Butaprost is a selective prostaglandin E receptor (EP2) agonist/activator with EC50 of 33 nM and a Ki of 2.4 μM for the murine EP2 receptor. Butaprost has low activity at murine EP1, EP3 and EP4 receptors. Butaprost attenuates fibrosis by blocking TGF-β/Smad2 signaling.

Physicochemical Properties

Molecular Formula	C24H40O5
Molecular Weight	408.57140827179
Exact Mass	408.287
Elemental Analysis	C, 70.55; H, 9.87; O, 19.58
CAS #	69685-22-9
PubChem CID	5311035
Appearance	Colorless to light yellow liquids at room temperature
Density	1.1±0.1 g/cm3
Boiling Point	525.1±50.0 °C at 760 mmHg
Flash Point	168.4±23.6 °C
Vapour Pressure	0.0±3.1 mmHg at 25°C
Index of Refraction	1.539
LogP	3.51
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	14
Heavy Atom Count	29
Complexity	552
Defined Atom Stereocenter Count	4
SMILES	CCCC1(CCC1)[C@H](C/C=C/[C@@H]2[C@@H](CCCCCCC(=O)OC)C(=O)C[C@H]2O)O
InChi Key	XRISENIKJUKIHD-UHFFFAOYSA-N
InChi Code	InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3
Chemical Name	methyl 7-[3-hydroxy-2-[4-hydroxy-4-(1-propylcyclobutyl)but-1-enyl]-5-oxocyclopentyl]heptanoate
Synonyms	BAY-q 4218;TR 4979; 69685-22-9; methyl 7-[3-hydroxy-2-[4-hydroxy-4-(1-propylcyclobutyl)but-1-enyl]-5-oxocyclopentyl]heptanoate; DTXSID20860901; Methyl 11,16-dihydroxy-9-oxo-17-propyl-17,20-cycloprost-13-en-1-oate;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	EP2 (prostaglandin E receptor)
ln Vitro	In hEP2-HEK293/EBNA cells, butaprost (1-100 nM; 0.5-24 hours) causes a dose- and time-dependent elevation of Nur77 mRNA expression of approximately five times. By activating the PKC pathway, butaprost increased the expression of the Nur77 gene[1]. In Madin-Darby Canine Kidney (MDCK) cells, butaprost (50 μM; 24 hours) decreases TGF-β-induced fibronectin (FN) production, Smad2 phosphorylation, and epithelial-mesenchymal transition[2].
ln Vivo	In mice undergoing surgery for unilateral ureteral obstruction, butaprost (1-4 mg/kg; intraperitoneal injection; twice daily; for 7 days) treatment reduces the development of fibrosis, as evidenced by a decrease in the expression of the α-smooth muscle actin, fibronectin, and collagen 1A1 genes and proteins[2].
Cell Assay	Western Blot Analysis[1] Cell Types: HEK 293/EBNA cells stably expressing the human EP2 receptor (hEP2-HEK 293/EBNA cells) Tested Concentrations: 1 nM, 10 nM, 100 nM Incubation Duration: 0.5 hrs (hours), 1 hour, 6 hrs (hours), 24 hrs (hours) Experimental Results: Induced about a five-fold upregulation of Nur77 mRNA expression in hEP2-HEK293/EBNA cells.
Animal Protocol	Animal/Disease Models: Male C57BL/6 mice (8 weeks of age; 21 g) bearing unilateral ureteral obstruction surgery[2] Doses: 1 mg/kg, 2 mg/kg, 4 mg/ kg Route of Administration: intraperitoneal (ip) injection; twice (two times) daily; for 7 days Experimental Results: Attenuated the development of fibrosis in mice that underwent unilateral ureteral obstruction surgery.
References	[1]. 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. 20. [2]. 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]. Design and synthesis of a highly selective EP2-receptor agonist. Bioorg Med Chem Lett. 2001 Aug 6;11(15):2025-8.
Additional Infomation	(R)-Butaprost is a prostanoid.

Solubility Data

Solubility (In Vitro)

Typically soluble in DMSO (e.g. >10 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4476 mL	12.2378 mL	24.4756 mL
	5 mM	0.4895 mL	2.4476 mL	4.8951 mL
	10 mM	0.2448 mL	1.2238 mL	2.4476 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.