SB 452533 | CAS# 459429-39-1 | TRPV1 antagonist

MedKoo Cat#: 532670 | Name: SB 452533

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Description:

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

SB 452533 is a potent TRPV1 antagonist against capsaicin (pKb = 7.7), noxious heat and acid-mediated (pIC50 = 7.0) receptor activation (pKi = 6.22 at the recombinant hTRPV1 receptor).

Chemical Structure

SB 452533

CAS# 459429-39-1

Theoretical Analysis

MedKoo Cat#: 532670

Name: SB 452533

CAS#: 459429-39-1

Chemical Formula: C18H22BrN3O

Exact Mass: 375.0946

Molecular Weight: 376.30

Elemental Analysis: C, 57.45; H, 5.89; Br, 21.23; N, 11.17; O, 4.25

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 345.00	2 Weeks
50mg	USD 1,135.00	2 Weeks

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Related CAS #

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Synonym

SB452533; SB 452533; SB-452533.

IUPAC/Chemical Name

1-(2-bromophenyl)-3-{2-[ethyl(3-methylphenyl)amino]ethyl}urea

InChi Key

IFJYEGJUQIBBQV-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H22BrN3O/c1-3-22(15-8-6-7-14(2)13-15)12-11-20-18(23)21-17-10-5-4-9-16(17)19/h4-10,13H,3,11-12H2,1-2H3,(H2,20,21,23)

SMILES Code

O=C(NCCN(CC)C1=CC=CC(C)=C1)NC2=CC=CC=C2Br

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

Special Conditions: No more than 500 mg per individual per year to be sold without prior permission from the license holder, GlaxoSmithKline.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SB 452533 is a potent TRPV1 antagonist against capsaicin (pKb = 7.7), noxious heat and acid-mediated (pIC50 = 7.0) receptor activation (pKi = 6.22 at the recombinant hTRPV1 receptor).

In vitro activity:

This study found that SB 452533 was an antagonist versus capsaicin, noxious heat and acid mediated activation of TRPV1. Study of a quaternary salt of SB 452533 supports a mode of action in which compounds from this series (ureas) cause inhibition via an extracellularly accessible binding site on the TRPV1 receptor. Reference: Bioorg Med Chem Lett. 2004 Jul 16;14(14):3631-4. https://pubmed.ncbi.nlm.nih.gov/15203132/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 376.30 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. Almaghrabi SY, Geraghty DP, Ahuja KD, Adams MJ. Vanilloid-like agents inhibit aggregation of human platelets. Thromb Res. 2014 Aug;134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. Epub 2014 Jun 6. PMID: 24953906. 2. Rami HK, Thompson M, Wyman P, Jerman JC, Egerton J, Brough S, Stevens AJ, Randall AD, Smart D, Gunthorpe MJ, Davis JB. Discovery of small molecule antagonists of TRPV1. Bioorg Med Chem Lett. 2004 Jul 16;14(14):3631-4. doi: 10.1016/j.bmcl.2004.05.028. PMID: 15203132.

In vitro protocol:

In vivo protocol:

To be determined

1: Vahidi Ferdowsi P, Ahuja KDK, Beckett JM, Myers S. TRPV1 Activation by Capsaicin Mediates Glucose Oxidation and ATP Production Independent of Insulin Signalling in Mouse Skeletal Muscle Cells. Cells. 2021 Jun 21;10(6):1560. doi: 10.3390/cells10061560. PMID: 34205555; PMCID: PMC8234135. 2: Lu LM, Yu TT, He XW, Tang J, Li XW. [Effect of small dose capsaicin for treatment of pulmonary fibrosis in mice and its mechanism]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2020 May;36(3):216-222. Chinese. doi: 10.12047/j.cjap.5974.2020.048. PMID: 32981275. 3: Vijayvergiya V, Acharya S, Wilson SP, Schmidt JJ. Measurement of Ensemble TRPV1 Ion Channel Currents Using Droplet Bilayers. PLoS One. 2015 Oct 29;10(10):e0141366. doi: 10.1371/journal.pone.0141366. PMID: 26513481; PMCID: PMC4626236. 4: Almaghrabi SY, Geraghty DP, Ahuja KD, Adams MJ. Vanilloid-like agents inhibit aggregation of human platelets. Thromb Res. 2014 Aug;134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. Epub 2014 Jun 6. PMID: 24953906. 5: Gunthorpe MJ, Hannan SL, Smart D, Jerman JC, Arpino S, Smith GD, Brough S, Wright J, Egerton J, Lappin SC, Holland VA, Winborn K, Thompson M, Rami HK, Randall A, Davis JB. Characterization of SB-705498, a potent and selective vanilloid receptor-1 (VR1/TRPV1) antagonist that inhibits the capsaicin-, acid-, and heat-mediated activation of the receptor. J Pharmacol Exp Ther. 2007 Jun;321(3):1183-92. doi: 10.1124/jpet.106.116657. Epub 2007 Mar 28. PMID: 17392405. 6: Rami HK, Thompson M, Stemp G, Fell S, Jerman JC, Stevens AJ, Smart D, Sargent B, Sanderson D, Randall AD, Gunthorpe MJ, Davis JB. Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3287-91. doi: 10.1016/j.bmcl.2006.03.030. Epub 2006 Mar 31. PMID: 16580202. 7: Weil A, Moore SE, Waite NJ, Randall A, Gunthorpe MJ. Conservation of functional and pharmacological properties in the distantly related temperature sensors TRVP1 and TRPM8. Mol Pharmacol. 2005 Aug;68(2):518-27. doi: 10.1124/mol.105.012146. Epub 2005 May 23. PMID: 15911692. 8: Rami HK, Thompson M, Wyman P, Jerman JC, Egerton J, Brough S, Stevens AJ, Randall AD, Smart D, Gunthorpe MJ, Davis JB. Discovery of small molecule antagonists of TRPV1. Bioorg Med Chem Lett. 2004 Jul 16;14(14):3631-4. doi: 10.1016/j.bmcl.2004.05.028. PMID: 15203132.