JNJ-17203212 | CAS#821768-06-3 | TRPV1 antagonist

JNJ-17203212
featured

WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525309

CAS#: 821768-06-3

Description: JNJ-17203212 is a reversible, competitive and potent TRPV1 antagonist (pKi values are 6.5, 7.1 and 7.3 at rat, guinea pig and human TRPV1 respectively). It inhibits capsaicin- and H+-induced channel activation (pIC50 values are 6.32 and 7.23 respectively) and exhibits antitussive and analgesic activity in vivo.

Chemical Structure

JNJ-17203212

CAS# 821768-06-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525309
Name: JNJ-17203212
CAS#: 821768-06-3
Chemical Formula: C17H15F6N5O
Exact Mass: 419.12
Molecular Weight: 419.331
Elemental Analysis: C, 48.69; H, 3.61; F, 27.18; N, 16.70; O, 3.82

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: JNJ-17203212; JNJ 17203212; JNJ17203212.

IUPAC/Chemical Name: 1-Piperazinecarboxamide, 4-(3-(trifluoromethyl)-2-pyridinyl)-N-(5-(trifluoromethyl)-2-pyridinyl)-

InChi Key: JFRYYGVYCWYIDQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H15F6N5O/c18-16(19,20)11-3-4-13(25-10-11)26-15(29)28-8-6-27(7-9-28)14-12(17(21,22)23)2-1-5-24-14/h1-5,10H,6-9H2,(H,25,26,29)

SMILES Code: O=C(N1CCN(C2=NC=CC=C2C(F)(F)F)CC1)NC3=NC=C(C(F)(F)F)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

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	JNJ-17203212 is a selective, potent and competitive TRPV1 antagonist.
In vitro activity:	Fig. 2B shows that 500 nm JNJ-17203212 was very effective in inhibiting 20 nm capsaicin-induced Ca2+ increases in TRPV1-expressing HEK cells, whereas Fig. 2C demonstrates that the same concentration of JNJ-17203212 completely inhibited 10 μm imperatorin-induced responses. Reference: J Biol Chem. 2014 Apr 4;289(14):9600-10. https://pubmed.ncbi.nlm.nih.gov/24569998/
In vivo activity:	Inflammatory up-regulation of c-fos in the rat trigeminal brain stem complex was dose-dependently and significantly reduced by both TRPV1 antagonists. JNJ-17203212 was effective in all doses and fully abolished CGRP release in a time and dose-dependent manner. Reference: J Headache Pain. 2015;16:57. https://pubmed.ncbi.nlm.nih.gov/26109436/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	71.54
	DMSO	57.3	136.67
	Ethanol	24.0	57.18

Preparing Stock Solutions

The following data is based on the product molecular weight 419.33 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.

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

Formulation protocol:	1. Chen X, Sun W, Gianaris NG, Riley AM, Cummins TR, Fehrenbacher JC, Obukhov AG. Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel. J Biol Chem. 2014 Apr 4;289(14):9600-10. doi: 10.1074/jbc.M113.536862. Epub 2014 Feb 25. PMID: 24569998; PMCID: PMC3975010. 2. Meents JE, Hoffmann J, Chaplan SR, Neeb L, Schuh-Hofer S, Wickenden A, Reuter U. Two TRPV1 receptor antagonists are effective in two different experimental models of migraine. J Headache Pain. 2015;16:57. doi: 10.1186/s10194-015-0539-z. Epub 2015 Jun 24. PMID: 26109436; PMCID: PMC4491068. 3. Bhattacharya A, Scott BP, Nasser N, Ao H, Maher MP, Dubin AE, Swanson DM, Shankley NP, Wickenden AD, Chaplan SR. Pharmacology and antitussive efficacy of 4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid (5-trifluoromethyl-pyridin-2-yl)-amide (JNJ17203212), a transient receptor potential vanilloid 1 antagonist in guinea pigs. J Pharmacol Exp Ther. 2007 Nov;323(2):665-74. doi: 10.1124/jpet.107.127258. Epub 2007 Aug 9. PMID: 17690251.
In vitro protocol:	1. Chen X, Sun W, Gianaris NG, Riley AM, Cummins TR, Fehrenbacher JC, Obukhov AG. Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel. J Biol Chem. 2014 Apr 4;289(14):9600-10. doi: 10.1074/jbc.M113.536862. Epub 2014 Feb 25. PMID: 24569998; PMCID: PMC3975010.
In vivo protocol:	1. Meents JE, Hoffmann J, Chaplan SR, Neeb L, Schuh-Hofer S, Wickenden A, Reuter U. Two TRPV1 receptor antagonists are effective in two different experimental models of migraine. J Headache Pain. 2015;16:57. doi: 10.1186/s10194-015-0539-z. Epub 2015 Jun 24. PMID: 26109436; PMCID: PMC4491068. 2. Bhattacharya A, Scott BP, Nasser N, Ao H, Maher MP, Dubin AE, Swanson DM, Shankley NP, Wickenden AD, Chaplan SR. Pharmacology and antitussive efficacy of 4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid (5-trifluoromethyl-pyridin-2-yl)-amide (JNJ17203212), a transient receptor potential vanilloid 1 antagonist in guinea pigs. J Pharmacol Exp Ther. 2007 Nov;323(2):665-74. doi: 10.1124/jpet.107.127258. Epub 2007 Aug 9. PMID: 17690251.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Meents JE, Hoffmann J, Chaplan SR, Neeb L, Schuh-Hofer S, Wickenden A, Reuter U. Two TRPV1 receptor antagonists are effective in two different experimental models of migraine. J Headache Pain. 2015;16:57. doi: 10.1186/s10194-015-0539-z. Epub 2015 Jun 24. PubMed PMID: 26109436; PubMed Central PMCID: PMC4491068.

2: Ono K, Ye Y, Viet CT, Dang D, Schmidt BL. TRPV1 expression level in isolectin B₄-positive neurons contributes to mouse strain difference in cutaneous thermal nociceptive sensitivity. J Neurophysiol. 2015 May 1;113(9):3345-55. doi: 10.1152/jn.00973.2014. Epub 2015 Mar 18. PubMed PMID: 25787958; PubMed Central PMCID: PMC4443607.

3: Chen X, Sun W, Gianaris NG, Riley AM, Cummins TR, Fehrenbacher JC, Obukhov AG. Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel. J Biol Chem. 2014 Apr 4;289(14):9600-10. doi: 10.1074/jbc.M113.536862. Epub 2014 Feb 25. PubMed PMID: 24569998; PubMed Central PMCID: PMC3975010.

4: Ye Y, Bae SS, Viet CT, Troob S, Bernabé D, Schmidt BL. IB4(+) and TRPV1(+) sensory neurons mediate pain but not proliferation in a mouse model of squamous cell carcinoma. Behav Brain Funct. 2014 Feb 13;10:5. doi: 10.1186/1744-9081-10-5. PubMed PMID: 24524628; PubMed Central PMCID: PMC3942073.

5: Kelly S, Chapman RJ, Woodhams S, Sagar DR, Turner J, Burston JJ, Bullock C, Paton K, Huang J, Wong A, McWilliams DF, Okine BN, Barrett DA, Hathway GJ, Walsh DA, Chapman V. Increased function of pronociceptive TRPV1 at the level of the joint in a rat model of osteoarthritis pain. Ann Rheum Dis. 2015 Jan;74(1):252-9. doi: 10.1136/annrheumdis-2013-203413. Epub 2013 Oct 23. PubMed PMID: 24152419; PubMed Central PMCID: PMC4283626.

6: Ma J, Altomare A, Guarino M, Cicala M, Rieder F, Fiocchi C, Li D, Cao W, Behar J, Biancani P, Harnett KM. HCl-induced and ATP-dependent upregulation of TRPV1 receptor expression and cytokine production by human esophageal epithelial cells. Am J Physiol Gastrointest Liver Physiol. 2012 Sep 1;303(5):G635-45. doi: 10.1152/ajpgi.00097.2012. Epub 2012 Jul 12. PubMed PMID: 22790593; PubMed Central PMCID: PMC3468560.

7: Raemdonck K, de Alba J, Birrell MA, Grace M, Maher SA, Irvin CG, Fozard JR, O'Byrne PM, Belvisi MG. A role for sensory nerves in the late asthmatic response. Thorax. 2012 Jan;67(1):19-25. doi: 10.1136/thoraxjnl-2011-200365. Epub 2011 Aug 13. PubMed PMID: 21841185.

8: Huang SM, Li X, Yu Y, Wang J, Caterina MJ. TRPV3 and TRPV4 ion channels are not major contributors to mouse heat sensation. Mol Pain. 2011 May 17;7:37. doi: 10.1186/1744-8069-7-37. PubMed PMID: 21586160; PubMed Central PMCID: PMC3123222.

9: Wiskur BJ, Tyler K, Campbell-Dittmeyer K, Chaplan SR, Wickenden AD, Greenwood-Van Meerveld B. A novel TRPV1 receptor antagonist JNJ-17203212 attenuates colonic hypersensitivity in rats. Methods Find Exp Clin Pharmacol. 2010 Oct;32(8):557-64. doi: 10.1358/mf.2010.32.8.1507853. PubMed PMID: 21132125.

10: Cefalu JS, Guillon MA, Burbach LR, Zhu QM, Hu DQ, Ho MJ, Ford AP, Nunn PA, Cockayne DA. Selective pharmacological blockade of the TRPV1 receptor suppresses sensory reflexes of the rodent bladder. J Urol. 2009 Aug;182(2):776-85. doi: 10.1016/j.juro.2009.03.085. Epub 2009 Jun 18. PubMed PMID: 19539322.

11: Huang SM, Lee H, Chung MK, Park U, Yu YY, Bradshaw HB, Coulombe PA, Walker JM, Caterina MJ. Overexpressed transient receptor potential vanilloid 3 ion channels in skin keratinocytes modulate pain sensitivity via prostaglandin E2. J Neurosci. 2008 Dec 17;28(51):13727-37. doi: 10.1523/JNEUROSCI.5741-07.2008. Erratum in: J Neurosci. 2009 Jan 21;29(3):29. PubMed PMID: 19091963; PubMed Central PMCID: PMC2676929.

12: Bhattacharya A, Scott BP, Nasser N, Ao H, Maher MP, Dubin AE, Swanson DM, Shankley NP, Wickenden AD, Chaplan SR. Pharmacology and antitussive efficacy of 4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid (5-trifluoromethyl-pyridin-2-yl)-amide (JNJ17203212), a transient receptor potential vanilloid 1 antagonist in guinea pigs. J Pharmacol Exp Ther. 2007 Nov;323(2):665-74. Epub 2007 Aug 9. PubMed PMID: 17690251.

13: Swanson DM, Dubin AE, Shah C, Nasser N, Chang L, Dax SL, Jetter M, Breitenbucher JG, Liu C, Mazur C, Lord B, Gonzales L, Hoey K, Rizzolio M, Bogenstaetter M, Codd EE, Lee DH, Zhang SP, Chaplan SR, Carruthers NI. Identification and biological evaluation of 4-(3-trifluoromethylpyridin-2-yl)piperazine-1-carboxylic acid (5-trifluoromethylpyridin-2-yl)amide, a high affinity TRPV1 (VR1) vanilloid receptor antagonist. J Med Chem. 2005 Mar 24;48(6):1857-72. PubMed PMID: 15771431.

Your view history

JNJ-17203212 featured