SQ-29548 | CAS#98672-91-4 | TP receptor antagonist

MedKoo Cat#: 532769 | Name: SQ-29548

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Description:

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

SQ-29548 is a highly selective TP receptor antagonist which binds to the human recombinant TP receptor with a Ki of 4.1 nM. SQ-29548 inhibits the aggregation of washed human platelets induced by U-46619 with an IC50 of 0.06 µM.

Chemical Structure

SQ-29548

CAS#98672-91-4

Theoretical Analysis

MedKoo Cat#: 532769

Name: SQ-29548

CAS#: 98672-91-4

Chemical Formula: C21H29N3O4

Exact Mass: 387.2158

Molecular Weight: 387.48

Elemental Analysis: C, 65.10; H, 7.54; N, 10.84; O, 16.52

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 600.00	2 weeks
10mg	USD 1,050.00	2 weeks

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Related CAS #

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Synonym

SQ-29548; SQ 29548; SQ29548.

IUPAC/Chemical Name

(Z)-7-[(1R,4S,5R,6R)-5-[(2-(phenylcarbamoyl)hydrazinyl)methyl]-7-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid

InChi Key

RJNDVCNWVBWHLY-OQMICVBCSA-N

InChi Code

InChI=1S/C21H29N3O4/c25-20(26)11-7-2-1-6-10-16-17(19-13-12-18(16)28-19)14-22-24-21(27)23-15-8-4-3-5-9-15/h1,3-6,8-9,16-19,22H,2,7,10-14H2,(H,25,26)(H2,23,24,27)/b6-1-/t16-,17+,18-,19+/m1/s1

SMILES Code

O=C(O)CCC/C=C\C[C@@H]1[C@H](CNNC(NC2=CC=CC=C2)=O)[C@]3([H])CC[C@@]1([H])O3

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:

SQ-29548 binds to the human recombinant TP receptor with a Ki of 4.1 nM. It inhibits the aggregation of washed human platelets induced by U-46619 with an IC50 of 0.06 µM.

In vitro activity:

SQ-29548 has potential neuroprotective properties. SQ-29548 improved the antioxidant capacities of SH‑SY5Y cells and reduced the cell apoptosis through the inhibition of MAPK pathways. Pretreatment with SQ-29548 not only rescued the viability of SH‑SY5Y cells, but also ameliorated the intracellular ROS level and the expression levels of SOD2 and catalase. Reference: Int J Mol Med. 2018 Jul;42(1):479-488. https://pubmed.ncbi.nlm.nih.gov/29620149/

In vivo activity:

TXA2 receptors (TP) antagonists like SQ-29548 could be beneficial in treating seizure-induced damage. SQ-29548 administration after pilocarpine-induced seizures in adult C57BL/6 mice improved neuromotor performance and reduced neurodegeneration, astrocytosis, and c-Fos protein levels in the hippocampus. Some animals responded positively to SQ-29548 treatment; however, 4 out of 12 SQ-29548-treated animals did not show improvement and were considered to be SQ-29548 non-responders. Reference: Epilepsy Res. 2020 Feb;160:106277. https://pubmed.ncbi.nlm.nih.gov/32036236/

	Solvent	mg/mL	mM
Solubility
	DMF	0.2	0.52
	DMSO	5.0	12.90
	Ethanol	0.5	1.29

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 387.48 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. Cai G, Yan A, Fu N, Fu Y. Thromboxane A2 receptor antagonist SQ29548 attenuates SH‑SY5Y neuroblastoma cell impairments induced by oxidative stress. Int J Mol Med. 2018 Jul;42(1):479-488. doi: 10.3892/ijmm.2018.3589. Epub 2018 Mar 27. PMID: 29620149. 2. Liu Q, Tao B, Liu G, Chen G, Zhu Q, Yu Y, Yu Y, Xiong H. Thromboxane A2 Receptor Inhibition Suppresses Multiple Myeloma Cell Proliferation by Inducing p38/c-Jun N-terminal Kinase (JNK) Mitogen-activated Protein Kinase (MAPK)-mediated G2/M Progression Delay and Cell Apoptosis. J Biol Chem. 2016 Feb 26;291(9):4779-92. doi: 10.1074/jbc.M115.683052. Epub 2016 Jan 2. PMID: 26724804; PMCID: PMC4813499. 3. Mello FK, Freitas ML, Souto NS, Zorzi VN, Moreira MP, Neuberger B, Costa KG, Fighera MR, Royes LF, Furian AF, Oliveira MS. Neuroprotective effects of thromboxane receptor antagonist SQ 29,548 after pilocarpine-induced status epilepticus in mice. Epilepsy Res. 2020 Feb;160:106277. doi: 10.1016/j.eplepsyres.2020.106277. Epub 2020 Jan 16. PMID: 32036236. 4. Yan A, Zhang T, Yang X, Shao J, Fu N, Shen F, Fu Y, Xia W. Thromboxane A2 receptor antagonist SQ29548 reduces ischemic stroke-induced microglia/macrophages activation and enrichment, and ameliorates brain injury. Sci Rep. 2016 Oct 24;6:35885. doi: 10.1038/srep35885. PMID: 27775054; PMCID: PMC5075919.

In vitro protocol:

In vivo protocol:

1. Mello FK, Freitas ML, Souto NS, Zorzi VN, Moreira MP, Neuberger B, Costa KG, Fighera MR, Royes LF, Furian AF, Oliveira MS. Neuroprotective effects of thromboxane receptor antagonist SQ 29,548 after pilocarpine-induced status epilepticus in mice. Epilepsy Res. 2020 Feb;160:106277. doi: 10.1016/j.eplepsyres.2020.106277. Epub 2020 Jan 16. PMID: 32036236. 2. Yan A, Zhang T, Yang X, Shao J, Fu N, Shen F, Fu Y, Xia W. Thromboxane A2 receptor antagonist SQ29548 reduces ischemic stroke-induced microglia/macrophages activation and enrichment, and ameliorates brain injury. Sci Rep. 2016 Oct 24;6:35885. doi: 10.1038/srep35885. PMID: 27775054; PMCID: PMC5075919.

1: Halvorson BD, Bao Y, Singh KK, Frisbee SJ, Hachinski V, Whitehead SN, Melling CWJ, Chantler PD, Goldman D, Frisbee JC. Thromboxane-induced cerebral microvascular rarefaction predicts depressive symptom emergence in metabolic disease. J Appl Physiol (1985). 2024 Jan 1;136(1):122-140. doi: 10.1152/japplphysiol.00410.2023. Epub 2023 Nov 16. PMID: 37969083. 2: Prakash E, Pavithra S, Kishor Kumar DG, Panigrahi M, Singh TU, Kumar D, Parida S. TXA2 mediates LPA1-stimulated uterine contraction in late pregnant mouse. Prostaglandins Other Lipid Mediat. 2023 Aug;167:106736. doi: 10.1016/j.prostaglandins.2023.106736. Epub 2023 Apr 14. PMID: 37062326. 3: Molnár PJ, Dér B, Borsodi K, Balla H, Borbás Z, Molnár K, Ruisanchez É, Kenessey I, Horváth A, Keszthelyi A, Majoros A, Nyirády P, Offermanns S, Benyó Z. Isoprostanes evoke contraction of the murine and human detrusor muscle via activation of the thromboxane prostanoid TP receptor and Rho kinase. Am J Physiol Renal Physiol. 2021 Apr 1;320(4):F537-F547. doi: 10.1152/ajprenal.00400.2020. Epub 2021 Jan 25. PMID: 33491563. 4: Majewski M, Kucharczyk E, Kaliszan R, Markuszewski M, Fotschki B, Juśkiewicz J, Borkowska-Sztachańska M, Ognik K. The Characterization of Ground Raspberry Seeds and the Physiological Response to Supplementation in Hypertensive and Normotensive Rats. Nutrients. 2020 Jun 1;12(6):1630. doi: 10.3390/nu12061630. PMID: 32492905; PMCID: PMC7352221. 5: Chen H, Simonsen U, Aalkjaer C. A sex-specific, COX-derived/thromboxane receptor activator causes depolarization and vasoconstriction in male mice mesenteric resistance arteries. Basic Clin Pharmacol Toxicol. 2020 Aug;127(2):152-159. doi: 10.1111/bcpt.13413. Epub 2020 May 4. PMID: 32291865. 6: Mello FK, Freitas ML, Souto NS, Zorzi VN, Moreira MP, Neuberger B, Costa KG, Fighera MR, Royes LF, Furian AF, Oliveira MS. Neuroprotective effects of thromboxane receptor antagonist SQ 29,548 after pilocarpine-induced status epilepticus in mice. Epilepsy Res. 2020 Feb;160:106277. doi: 10.1016/j.eplepsyres.2020.106277. Epub 2020 Jan 16. PMID: 32036236. 7: Lawandy I, Liu Y, Shi G, Zhang Z, Scrimgeour LA, Pavlov V, Jaworski R, Sellke FW, Feng J. Increased coronary arteriolar contraction to serotonin in juvenile pigs with metabolic syndrome. Mol Cell Biochem. 2019 Nov;461(1-2):57-64. doi: 10.1007/s11010-019-03589-6. Epub 2019 Jul 27. PMID: 31352610; PMCID: PMC6790190. 8: Frisbee JC, Lewis MT, Kasper JD, Chantler PD, Wiseman RW. Type 2 diabetes mellitus in the Goto-Kakizaki rat impairs microvascular function and contributes to premature skeletal muscle fatigue. J Appl Physiol (1985). 2019 Mar 1;126(3):626-637. doi: 10.1152/japplphysiol.00751.2018. Epub 2018 Dec 20. PMID: 30571284; PMCID: PMC6459383. 9: Freitas ML, Mello FK, Souza TL, Grauncke ACB, Fighera MR, Royes LFF, Furian AF, Oliveira MS. Anticonvulsant-like effect of thromboxane receptor agonist U-46619 against pentylenetetrazol-induced seizures. Epilepsy Res. 2018 Oct;146:137-143. doi: 10.1016/j.eplepsyres.2018.08.003. Epub 2018 Aug 20. PMID: 30153647. 10: Xu H, Lu H, Zhu X, Wang W, Zhang Z, Fu H, Ma S, Luo Y, Fu J. Inhibitory effects of luteolin‑4'‑O‑β‑D‑glucopyranoside on P2Y12 and thromboxane A2 receptor‑mediated amplification of platelet activation in vitro. Int J Mol Med. 2018 Jul;42(1):615-624. doi: 10.3892/ijmm.2018.3634. Epub 2018 Apr 19. PMID: 29693158. 11: Cai G, Yan A, Fu N, Fu Y. Thromboxane A2 receptor antagonist SQ29548 attenuates SH‑SY5Y neuroblastoma cell impairments induced by oxidative stress. Int J Mol Med. 2018 Jul;42(1):479-488. doi: 10.3892/ijmm.2018.3589. Epub 2018 Mar 27. PMID: 29620149. 12: García-Redondo AB, Esteban V, Briones AM, Díaz Del Campo LS, González-Amor M, Méndez-Barbero N, Campanero MR, Redondo JM, Salaices M. Regulator of calcineurin 1 modulates vascular contractility and stiffness through the upregulation of COX-2-derived prostanoids. Pharmacol Res. 2018 Jul;133:236-249. doi: 10.1016/j.phrs.2018.01.001. Epub 2018 Jan 5. PMID: 29309904. 13: Leal MAS, Dias AT, Porto ML, Brun BF, Gava AL, Meyrelles SS, Gil-Longo J, Campos-Toimil M, Pereira TMC, Vasquez EC. Sildenafil (Viagra®) Prevents Cox-1/ TXA2 Pathway-Mediated Vascular Hypercontractility in ApoE-/- Mice. Cell Physiol Biochem. 2017;44(5):1796-1809. doi: 10.1159/000485817. Epub 2017 Dec 7. PMID: 29216624. 14: Sun P, Sun H, Zhang W, Du Z. Antagonist of thromboxane A2 receptor by SQ29548 lowers DOCA-induced hypertension in diabetic rats. Eur J Pharmacol. 2017 Nov 15;815:298-303. doi: 10.1016/j.ejphar.2017.09.028. Epub 2017 Sep 20. PMID: 28942103. 15: Chakraborti S, Sarkar J, Chowdhury A, Chakraborti T. Role of ADP ribosylation factor6- Cytohesin1-PhospholipaseD signaling axis in U46619 induced activation of NADPH oxidase in pulmonary artery smooth muscle cell membrane. Arch Biochem Biophys. 2017 Nov 1;633:1-14. doi: 10.1016/j.abb.2017.08.012. Epub 2017 Aug 16. PMID: 28822840. 16: Yan A, Zhang T, Yang X, Shao J, Fu N, Shen F, Fu Y, Xia W. Thromboxane A2 receptor antagonist SQ29548 reduces ischemic stroke-induced microglia/macrophages activation and enrichment, and ameliorates brain injury. Sci Rep. 2016 Oct 24;6:35885. doi: 10.1038/srep35885. PMID: 27775054; PMCID: PMC5075919. 17: Gonzalez-Paredes FJ, Hernández Mesa G, Morales Arraez D, Marcelino Reyes R, Abrante B, Diaz-Flores F, Salido E, Quintero E, Hernández-Guerra M. Contribution of Cyclooxygenase End Products and Oxidative Stress to Intrahepatic Endothelial Dysfunction in Early Non-Alcoholic Fatty Liver Disease. PLoS One. 2016 May 26;11(5):e0156650. doi: 10.1371/journal.pone.0156650. PMID: 27227672; PMCID: PMC4882009. 18: Huang SW, Kuo HL, Hsu MT, Tseng YJ, Lin SW, Kuo SC, Peng HC, Lien JC, Huang TF. A novel thromboxane receptor antagonist, nstpbp5185, inhibits platelet aggregation and thrombus formation in animal models. Thromb Haemost. 2016 Aug 1;116(2):285-99. doi: 10.1160/TH15-12-0993. Epub 2016 May 12. PMID: 27173725. 19: Kim HJ, Wie J, So I, Jung MH, Ha KT, Kim BJ. Menthol Modulates Pacemaker Potentials through TRPA1 Channels in Cultured Interstitial Cells of Cajal from Murine Small Intestine. Cell Physiol Biochem. 2016;38(5):1869-82. doi: 10.1159/000445549. Epub 2016 May 9. PMID: 27160463. 20: Liu Q, Tao B, Liu G, Chen G, Zhu Q, Yu Y, Yu Y, Xiong H. Thromboxane A2 Receptor Inhibition Suppresses Multiple Myeloma Cell Proliferation by Inducing p38/c-Jun N-terminal Kinase (JNK) Mitogen-activated Protein Kinase (MAPK)-mediated G2/M Progression Delay and Cell Apoptosis. J Biol Chem. 2016 Feb 26;291(9):4779-92. doi: 10.1074/jbc.M115.683052. Epub 2016 Jan 2. PMID: 26724804; PMCID: PMC4813499.