prostaglandin f2α

A number of 17-phenyl trinor prostaglandin F2α (17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma. Of these, the unsubstituted or meta-substituted aromatic derivatives are the most potent FP receptor agonists. 17-trifluoromethylphenyl trinor PGF2α bears an aromatic ring which is reminiscent of the trifluoromethyl-phenoxy ring of travoprost ((+)-fluprostenol isopropyl ester). As an ocular hypotensive agent, it would be expected that 17-trifluoromethylphenyl trinor PGF2α would act very much like the free acid of travoprost. 17-phenyl trinor PGF2α is a potent luteolytic and abortifacient, with a potency equal to or greater than fluprostenol and cloprostenol.

Cloprostenol isopropyl ester is a PGF2α agonist and a similar synthetic prostaglandin F2α (PGF2α), which can induce luteal dissolution in mares during the luteal phase without causing clinical side effects or stress responses.

Bimatoprost is the Allergan trade name for 17-phenyl trinor prostaglandin F2α ethyl amide (17-phenyl trinor PGF2α ethyl amide), an F-series PG analog which has been approved for use as an ocular hypotensive drug. Oxidation of the C-15 hydroxyl group produces 15-keto-17-phenyl trinor PGF2α ethyl amide. 15-keto-17-phenyl trinor PGF2α ethyl amide is a potential metabolite of 17-phenyl trinor PGF2α ethyl amide when 17-phenyl trinor PGF2α ethyl amide is administered to intact animals. No pharmacological studies on 15-keto-17-phenyl trinor PGF2α ethyl amide have been reported.

17-phenyl trinor Prostaglandin F2α cyclopropyl amide (17-phenyl trinor PGF2α cyclopropyl amide) is a novel analog of 17-phenyl trinor PGF2α ethyl amide. There are no published reports on the biological activity of 17-phenyl trinor PGF2α cyclopropyl amide.

PGF2α isopropyl ester is an ester prodrug of PGF2α with enhanced lipid solubility. Due to better membrane penetration, PGF2α isopropyl ester is more suitable than PGF2α or PGF2α tromethamine salt for topical application in studies on intraocular pressure. The ester functionality is readily hydrolyzed in vivo to release the active compound PGF2α. When administered topically to the eyes of cynomolgus monkeys, a 5 μg dose reduces intraocular pressure by 68% after the fourth day of treatment.

17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor, binding with a relative potency of 756% compared to that of PGF2α. The ethyl amide of 17-phenyl trinor PGF2α bimatoprost has been approved for use as an ocular hypotensive drug. 17-phenyl trinor PGF2α methyl amide is an analog of bimatoprost. Its biological and toxicological properties have not been evaluated.

Prostaglandin F2α (PGF2α), acting through the FP receptor, causes smooth muscle contraction and exhibits potent luteolytic activity. 17-trifluoromethylphenyl trinor Prostaglandin F2α (17-trifluoromethylphenyl trinor PGF2α) is an analog of PGF2α that shares the meta-trifluoromethyl group of travoprost with the 17-phenyl trinor modification of latanoprost. It is anticipated to be a potent and selective agonist of the FP receptor, with potential applications in glaucoma and luteolysis. 17-trifluoromethylphenyl trinor PGF2α ethyl amide is a lipophilic analog of 17-trifluoromethylphenyl trinor PGF2α. Ethyl amides of PGs can serve as prodrugs, as they are hydrolyzed in certain tissues to generate the bioactive free acid.

Prostaglandin F2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Stable, lipophilic analogs of PGF2α are used to modulate luteolysis and treat glaucoma. 16-phenoxy tetranor Prostaglandin F2α (16-phenoxy tetranor PGF2α) is a metabolically stable form of PGF2α containing a 16-phenoxy group at the ω-terminus. It binds to the FP receptor on ovine luteal cells with much greater affinity (440%) than PGF2α. 16-phenoxy tetranor PGF2α methyl ester is a lipophilic analog of 16-phenoxy tetranor PGF2α. Methyl esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.

Bimatoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Oxidation of the C-15 hydroxyl group and amide hydrolysis of Bimatoprost produces 15-keto-17-phenyl trinor PGF2α. 15-keto-17-phenyl trinor PGF2α is a potential metabolite of bimatoprost when administered to animals. 15-keto PG analogs are potential minor impurities in commercial preparations of their corresponding bulk drug compounds. Although much less potent that the parent compound, 15-keto PGs still retain the ability to produce a small but measurable decrease (1 mm Hg) in the intraocular pressure of normal cynomolgus monkeys when administered at a dose of 1 μg/eye. 15-keto Latanoprost (15-keto-17-phenyl-13,14-dihydro trinor PGF2α isopropyl ester) is a miotic in the normal cat eye, causing an 8 mm reduction in pupillary diameter at 5 μg/eye. Again, this is not as potent as many other F-type PGs; for example, PGF2α will produce this degree of miosis at a dose of less than 1 μg/eye.

Prostaglandin F2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Stable, lipophilic analogs of PGF2α are used to modulate luteolysis and treat glaucoma. 16-phenoxy tetranor Prostaglandin F2α isopropyl ester (16-phenoxy tetranor PGF2α isopropyl ester) is a lipophilic analog of 16-phenoxy tetranor PGF2α. Isopropyl esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.

N-Desethyl Bimatoprost (17-phenyl trinor PGF2α amide) is an F-series PG analog in which the C-1 carboxyl group has been modified to an unsubstituted amide. PG esters have been shown to have ocular hypotensive activity. PG N-ethyl amides were recently introduced as alternative PG hypotensive prodrugs. Although it has been claimed that PG amides are not converted to the free acids in vivo, studies have shown that bovine and human corneal tissue converts the amides of various PGs to the free acids with a conversion efficiency of about 10-20% relative to the hydrolysis of isopropyl esters. 17-phenyl trinor PGF2α amide would be expected to show the typical intraocular effects of latanoprost, but with the much slower hydrolysis pharmacokinetics of the PG N-amides.

ent-Prostaglandin F2α is the enantiomer of PGF2α and is found in urine.

A number of 17-phenyl trinor prostaglandin F2α(17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma.1,2,3Of these, the ones wherein the 13,14-double bond has been hydrogenated retain relatively good potency, but show a significantly reduced incidence of local irritant side effects.417-trifluoromethylphenyl-13,14-dihydro trinor PGF2αbears an aromatic ring which is reminiscent of the trifluoromethyl-phenoxy ring of travoprost ((+)-fluprostenol isopropyl ester). As an ocular hypotensive agent, it would be expected that 17-trifluoromethylphenyl-13,14-dihydro trinor PGF2αwould act very much like the free acid of latanoprost.

Prostaglandin F2α (PGF2α), acting through the FP receptor, causes smooth muscle contraction and exhibits potent luteolytic activity. 17-trifluoromethylphenyl trinor PGF2α is an analog of PGF2α that shares the meta-trifluoromethyl group of travoprost with the 17-phenyl trinor modification of latanoprost. It is anticipated to be a potent and selective agonist of the FP receptor, with potential applications in glaucoma and luteolysis. 17-trifluoromethylphenyl trinor PGF2α methyl ester is a lipophilic analog of 17-trifluoromethylphenyl trinor PGF2α. Methyl esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.

Prostaglandin F2α (PGF2α), acting through the FP receptor, causes smooth muscle contraction and exhibits potent luteolytic activity. Both 17-phenyl trinor PGF2α and 16-phenoxy tetranor PGF2α are metabolically stable analogs of PGF2α and potent agonists for the FP receptor. 17-phenoxy trinor PGF2α ethyl amide is a lipophilic analog of 17-phenoxy trinor PGF2α . Ethyl amides of PGs serve as prodrugs, as they are hydrolyzed in certain tissues to generate the bioactive free acid.

8-Isoprostaglandin F2α is a natural product for research related to life sciences. The catalog number is T37164 and the CAS number is 27415-26-5.

20-hydroxy Prostaglandin F2α (20-hydroxy PGF2α) is the ω-oxidation product of PGF2α. Cultured type II alveolar cells from pregnant rabbits metabolize exogenous PGF2α via microsomal cytochrome P450 ω-oxidation, producing 20-hydroxy PGF2α and its 15-hydroxy PGDH metabolites. Cells from male rabbits exhibit only the 15-hydroxy PGDH pathway.

11β-Prostaglandin F2α is a bioactive metabolite catalyzed by AKR1C3 that stimulates prostaglandin F receptors and induces slug expression in breast cancer. 11β-Prostaglandin F2α is also an endogenous metabolite present in urine.

Prostaglandin F2α ethanolamide (PGF2α-EA) is produced by COX-2 metabolism of the endogenous cannabinoid, arachidonoyl ethanolamide (AEA), found in brain, liver, and other mammalian tissues. AEA can be metabolized directly by the sequential action of COX-2 and specific PG synthases to produce ethanolamide congeners of the classical PGs. PGF2α-EA has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of living mice. PGF2α-EA is a potent dilator (EC50 = 58 nM) of the cat iris sphincter, which is a model system for testing potential intraocular hypotensive agents.

17-phenyl trinor Prostaglandin F2αdimethyl amide is an isomer of 17-phenyl trinor prostaglandin F2αethyl amide . N/A

Prostaglandin F2α (PGF2α) activates the FP receptor, promoting smooth muscle contraction and luteolysis. 17-phenyl trinor PGF2α binds the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α. It is produced in vivo by the hydrolysis of 17-phenyl trinor PGF2α ethyl amide. 17-phenyl trinor PGF2α ethyl amide is used to reduce intraocular pressure related to glaucoma. 17-phenyl trinor PGF2α cyclopropyl methyl amide is a lipophilic analog of 17-phenyl trinor PGF2α. Amides of PGs may serve as prodrugs, as they are hydrolyzed in certain tissues to generate the bioactive free acid.

Prostaglandin F2α (PGF2α) drives luteolysis and smooth muscle contraction by activating the FP receptor. Bimatoprost methyl ester is a lipophilic analog of 17-phenyl trinor PGF2α, a potent agonist for the FP receptor. 17-phenyl trinor PGF2α binds the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α. Esters of PGs serve as prodrugs, as they are efficiently hydrolyzed in certain tissues to generate the bioactive free acid.

The actions of many clinical F-series prostaglandins (PGs), including those used for estrous synchronization and for reduction of intraocular pressure (IOP), are mediated through the PGF2α (FP) receptor. 16-phenoxy tetranor Prostaglandin F2α cyclopropyl methyl amide (16-phenoxy tetranor PGF2α cyclopropyl methyl amide) is an analog of PGF2α containing a 16-phenoxy group on the lower (ω) side chain and a cyclopropyl methyl amide at the C-1 position. There are no published reports on the biological activity of 16-phenoxy tetranor PGF2α cyclopropyl methyl amide.

16,16-dimethyl Prostaglandin F2α can be used in related research in the field of life sciences. Its product number is T37993 and CAS number is 39746-23-1.

Prostaglandin F2β (PGF2β) is the 9β-hydroxy stereoisomer of PGF2α. It is much less active than PGF2α in antifertility and bronchoconstrictor activities. PGF2β exhibits bronchodilating activity in guinea pigs and cats and antagonizes the bronchoconstrictor activity of PGF2α.

5’-O-DMT-N4-Bz-2’-F-dC is a nucleoside with protective and modification effects.

8-iso-15(R)-Prostaglandin F2α (8-iso-15(R) PGF2α) is a chemically distinct member within a broad group of prostaglandin-like eicosanoids, produced through the free radical peroxidation of arachidonic acid contained in membrane phospholipids. It represents the C-15 epimer of 8-isoPGF2α, distinguished as the sole isoprostane isomer extensively examined across numerous biological systems.

8-iso-13,14-dihydro-15-keto Prostaglandin F2α (8-iso-13,14-dihydro-15-keto PGF2α) is a metabolite of the isoprostane, 8-isoprostane (8-iso PGF2α), in rabbits, monkeys and humans. 8-iso PGF2α is a PG-like product of non-specific lipid peroxidation. In both humans and monkeys, exogenously infused 8-isoprostane is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation. A similar pattern is observed when tritiated 8-isoprostane is infused into rabbits. Early in the infusion (within 10 minutes) 8-iso-13,14-dihydro-15-keto PGF2α was a significant component of the metabolite profile, which was comprised mostly of dinor 8-isoprostane metabolites. 8-iso-13,14-dihydro-15-keto PGF2α weakly inhibits the U-46619 or collagen-induced aggregation of human platelets, although a number of the E-series isoprostanes are much more potent in this assay.

15-keto Prostaglandin F2α is a metabolite of Prostaglandin F2α that lowers intraocular pressure in rabbits.

17-Phenyl trinor Prostaglandin F2α isopropyl amide is a derivative of 17-phenyl trinor prostaglandin F2α ethyl amide.

5-trans-17-phenyl trinor Prostaglandin F2α (5-trans-17-phenyl trinor PGF2α) represents the 5-trans isomer and the free acid variant of 17-phenyl trinor PGF2α, distinct from its ethyl amide and dimethyl amide derivatives. This compound serves as a potential impurity in 17-phenyl trinor PGF2α formulations. It is utilized as an analytical standard for the detection and quantification of itself in 17-phenyl trinor PGF2α preparations.

Prostaglandin F2α Alcohol is a PGF2α (T15133) analogue. Prostaglandin F2α Alcohol is an orally active prostaglandin F receptor (FP receptor) agonist.

15(S)-15-methyl Prostaglandin F2α methyl ester can be used in related research in the field of life sciences. Its product number is T36156 and CAS number is 35700-21-1.

Bimatoprost grenod(15-(6-nitroxyhexanoyl)-17-phenyl trinor PGF2α) is a nitric oxide-donating derivative of 17-phenyl trinor PGF2α.1It increases cGMP levels in rabbit aqueous humor and iris ciliary body when topically administered at a concentration of 0.042%. Topical administration of 15-(6-nitroxylhexanoyl)-17-phenyl trinor PGF2α(0.14%) reduces intraocular hypertension (IOP) in a rabbit model of hypertonic saline-induced transient ocular pressure. It also reduces IOP in a cynomolgus monkey model of laser-induced ocular hypertension when administered topically at a concentration of 0.042%.

17-phenyl trinor Prostaglandin F2α N-ethyl amide (17-phenyl trinor PGF2α) is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name 17-phenyl trinor PGF2α ethyl amide. Investigations in our lab have shown that 17-phenyl trinor PGF2α ethyl amide is converted by an amidase enzymatic activity in the human cornea to yield the corresponding free acid, with a conversion rate of about 25 μg/cornea/24 hours. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. 15(R)-17-phenyl trinor PGF2α is the 15-epi, or unnatural isomer of this active free acid metabolite. It has much diminished FP receptor-mediated activity

Bimatoprost acid (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and has a potential antagonistic activity for the FP receptor. It has a relative potency of 756% compared to PGF2α for binding to the FP receptor on ovine luteal cells.

8,12-iso-iPF2α-VI, an isoprostane, arises from non-enzymatic, free radical-induced peroxidation of membrane lipids. It is the predominant isoprostane formed during lipid peroxidation and serves as a biomarker for oxidative stress. Detectable in hepatic tissue post CCl4-induced oxidative damage, 8,12-iso-iPF2α-VI levels are also elevated in the urine, blood, and cerebrospinal fluid of Alzheimer’s disease patients.

17-Phenyl trinor Prostaglandin F2αdiethyl amide (17-phenyl trinor PGF2αdiethyl amide) is a Prostaglandin F2α(PGF2α) analog characterized by the substitution of the C-1 carboxyl group with an N-diethyl amide. Prostaglandin (PG) esters and N-ethyl amides have demonstrated ocular hypotensive properties, with N-ethyl amides introduced as alternative options for PG hypotensive prodrugs. Studies indicate that both bovine and human corneal tissues can convert N-ethyl amides of various PGs into their free acid forms at a rate of approximately 2.5 µg/g corneal tissue/hr. However, dialkyl amides like 17-phenyl trinor PGF2αdiethyl amide resist conversion by corneal amidase, showing no detectable transformation into free acids. This characteristic suggests their potential as valuable investigative tools for assessing the intrinsic intraocular hypotensive activities of PG amides.

8-iso-15-keto Prostaglandin F2α (8-iso-15-keto PGF2α) is a metabolite of the isoprostane 8-iso PGF2α in rabbits, monkeys, and humans. 8-isoprostane (8-iso PGF2α) is a prostaglandin-like product of non-specific lipid peroxidation. In both humans and monkeys, exogenously infused 8-iso PGF2α is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation. A similar pattern is observed when tritiated 8-iso PGF2α is infused into rabbits. Early in the infusion (within 1-2 minutes) 8-iso -15-keto PGF2α was a major component of the metabolite profile, which was comprised mostly of unmetabolized 8-iso PGF2α. 8-iso -15-keto PGF2α is a vasoconstrictor when tested on the rat isolated thoracic aorta, acting via the TP (thromboxane) receptor.

Prostaglandin F2α 1,11-lactone (PGF2α 1,11-lactone) is a lipid-soluble prodrug of Prostaglandin F2α and can be used in studies about treating glaucoma. Prostaglandin F2α 1,11-lactone is active as an antifertility agent with greatly reduced vasoactivity.

15(S)-15-methyl Prostaglandin F2α (15(S)-15-methyl PGF2α) has been shown to have potent uterine stimulant and abortifacient properties when administered intramuscularly to induce labor. 15(S)-15-methyl PGF2α isopropyl ester is a lipophilic analog of 15(S)-15-methyl PGF2α methyl ester, which may be hydrolyzed in vivo to the fully active free acid.

17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost. The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost. This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost. At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.

Prostaglandin F2α (PGF2α) 1,9-lactone, a lipid-soluble internal ester of PGF2α, demonstrates resistance to hydrolysis by human plasma esterases, maintaining its structure even after 20 hours of incubation under physiological conditions. Unlike PGF2α, this compound exhibits minimal antifertility and vasoactivity.

Prostaglandin F2α-1-glyceryl ester undergoes oxidation via 15-hydroxyprostaglandin dehydrogenase (15-HPGDH) [1].

Carboprost (15(S)-15-Methyl Prostaglandin F2α) is a synthetic prostaglandin analogue of PGF2α which has the effect of oxytocic. Carboprost is commonly used to restore uterine tone.

13,14-dihydro Prostaglandin F2α (13,14-dihydro PGF2α) is the analog of PGF2α which has no unsaturation in the lower side chain. It causes luteolysis in hamsters with a potency five times higher than PGF2α. The ED50 value for 13,14-dihydro PGF2α as a luteolytic agent in hamsters is 1.5 µg/100 g.[1]

ent-8-iso Prostaglandin F2α is a potent vasoconstrictor of porcine retinal and cerebral microvessels with EC50 values of 30.6 and 53.5 nM, respectively.

Isoprostanes are produced by the non-enzymatic, free radical peroxidation of phospholipid-esterified arachidonic acid. They have been used as biomarkers of oxidative stress, but they also have been found to have potent biological activity. ent-8-iso-15(S)-Prostaglandin F2α (ent-8-iso-15(S)-PGF2α) is a potent vasoconstrictor of porcine retinal and brain microvessels with EC50 values of 15 and 24 nM, respectively. This isoprostane is about ten-fold more potent than 8-iso-PGF2α in a whole blood platelet aggregation inhibition assay.

Dinoprost tromethamine salt (PGF2α THAM) is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.

Prostaglandin F2α methyl ester is a highly lipid-soluble PGF2α analog used to maintain low intraocular pressure.

Dinoprost methoxyamine is a hormone.