-Fluprostenol Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C23H29F3O6 |
| Molecular Weight | 458.47 |
| Exact Mass | 458.191 |
| Elemental Analysis | C, 60.25; H, 6.38; F, 12.43; O, 20.94 |
| CAS # | 54276-17-4 |
| Related CAS # | 55028-71-2 (sodium); 40666-16-8 (free acid); 54276-17-4 (rotation positive) |
| PubChem CID | 5311100 |
| Appearance | Colorless to light yellow ointment at room temperature |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 608.0±55.0 °C at 760 mmHg |
| Flash Point | 321.5±31.5 °C |
| Vapour Pressure | 0.0±1.8 mmHg at 25°C |
| Index of Refraction | 1.575 |
| LogP | 2.55 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 32 |
| Complexity | 636 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | FC(C1C=CC=C(C=1)OC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O)(F)F |
| InChi Key | WWSWYXNVCBLWNZ-QIZQQNKQSA-N |
| InChi Code | InChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1 |
| Chemical Name | (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoic acid |
| Synonyms | Travoprost acid; (+)-fluprostenol; 54276-17-4; 40666-16-8; Fluprostenol, (+)-; travoprost free acid; Fluprostenolum; AL-5848; AL5848 |
| 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 | PTGER2[1] |
| ln Vitro | In the present study, we evaluated the effects of the PTGER2 agonist butaprost and the PTGFR agonist fluprostenol on OVGP1 mRNA and protein levels in BOECs using RT-qPCR and western blotting, respectively. Our results showed that butaprost and fluprostenol significantly promoted and suppressed OVGP1 expression in BOECs, respectively. Moreover, PGE2 was shown to promote expression of OVGP1 through its receptor PTGER2, and PGF2α to exert a down regulatory effect on OVGP1 via activation of its receptor PTGFR. Furthermore, the possibility that PGE2 and PGF2α affect OVGP1 through the PTGER2-cAMP-PKA and PTGFR-Ca2+-PKC signaling pathways, respectively, has been strengthened by our data[1]. |
| Cell Assay | Butaprost (a PTGER2 agonist, 10–6 M) and fluprostenol (a PTGFR agonist, 10–6 M) were added to the experimental BOECs cultures, and the experimental and control BOECs were cultured in separate dishes in parallel. Expression of OVGP1 was subsequently measured after 2, 4, 8, 16, 24, and 48 h and compared to that of the cells cultured in the absence of receptor agonists. H-89 (a PKA inhibitor, 3 μM), chelerythrine chloride (a PKC inhibitor, 5 μM), and U0126 (an ERK inhibitor, 3 μM) were added to the experimental BOECs cultures, and the experimental and control BOECs were then cultured in separate dishes in parallel. OVGP1 expression was determined after 4 h and compared with that of cells cultured in the absence of inhibitors. |
| References |
[1]. The prostaglandin E2 receptor PTGER2 and prostaglandin F2α receptor PTGFR mediate oviductal glycoprotein 1 expression in bovine oviductal epithelial cells. J Reprod Dev. 2018;64(2):101-108. |
| Additional Infomation | Fluprostenol is an organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea. It has a role as an antiglaucoma drug, an antihypertensive agent, a prostaglandin receptor agonist, a female contraceptive drug and an abortifacient. It is a prostaglandins Falpha, a hydroxy monocarboxylic acid and a member of (trifluoromethyl)benzenes. |
Solubility Data
| Solubility (In Vitro) | DMSO: 330 mg/mL (719.79 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 8.25 mg/mL (17.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 82.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 8.25 mg/mL (17.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 82.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 8.25 mg/mL (17.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 82.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1812 mL | 10.9058 mL | 21.8117 mL | |
| 5 mM | 0.4362 mL | 2.1812 mL | 4.3623 mL | |
| 10 mM | 0.2181 mL | 1.0906 mL | 2.1812 mL |