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MedKoo Cat#: 526818 | Name: SR3335
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Description:

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

SR3335, also known as ML 176, is a RORα selective inverse agonist. SR3335 directly binds to RORα, but not other RORs, and functions as a selective partial inverse agonist of RORα in cell-based assays. Furthermore, SR3335 suppresses the expression of endogenous RORα target genes in HepG2 involved in hepatic gluconeogenesis including glucose-6-phosphatase and phosphoenolpyruvate carboxykinase. SR3335 can be utilized as a chemical tool to probe the function of this receptor both in vitro and in vivo. SR3335 may hold utility for suppression of elevated hepatic glucose production in type 2 diabetics.

Chemical Structure

SR3335
CAS#293753-05-6

Theoretical Analysis

MedKoo Cat#: 526818

Name: SR3335

CAS#: 293753-05-6

Chemical Formula: C13H9F6NO3S2

Exact Mass: 404.9928

Molecular Weight: 405.33

Elemental Analysis: C, 38.52; H, 2.24; F, 28.12; N, 3.46; O, 11.84; S, 15.82

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 500.00 2 Weeks
25mg USD 830.00 2 Weeks
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Related CAS #
No Data
Synonym
SR3335; SR-3335; SR 3335; ML 176; ML-176; ML176.
IUPAC/Chemical Name
N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-2-thiophenesulfonamide
InChi Key
LZWUNZRMANFRAO-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H9F6NO3S2/c14-12(15,16)11(21,13(17,18)19)8-3-5-9(6-4-8)20-25(22,23)10-2-1-7-24-10/h1-7,20-21H
SMILES Code
O=S(C1=CC=CS1)(NC2=CC=C(C(C(F)(F)F)(O)C(F)(F)F)C=C2)=O
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, DMF, and ethanol
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:
SR3335 competitively inhibits the binding of 25-hydroxycholesterol to the ligand binding domain (Ki = 220 nM) and inhibits constitutive transactivation activity (IC50 = 480 nM). It is without effect on RORβ, RORγ, farnesoid X receptor, or liver X receptor α.
In vitro activity:
SR3335 is a promising drug in reversing the deleterious microenvironment in intervertebral disc degenerative disease (IDD) patients. SR3335 reversed the trend of increased apoptosis in nucleus pulposus (NP) cells induced by TNF-α treatment. Also, SR3335 mediated the effect in NP cells by regulating the YAP signaling pathway, especially by affecting the phosphorylation state of YAP. Reference: Mediators Inflamm. 2021 Jul 28;2021:9954909. https://pubmed.ncbi.nlm.nih.gov/34366712/
In vivo activity:
RORα inverse agonists such as SR3335 may hold utility for suppression of elevated hepatic glucose production in type 2 diabetics. SR3335-treated mice displayed lower plasma glucose levels following the pyruvate challenge, consistent with suppression of gluconeogenesis. Reference: ACS Chem Biol. 2011 Mar 18;6(3):218-22. https://pubmed.ncbi.nlm.nih.gov/21090593/
Solvent mg/mL mM comments
Solubility
DMF 20.0 49.34
DMSO 16.0 39.47
Ethanol 33.0 81.42
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 405.33 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.

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
Formulation protocol:
1. Liang T, Qiu J, Li S, Deng Z, Qiu X, Hu W, Li P, Chen T, Liang Z, Zhou H, Gao B, Huang D, Liang A, Gao W. Inverse Agonist of Retinoid-Related Orphan Receptor-Alpha Prevents Apoptosis and Degeneration in Nucleus Pulposus Cells via Upregulation of YAP. Mediators Inflamm. 2021 Jul 28;2021:9954909. doi: 10.1155/2021/9954909. PMID: 34366712; PMCID: PMC8337132. 2. Rajput C, Cui T, Han M, Lei J, Hinde JL, Wu Q, Bentley JK, Hershenson MB. RORα-dependent type 2 innate lymphoid cells are required and sufficient for mucous metaplasia in immature mice. Am J Physiol Lung Cell Mol Physiol. 2017 Jun 1;312(6):L983-L993. doi: 10.1152/ajplung.00368.2016. Epub 2017 Mar 30. PMID: 28360114; PMCID: PMC5495952. 3. Kumar N, Kojetin DJ, Solt LA, Kumar KG, Nuhant P, Duckett DR, Cameron MD, Butler AA, Roush WR, Griffin PR, Burris TP. Identification of SR3335 (ML-176): a synthetic RORα selective inverse agonist. ACS Chem Biol. 2011 Mar 18;6(3):218-22. doi: 10.1021/cb1002762. Epub 2010 Dec 6. PMID: 21090593; PMCID: PMC3076127.
In vitro protocol:
1. Liang T, Qiu J, Li S, Deng Z, Qiu X, Hu W, Li P, Chen T, Liang Z, Zhou H, Gao B, Huang D, Liang A, Gao W. Inverse Agonist of Retinoid-Related Orphan Receptor-Alpha Prevents Apoptosis and Degeneration in Nucleus Pulposus Cells via Upregulation of YAP. Mediators Inflamm. 2021 Jul 28;2021:9954909. doi: 10.1155/2021/9954909. PMID: 34366712; PMCID: PMC8337132.
In vivo protocol:
1. Rajput C, Cui T, Han M, Lei J, Hinde JL, Wu Q, Bentley JK, Hershenson MB. RORα-dependent type 2 innate lymphoid cells are required and sufficient for mucous metaplasia in immature mice. Am J Physiol Lung Cell Mol Physiol. 2017 Jun 1;312(6):L983-L993. doi: 10.1152/ajplung.00368.2016. Epub 2017 Mar 30. PMID: 28360114; PMCID: PMC5495952. 2. Kumar N, Kojetin DJ, Solt LA, Kumar KG, Nuhant P, Duckett DR, Cameron MD, Butler AA, Roush WR, Griffin PR, Burris TP. Identification of SR3335 (ML-176): a synthetic RORα selective inverse agonist. ACS Chem Biol. 2011 Mar 18;6(3):218-22. doi: 10.1021/cb1002762. Epub 2010 Dec 6. PMID: 21090593; PMCID: PMC3076127.
1: Chen D, Mo F, Liu M, Liu L, Xing J, Xiao W, Gong Y, Tang S, Tan Z, Liang G, Xie H, Huang J, Shen J, Pan X. Characteristics of splenic PD-1+ γδT cells in Plasmodium yoelii nigeriensis infection. Immunol Res. 2024 Jun;72(3):383-394. doi: 10.1007/s12026-023-09441-w. Epub 2024 Jan 24. Erratum in: Immunol Res. 2024 Jun;72(3):395. doi: 10.1007/s12026-024-09469-6. PMID: 38265549; PMCID: PMC11217126. 2: Xiong J, Wang Z, Dong Y, Cao J, Chen Y. The signal pathway of melatonin mediates the monochromatic light-induced T-lymphocyte apoptosis in chicken thymus. Poult Sci. 2024 Feb;103(2):103331. doi: 10.1016/j.psj.2023.103331. Epub 2023 Nov 29. PMID: 38100948; PMCID: PMC10764265. 3: Zhang Y, Wang Z, Dong Y, Cao J, Chen Y. Melatonin Nuclear Receptors Mediate Green-and-Blue-Monochromatic-Light-Combinations-Inhibited B Lymphocyte Apoptosis in the Bursa of Chickens via Reducing Oxidative Stress and Nfκb Expression. Antioxidants (Basel). 2022 Apr 8;11(4):748. doi: 10.3390/antiox11040748. PMID: 35453433; PMCID: PMC9029876. 4: Liang T, Qiu J, Li S, Deng Z, Qiu X, Hu W, Li P, Chen T, Liang Z, Zhou H, Gao B, Huang D, Liang A, Gao W. Inverse Agonist of Retinoid-Related Orphan Receptor- Alpha Prevents Apoptosis and Degeneration in Nucleus Pulposus Cells via Upregulation of YAP. Mediators Inflamm. 2021 Jul 28;2021:9954909. doi: 10.1155/2021/9954909. PMID: 34366712; PMCID: PMC8337132. 5: Wahyuni T, Kobayashi A, Tanaka S, Miyake Y, Yamamoto A, Bahtiar A, Mori S, Kametani Y, Tomimatsu M, Matsumoto K, Maeda M, Obana M, Fujio Y. Maresin-1 induces cardiomyocyte hypertrophy through IGF-1 paracrine pathway. Am J Physiol Cell Physiol. 2021 Jul 1;321(1):C82-C93. doi: 10.1152/ajpcell.00568.2020. Epub 2021 May 26. PMID: 34038245. 6: Auclair M, Roblot N, Capel E, Fève B, Antoine B. Pharmacological modulation of RORα controls fat browning, adaptive thermogenesis, and body weight in mice. Am J Physiol Endocrinol Metab. 2021 Feb 1;320(2):E219-E233. doi: 10.1152/ajpendo.00131.2020. Epub 2020 Nov 30. PMID: 33252251; PMCID: PMC8260366. 7: Xiong J, Wang Z, Cao J, Dong Y, Chen Y. Melatonin mediates monochromatic light-induced proliferation of T/B lymphocytes in the spleen via the membrane receptor or nuclear receptor. Poult Sci. 2020 Sep;99(9):4294-4302. doi: 10.1016/j.psj.2020.06.008. Epub 2020 Jun 24. PMID: 32867973; PMCID: PMC7598018. 8: Ito I, Bhopale KK, Kobayashi M, Finnerty CC, Herndon DN, Suzuki F. Lamina propria group 2 innate lymphoid cells impair the antibacterial defense of burned mice to enterococcal translocation. J Leukoc Biol. 2017 Dec;102(6):1451-1460. doi: 10.1189/jlb.4A0517-195R. Epub 2017 Sep 26. PMID: 28951418. 9: Rajput C, Cui T, Han M, Lei J, Hinde JL, Wu Q, Bentley JK, Hershenson MB. RORα-dependent type 2 innate lymphoid cells are required and sufficient for mucous metaplasia in immature mice. Am J Physiol Lung Cell Mol Physiol. 2017 Jun 1;312(6):L983-L993. doi: 10.1152/ajplung.00368.2016. Epub 2017 Mar 30. PMID: 28360114; PMCID: PMC5495952. 10: Zhao Y, Xu L, Ding S, Lin N, Ji Q, Gao L, Su Y, He B, Pu J. Novel protective role of the circadian nuclear receptor retinoic acid-related orphan receptor-α in diabetic cardiomyopathy. J Pineal Res. 2017 Apr;62(3). doi: 10.1111/jpi.12378. Epub 2017 Feb 22. PMID: 27862268. 11: Kumar N, Nuhant P, Solt LA, Conkright JJ, Wang Y, Istrate MA, Busby SA, Ruben DGO, Burris TP, Cameron M, Mercer BA, Hodder P, Roush WR, Rosen H, Griffin PR. Identification of a novel selective inverse agonist probe and analogs for the Retinoic acid receptor-related Orphan Receptor Alpha (RORα). 2010 Sep 1 [updated 2013 Mar 14]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23762959. 12: Kumar N, Kojetin DJ, Solt LA, Kumar KG, Nuhant P, Duckett DR, Cameron MD, Butler AA, Roush WR, Griffin PR, Burris TP. Identification of SR3335 (ML-176): a synthetic RORα selective inverse agonist. ACS Chem Biol. 2011 Mar 18;6(3):218-22. doi: 10.1021/cb1002762. Epub 2010 Dec 6. PMID: 21090593; PMCID: PMC3076127.