| Size | Price | Stock | Qty |
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| Targets |
PTGER2[1]
(+)-Fluprostenol targets the Prostaglandin F2alpha receptor (FP receptor), a member of the G-protein coupled receptor (GPCR) family. It also exhibits potent agonistic activity towards PTGER2. The binding to the FP receptor influences various downstream signaling pathways critical for muscle contraction and cell survival. |
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| 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].
(+)-Fluprostenol effectively inhibits PGF2alpha binding to human and rat FP receptors with respective IC50 values of 3.5 nM and 7.5 nM, demonstrating high affinity. It is reported to reduce the expression of oviduct glycoprotein 1 (OVGP1) in in vitro cellular models, directly impacting reproductive cell function. |
| ln Vivo |
Specific in vivo activity data for (+)-Fluprostenol is limited; however, its non-chiral parent compound Fluprostenol is a synthetic PGF2alpha analog known to function as a luteolytic agent, inducing regression of the corpus luteum in animal models. It is also employed in ophthalmic research to modulate intraocular pressure.
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| Enzyme Assay |
The specific protocol for (+)-Fluprostenol may involve competitive radioligand binding assays using cell membrane homogenates expressing recombinant human or rat FP receptors. Membranes are incubated with varying concentrations of the compound and a fixed concentration of radiolabeled PGF2alpha. Non-specific binding is determined in the presence of excess non-labeled PGF2alpha. After incubation at room temperature, bound and free radioligands are separated via filtration through glass fiber filters, and the radioactivity retained on filters is measured using a scintillation counter to calculate IC50 values.
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| 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.
In a typical in vitro cellular assay, cultured cells (e.g., Human Trabecular Meshwork cells) are serum-starved overnight and then treated with varying concentrations of (+)-Fluprostenol (0.1 nM to 10 uM) for specific durations (2-48 hours). The treated cells are lysed for Western blotting to detect phosphorylation of intracellular signaling proteins (e.g., ERK, Akt) or to measure changes in gene expression (e.g., OVGP1, cyclooxygenase-2) via quantitative real-time PCR. Alternatively, FP receptor functional activity can be assessed in cells stably expressing the FP receptor by measuring the accumulation of intracellular inositol phosphates. |
| Animal Protocol |
Typical in vivo experiments involve administering (+)-Fluprostenol to female rodents to evaluate luteolysis. Doses may be administered subcutaneously (e.g., 1-10 mg/kg) or intramuscularly. Endpoints include measurement of serum progesterone levels, microscopic examination of ovarian tissue for corpus luteum regression, and monitoring of estrous cycle changes. In ophthalmic models, the compound is administered topically as an eye drop to normotensive or ocular hypertensive animal models (rabbits or non-human primates), followed by intraocular pressure measurements using a tonometer at multiple time points post-instillation over a 24-48 hour period.
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| ADME/Pharmacokinetics |
As a synthetic PGF2alpha analog, (+)-Fluprostenol is primarily used for topical ophthalmic administration, and systemic pharmacokinetic studies are limited. When administered via injection, it is expected to have a short plasma half-life due to rapid metabolic deactivation, primarily via beta-oxidation of the side chain. Its primary clearance mechanism is likely hepatic metabolism followed by renal excretion of inactive metabolites.
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| Toxicity/Toxicokinetics |
Detailed toxicological profiles for (+)-Fluprostenol are primarily derived from studies on related prostaglandin analogs. Expected side effects are local in nature following topical administration, such as mild conjunctival hyperemia, ocular irritation, and potential darkening of periorbital skin. With systemic administration, classic prostaglandin-related toxicities including gastrointestinal disturbances and smooth muscle contraction effects may occur. No specific long-term carcinogenicity studies are identified.
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| References | |
| Additional Infomation |
Fluoroprostol is an organofluorine compound, a racemic prostaglandin F2α, in which the pentyl group is replaced by 3-(trifluoromethyl)phenoxymethyl. Its isopropyl ester prodrug, travoprost, is an ophthalmic solution of prostaglandin F2α and can be used topically to control the progression of open-angle glaucoma and intraocular pressure by lowering intraocular pressure. The isopropyl ester group of travoprost is hydrolyzed in the cornea by esterases to a biologically active free acid. It has multiple uses, including anti-glaucoma, antihypertensive, prostaglandin receptor agonist, female contraceptive, and abortifacient. It is a prostaglandin Fα, a hydroxymonocarboxylic acid, belonging to the (trifluoromethyl)benzene class of compounds.
(+)-Fluprostenol is a key research tool in prostaglandin biology, specifically for studying FP receptor pharmacology. Its primary mechanism involves the activation of Gq-coupled FP receptors leading to increased intracellular calcium and activation of protein kinase C. It is not approved for therapeutic use in humans, unlike some of its derivatives. The (+) enantiomer is preferred in research due to its enhanced potency. |
| Molecular Formula |
C23H29F3O6
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|---|---|
| Molecular Weight |
458.47
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| Exact Mass |
458.191
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| Elemental Analysis |
C, 60.25; H, 6.38; F, 12.43; O, 20.94
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| CAS # |
54276-17-4
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| Related CAS # |
55028-71-2 (sodium); 40666-16-8 (free acid); 54276-17-4 (rotation positive)
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| PubChem CID |
5311100
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| Appearance |
Colorless to light yellow ointment at room temperature
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
608.0±55.0 °C at 760 mmHg
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| Flash Point |
321.5±31.5 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.575
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| LogP |
2.55
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
32
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| Complexity |
636
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| Defined Atom Stereocenter Count |
5
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| 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
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| InChi Key |
WWSWYXNVCBLWNZ-QIZQQNKQSA-N
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| 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
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| 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
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| Synonyms |
Travoprost acid; (+)-fluprostenol; 54276-17-4; 40666-16-8; Fluprostenol, (+)-; travoprost free acid; Fluprostenolum; AL-5848; AL5848
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: 330 mg/mL (719.79 mM)
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|---|---|
| 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. View More
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. |
| 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 |
*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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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