SR144528 | CAS#192703-06-3 | CB2 Receptor Agonist

MedKoo Cat#: 532777 | Name: SR144528

Description:

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

SR144528 is a selective peripheral cannabinoid (CB2) receptor inverse agonist.

Chemical Structure

SR144528

CAS#192703-06-3

Theoretical Analysis

MedKoo Cat#: 532777

Name: SR144528

CAS#: 192703-06-3

Chemical Formula: C29H34ClN3O

Exact Mass: 475.2390

Molecular Weight: 476.06

Elemental Analysis: C, 73.17; H, 7.20; Cl, 7.45; N, 8.83; O, 3.36

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 1,950.00	2 Weeks
500mg	USD 3,250.00	2 Weeks
1g	USD 5,450.00	2 Weeks
2g	USD 8,950.00	2 Weeks

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Related CAS #

192703-06-3

Synonym

SR144528; SR 144528; SR-144528.

IUPAC/Chemical Name

5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-N-[(1S,4R,6S)-1,5,5-trimethyl-6-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide

InChi Key

SUGVYNSRNKFXQM-XRHWURSXSA-N

InChi Code

InChI=1S/C29H34ClN3O/c1-18-6-8-20(9-7-18)17-33-25(21-10-11-23(30)19(2)14-21)15-24(32-33)26(34)31-27-28(3,4)22-12-13-29(27,5)16-22/h6-11,14-15,22,27H,12-13,16-17H2,1-5H3,(H,31,34)/t22-,27-,29+/m1/s1

SMILES Code

O=C(C1=NN(CC2=CC=C(C)C=C2)C(C3=CC=C(Cl)C(C)=C3)=C1)N[C@@H]4C(C)(C)[C@]5([H])CC[C@@]4(C)C5

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:

SR144528 displays a Ki value of 0.6 nM for rat spleen and human recombinant CB2 receptors and a Ki value of 400 nM for rat brain and human recombinant CB1 receptors. SR144528 antagonizes the inhibitory effects of CP 55,940 on forskolin-induced adenylyl cyclase activity in CHO cells expressing hCB2 (IC50 = 10 nM) but not in cells expressing hCB1 (IC50 >10 µM).

In vitro activity:

SR144528 has potential to be a powerful tool to investigate cannabinoid system functions in the immune response. In vitro, it selectively antagonizes CP 55,940 effects on adenylyl cyclase and mitogen-activated protein kinase activity in cells expressing the h CB2 receptor, with EC50 and IC50 values of 10 nM and 39 nM, respectively. It also blocks CP 55,940-induced B-cell activation with an IC50 of 20 nM. Reference: J Pharmacol Exp Ther. 1998 Feb;284(2):644-50. https://pubmed.ncbi.nlm.nih.gov/9454810/

In vivo activity:

CB2 deletion may trigger adaptive mechanisms that reduce microglial responsiveness to inflammation. SR144528 had minimal impact on microglial activation induced by inflammatory stimulation at low concentrations in CB2-/- mice. While it suppressed activation at higher concentrations, this effect was not CB2-dependent and exceeded CB2 receptor affinity significantly. Thus, SR144528 does not replicate the anti-inflammatory effects seen in CB2 knockout microglia. Reference: Sci Rep. 2023 Jul 10;13(1):11105. https://pubmed.ncbi.nlm.nih.gov/37429837/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	63.02
	DMSO	20.0	42.01
	Ethanol	30.0	63.02

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 476.06 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. Portier M, Rinaldi-Carmona M, Pecceu F, Combes T, Poinot-Chazel C, Calandra B, Barth F, le Fur G, Casellas P. SR 144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist. J Pharmacol Exp Ther. 1999 Feb;288(2):582-9. PMID: 9918562. 2. Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, Oustric D, Sarran M, Bouaboula M, Calandra B, Portier M, Shire D, Brelière JC, Le Fur GL. SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J Pharmacol Exp Ther. 1998 Feb;284(2):644-50. PMID: 9454810. 3. Kwon EK, Choi Y, Sim S, Ye YM, Shin YS, Park HS, Ban GY. Cannabinoid receptor 2 as a regulator of inflammation induced by oleoylethanolamide in eosinophilic asthma. J Allergy Clin Immunol. 2023 Dec 5:S0091-6749(23)02406-5. doi: 10.1016/j.jaci.2023.09.043. Epub ahead of print. PMID: 38061443. 4. Olabiyi BF, Schmoele AC, Beins EC, Zimmer A. Pharmacological blockade of cannabinoid receptor 2 signaling does not affect LPS/IFN-γ-induced microglial activation. Sci Rep. 2023 Jul 10;13(1):11105. doi: 10.1038/s41598-023-37702-z. Erratum in: Sci Rep. 2023 Sep 21;13(1):15699. PMID: 37429837; PMCID: PMC10333177.

In vitro protocol:

In vivo protocol:

1. Kwon EK, Choi Y, Sim S, Ye YM, Shin YS, Park HS, Ban GY. Cannabinoid receptor 2 as a regulator of inflammation induced by oleoylethanolamide in eosinophilic asthma. J Allergy Clin Immunol. 2023 Dec 5:S0091-6749(23)02406-5. doi: 10.1016/j.jaci.2023.09.043. Epub ahead of print. PMID: 38061443. 2. Olabiyi BF, Schmoele AC, Beins EC, Zimmer A. Pharmacological blockade of cannabinoid receptor 2 signaling does not affect LPS/IFN-γ-induced microglial activation. Sci Rep. 2023 Jul 10;13(1):11105. doi: 10.1038/s41598-023-37702-z. Erratum in: Sci Rep. 2023 Sep 21;13(1):15699. PMID: 37429837; PMCID: PMC10333177.

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PMID: 38061443. 4: Trevizani M, Leal LL, Rettore JVP, Macedo GC, Alves CCS, Castro SBR, Carmo AMRD, Silva SAD, Maranduba CMDC, Silva FS. Tumor necrosis factor α, and agonist and antagonists of cannabinoid receptor type 1 and type 2 alter the immunophenotype of stem cells from human exfoliated deciduous teeth. Einstein (Sao Paulo). 2023 Nov 13;21:eAO0405. doi: 10.31744/einstein_journal/2023AO0405. PMID: 37970951; PMCID: PMC10631756. 5: Agnes JP, Dos Santos B, das Neves RN, Luciano VMM, Benvenutti L, Goldoni FC, Schran RG, Santin JR, Quintão NLM, Zanotto-Filho A. β-Caryophyllene Inhibits Oxaliplatin-Induced Peripheral Neuropathy in Mice: Role of Cannabinoid Type 2 Receptors, Oxidative Stress and Neuroinflammation. Antioxidants (Basel). 2023 Oct 22;12(10):1893. doi: 10.3390/antiox12101893. PMID: 37891972; PMCID: PMC10604080. 6: Zhao FZ, Gu WJ, Li LZ, Qu ZK, Xu MY, Liu K, Zhang F, Liu H, Xu J, Yin HY. Cannabinoid receptor 2 alleviates sepsis-associated acute lung injury by modulating maturation of dendritic cells. Int Immunopharmacol. 2023 Oct;123:110771. doi: 10.1016/j.intimp.2023.110771. Epub 2023 Aug 13. PMID: 37582314. 7: Olabiyi BF, Schmoele AC, Beins EC, Zimmer A. Pharmacological blockade of cannabinoid receptor 2 signaling does not affect LPS/IFN-γ-induced microglial activation. Sci Rep. 2023 Jul 10;13(1):11105. doi: 10.1038/s41598-023-37702-z. Erratum in: Sci Rep. 2023 Sep 21;13(1):15699. doi: 10.1038/s41598-023-42771-1. PMID: 37429837; PMCID: PMC10333177. 8: Karelia D, Corey Z, Wang H, Raup-Konsavage WM, Vrana KE, Lü J, Jiang C. Library Screening and Preliminary Characterization of Synthetic Cannabinoids Against Prostate and Pancreatic Cancer Cell Lines. Cannabis Cannabinoid Res. 2024 Apr;9(2):523-536. doi: 10.1089/can.2022.0270. Epub 2023 Mar 7. PMID: 36880938. 9: Ramsay S, Spencer NJ, Zagorodnyuk V. Endocannabinoids, anandamide and 2-AG, regulate mechanosensitivity of mucosal afferents in the Guinea pig bladder. Eur J Pharmacol. 2023 Apr 15;945:175624. doi: 10.1016/j.ejphar.2023.175624. Epub 2023 Feb 27. PMID: 36858341. 10: Cai SL, Fan XG, Wu J, Wang Y, Hu XW, Pei SY, Zheng YX, Chen J, Huang Y, Li N, Huang ZB. CB2R agonist GW405833 alleviates acute liver failure in mice via inhibiting HIF-1α-mediated reprogramming of glycometabolism and macrophage proliferation. Acta Pharmacol Sin. 2023 Jul;44(7):1391-1403. doi: 10.1038/s41401-022-01037-8. Epub 2023 Jan 25. PMID: 36697976; PMCID: PMC10310807. 11: Nagre N, Nicholson G, Cong X, Lockett J, Pearson AC, Chan V, Kim WK, Vinod KY, Catravas JD. Activation of cannabinoid-2 receptor protects against Pseudomonas aeruginosa induced acute lung injury and inflammation. Respir Res. 2022 Dec 3;23(1):326. doi: 10.1186/s12931-022-02253-w. PMID: 36463179; PMCID: PMC9719649. 12: Signorello MG, Ravera S, Leoncini G. 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Cannabidiol Improves Random-Pattern Skin Flap Survival in Rats: Involvement of Cannabinoid Type-2 Receptors. J Reconstr Microsurg. 2023 Jan;39(1):48-58. doi: 10.1055/s-0042-1749338. Epub 2022 Jul 11. PMID: 35817049. 19: El-Maadawy WH, Hafiz E, Okasha H, Osman NA, Ali GH, Hussein RA. Phycocyanin stimulates ulcerative colitis healing via selective activation of cannabinoid receptor-2, intestinal mucosal healing, Treg accumulation, and p38MAPK/MK2 signaling inhibition. Life Sci. 2022 Sep 15;305:120741. doi: 10.1016/j.lfs.2022.120741. Epub 2022 Jun 28. PMID: 35777583. 20: Capozzi A, Caissutti D, Mattei V, Gado F, Martellucci S, Longo A, Recalchi S, Manganelli V, Riitano G, Garofalo T, Sorice M, Manera C, Misasi R. Anti- Inflammatory Activity of a CB2 Selective Cannabinoid Receptor Agonist: Signaling and Cytokines Release in Blood Mononuclear Cells. Molecules. 2021 Dec 23;27(1):64. doi: 10.3390/molecules27010064. PMID: 35011295; PMCID: PMC8746368.