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69685-22-9

69685-22-9 structure
69685-22-9 structure
  • Name: Butaprost
  • Chemical Name: Butaprost
  • CAS Number: 69685-22-9
  • Molecular Formula: C24H40O5
  • Molecular Weight: 408.571
  • Catalog: Signaling Pathways GPCR/G Protein Prostaglandin Receptor
  • Create Date: 2017-04-15 10:26:07
  • Modify Date: 2024-01-02 10:43:45
  • Butaprost is a selective prostaglandin E receptor (EP2) agonist with a Ki of 2.4 μM for murine EP2 receptor. Butaprost is less activity against murine EP1, EP3 and EP4 receptors. Butaprost effectively mitigates renal fibrogenesis[1][2][3].

Name Butaprost
Synonyms 17,20-Cycloprost-13-en-1-oic acid, 11,16-dihydroxy-9-oxo-17-propyl-, methyl ester, (11α,13E,16S)-
Methyl (11α,13E,16S)-11,16-dihydroxy-9-oxo-17-propyl-17,20-cycloprost-13-en-1-oate
Description Butaprost is a selective prostaglandin E receptor (EP2) agonist with a Ki of 2.4 μM for murine EP2 receptor. Butaprost is less activity against murine EP1, EP3 and EP4 receptors. Butaprost effectively mitigates renal fibrogenesis[1][2][3].
Related Catalog
Target

m-EP2 receptor:2400 nM (Ki)

m-EP2 receptor:33 nM (EC50)

In Vitro Butaprost (1-100 nM; 0.5-24 hours) induces about a five-fold upregulation of Nur77 mRNA expression in hEP2-HEK293/EBNA cells in a dose- and time-dependent. Butaprost upregulated Nur77 gene expression through the PKC pathway[1]. Butaprost (50 μM; 24 hours) reduces TGF-β-induced fibronectin (FN) expression, Smad2 phosphorylation and epithelial-mesenchymal transition in Madin-Darby Canine Kidney (MDCK) cells[2]. Western Blot Analysis[1] Cell Line: HEK 293/EBNA cells stably expressing the human EP2 receptor (hEP2-HEK 293/EBNA cells) Concentration: 1 nM, 10 nM, 100 nM Incubation Time: 0.5 hours, 1 hours, 6 hours, 24 hours Result: Induced about a five-fold upregulation of Nur77 mRNA expression in hEP2-HEK293/EBNA cells.
In Vivo Butaprost (1-4 mg/kg; intraperitoneal injection; twice daily; for 7 days) treatment attenuates the development of fibrosis in mice that underwent unilateral ureteral obstruction surgery, as illustrated by a reduction in the gene and protein expression of α-smooth muscle actin, fibronectin and collagen 1A1[2]. Animal Model: Male C57BL/6 mice (8 weeks of age; 21 g) bearing unilateral ureteral obstruction surgery[2] Dosage: 1 mg/kg, 2 mg/kg, 4 mg/kg Administration: Intraperitoneal injection; twice daily; for 7 days Result: Attenuated the development of fibrosis in mice that underwent unilateral ureteral obstruction surgery.
References

[1]. Yanbin Liang, et al. Upregulation of orphan nuclear receptor Nur77 following PGF(2alpha), Bimatoprost, and Butaprost treatments. Essential role of a protein kinase C pathway involved in EP(2) receptor activated Nur77 gene transcription. Br J Pharmacol. 2004 Jun;142(4):737-48.

[2]. Michael Schou Jensen, et al. Activation of the prostaglandin E 2 EP 2 receptor attenuates renal fibrosis in unilateral ureteral obstructed mice and human kidney slices. Acta Physiol (Oxf). 2019 Sep;227(1):e13291.

[3]. K Tani, et al. Design and synthesis of a highly selective EP2-receptor agonist. Bioorg Med Chem Lett. 2001 Aug 6;11(15):2025-8.

Density 1.1±0.1 g/cm3
Boiling Point 525.1±50.0 °C at 760 mmHg
Molecular Formula C24H40O5
Molecular Weight 408.571
Flash Point 168.4±23.6 °C
Exact Mass 408.287567
PSA 83.83000
LogP 3.51
Vapour Pressure 0.0±3.1 mmHg at 25°C
Index of Refraction 1.539
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