18. PubMed PMID: 24145133; PubMed Central PMCID: PMC4104534.

7: Zuo GF, Li MH, Zhang JX, Li B, Wang ZM, Wang Q, Xiao H, Chen SL. Capsazepine concentration dependently inhibits currents in HEK 293 cells mediated by human hyperpolarization-activated cyclic nucleotide-gated 2 and 4 channels. Exp Biol Med (Maywood). 2013 Sep;238(9):1055-61. doi: 10.1177/1535370213498973. PubMed PMID: 24048192.

8: Zuo X, Ling JX, Xu GY, Gu JG. Operant behavioral responses to orofacial cold stimuli in rats with chronic constrictive trigeminal nerve injury: effects of menthol and capsazepine. Mol Pain. 2013 Jun 14;9:28. doi: 10.1186/1744-8069-9-28. PubMed PMID: 23767981; PubMed Central PMCID: PMC3750444.

9: Sung B, Prasad S, Ravindran J, Yadav VR, Aggarwal BB. Capsazepine, a TRPV1 antagonist, sensitizes colorectal cancer cells to apoptosis by TRAIL through ROS-JNK-CHOP-mediated upregulation of death receptors. Free Radic Biol Med. 2012 Nov 15;53(10):1977-87. doi: 10.1016/j.freeradbiomed.2012.08.012. Epub 2012 Aug 15. PubMed PMID: 22922338; PubMed Central PMCID: PMC3731040.

10: Olszewska J, Tęgowska E. Opposite effect of capsaicin and capsazepine on behavioral thermoregulation in insects. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2011 Oct;197(10):1021-6. doi: 10.1007/s00359-011-0657-2. Epub 2011 Jun 11. PubMed PMID: 21667066; PubMed Central PMCID: PMC3176404.

11: Luqman S, Meena A, Marler LE, Kondratyuk TP, Pezzuto JM. Suppression of tumor necrosis factor-α-induced nuclear factor κB activation and aromatase activity by capsaicin and its analog capsazepine. J Med Food. 2011 Nov;14(11):1344-51. doi: 10.1089/jmf.2010.0236. Epub 2011 Jun 11. PubMed PMID: 21663483; PubMed Central PMCID: PMC3243493.

12: Nguyen TL, Nam YS, Lee SY, Kim HC, Jang CG. Effects of capsazepine, a transient receptor potential vanilloid type 1 antagonist, on morphine-induced antinociception, tolerance, and dependence in mice. Br J Anaesth. 2010 Nov;105(5):668-74. doi: 10.1093/bja/aeq212. Epub 2010 Aug 18. PubMed PMID: 20719804.

13: Douat J, Vachon P, Beaudry F. Characterization of in vitro metabolism of capsazepine, a vanilloid transient receptor potential channel antagonist, by liquid chromatography quadrupole ion trap mass spectrometry. Biomed Chromatogr. 2011 Apr;25(4):479-92. doi: 10.1002/bmc.1471. PubMed PMID: 20586106.

14: Idris AI, Landao-Bassonga E, Ralston SH. The TRPV1 ion channel antagonist capsazepine inhibits osteoclast and osteoblast differentiation in vitro and ovariectomy induced bone loss in vivo. Bone. 2010 Apr;46(4):1089-99. doi: 10.1016/j.bone.2010.01.368. Epub 2010 Jan 22. PubMed PMID: 20096813.

15: Usmani SM, Fois G, Albrecht S, von Aulock S, Dietl P, Wittekindt OH. 2-APB and capsazepine-induced Ca2+ influx stimulates clathrin-dependent endocytosis in alveolar epithelial cells. Cell Physiol Biochem. 2010;25(1):91-102. doi: 10.1159/000272064. Epub 2009 Dec 22. PubMed PMID: 20054148.

16: Mahmmoud YA. Capsazepine, a synthetic vanilloid that converts the Na,K-ATPase to Na-ATPase. Proc Natl Acad Sci U S A. 2008 Feb 5;105(5):1757-61. doi: 10.1073/pnas.0711838105. Epub 2008 Jan 29. PubMed PMID: 18230728; PubMed Central PMCID: PMC2234217.

17: Gauden V, Hu DE, Kurokawa T, Sarker MH, Fraser PA. Novel technique for estimating cerebrovascular permeability demonstrates capsazepine protection following ischemia-reperfusion. Microcirculation. 2007 Nov-Dec;14(8):767-78. PubMed PMID: 17907014.

18: Akabori H, Yamamoto H, Tsuchihashi H, Mori T, Fujino K, Shimizu T, Endo Y, Tani T. Transient receptor potential vanilloid 1 antagonist, capsazepine, improves survival in a rat hemorrhagic shock model. Ann Surg. 2007 Jun;245(6):964-70. PubMed PMID: 17522523; PubMed Central PMCID: PMC1876964.

19: Skogvall S, Berglund M, Dalence-Guzmán MF, Svensson K, Jönsson P, Persson CG, Sterner O. Effects of capsazepine on human small airway responsiveness unravel a novel class of bronchorelaxants. Pulm Pharmacol Ther. 2007;20(3):273-80. Epub 2006 May 30. PubMed PMID: 16731017.

20: Fujimoto S, Mori M, Tsushima H, Kunimatsu M. Capsaicin-induced, capsazepine-insensitive relaxation of the guinea-pig ileum. Eur J Pharmacol. 2006 Jan 13;530(1-2):144-51. Epub 2005 Dec 19. PubMed PMID: 16360146.