98672-91-4

Usage

Uses

Used in Pharmaceutical Industry:
SQ 29,548 is used as a pharmaceutical agent for the treatment of various cardiovascular and respiratory disorders. Its ability to inhibit platelet aggregation and antagonize smooth muscle contractions makes it a promising candidate for the management of conditions such as thrombosis, atherosclerosis, and asthma.
Used in Research Applications:
SQ 29,548 is employed as a research tool for studying the role of thromboxane A2 receptors in various physiological and pathological processes. Its high selectivity and potency allow researchers to investigate the specific mechanisms and pathways associated with these receptors, leading to a better understanding of their function and potential therapeutic targets.
Used in Drug Development:
SQ 29,548 serves as a lead compound in the development of new drugs targeting thromboxane A2 receptors. Its unique properties and effectiveness in inhibiting platelet aggregation and smooth muscle contractions can be leveraged to design and synthesize novel compounds with improved pharmacological profiles and therapeutic potential.

in vitro

in guinea-pig trachea and rat aorta, sq 29,548 competitively antagonized the activity of 9,11-azo pgh2 with pa2 values of 7.8 and 8.4, respectively. sq 29,548 competitively antagonized contractions of guinea-pig tracheal spirals induced by 11,9-epoxymethano pgh2 with the pa2 value of 9.1. the sq 29,548 competitively antagonized tracheal induced by 11,9-epoxymethano pgh2 and pgd2 with the pa2 values of 8.2 and 8.3, respectively. sq 29,548 partially antagonized the contractions of guinea-pig tracheal spirals caused by pge2. sq 29,548 significantly inhibited the aorta contracting activity of 11,9-epoxymethano pgh2 (pa2 = 9.1) and thromboxane a2 released from perfused guinea-pig lungs upon arachidonic acid challenge [1].

in vivo

in anesthetized dogs, sq 29,548 (0.2 mg/kg/h) completely inhibited the vasoconstrictor response of the left circumflex coronary artery (lcx) caused by u-46619. sq 28,585 showed no effects on infarct size as compared with vehicle controls [3]. in sham mi rats, treatment with sq-29,548 significantly blunted this loss of ck activity and amino-nitrogen concentration from the ischemic myocardium. sq-29,548 significantly prevented the extension of ischemic damage in the myocardium and improved survival following acute coronary artery ligation [4].

references

[1] ogletree m l, harris d n, greenberg r, et al. pharmacological actions of sq 29,548, a novel selective thromboxane antagonist[j]. journal of pharmacology and experimental therapeutics, 1985, 234(2): 435-441.[2] abe t, takeuchi k, takahashi n, et al. rat kidney thromboxane receptor: molecular cloning, signal transduction, and intrarenal expression localization[j]. journal of clinical investigation, 1995, 96(2): 657.[3] grover g j, schumacher w a. effect of the thromboxane receptor antagonist sq 29,548 on myocardial infarct size in dogs[j]. journal of cardiovascular pharmacology, 1988, 11(1): 29-35.[4] hock c e, brezinski m e, lefer a m. anti-ischemic actions of a new thromboxane receptor antagonist, sq-29,548, in acute myocardial ischemia[j]. european journal of pharmacology, 1986, 122(2): 213-219.

InChI:InChI=1/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

Upstream product

• 128781-29-3 methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<<2-<(phenylamino)carbonyl>hydrazino>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 
• 94903-80-7 [1S-[1α,2α(5Z)3α,4α]]-7-[3-Formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester 
• 128781-28-2 methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<<2-<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 
• 537-47-3 4-phenyl-semicarbazide 
• 128781-29-3 C₂₂H₃₁N₃O₄ 
• 104596-33-0 methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 
• 128781-28-2 C₂₂H₂₉N₃O₄ 

Relevant academic research and scientific papers

7-Oxabicycloheptyl Carboxylic Acids as Thromboxane A2 Antagonists: Aza ω-Chain Analogues

A novel bicyclic prostaglandin analogue, >-7-acetyl>amino>methyl>-7-oxabicyclohept-2-yl>-5-heptenoic acid ((-)-7) was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist.Unlike the related series of ω-chain allylic alcohols, amide 7 and its congeners were uniformly free of direct contractile activity in vitro (bovine coronary) and in vivo (anesthetized guinea pig).Amide 7 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-richplasma (I50 = 0.18 +/- 0.006 μM), (b) 11,9-epoxymethano-PGH2 induced platelet aggregation of human platelet-rich plasma (I50 = 0.24 μM), (c) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (Kb = 3.0 +/- 0.3 nM) or rat aorta (Kb = 8.8 +/- 1.1 nM), and (d) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (0.1-1.0 mg/kg iv).Amide 7 inhibited the binding of ->-7-hydrazino>methyl>-7-oxabicyclohept-2-yl>-5-heptenoic acid to human platelet membranes in a specific and saturable manner with a Kd = 49.6 +/- 1.4 nM.