8-iso PGF2β is an isomer of PGF2α with a non-enzymatic, non-cyclooxygenase origin. It is one of 64 possible isomers of PGF2α which can be produced by free radical peroxidation of arachidonic acid. 8-iso PGF2β exhibits very weak contraction of human umbilical vein artery and…

A potent and selective competitive antagonist of the EP1 receptor (Ki = 0.6 and 1.7 nM for human and mouse EP1, respectively); effectively reduces tumor incidence and multiplicity in mouse models of colon, breast, and oral cancer; suppresses pain and acid-induced HCO₃- secretion in the stomach.

PGF2α-NEt is an analog of PGF2α in which the C-1 carboxyl group has been modified to an N-ethyl amide. PG esters have been shown to have ocular hypotensive activity. PG N-ethyl amides were recently introduced as alternative prostaglandin ocular hypotensive prodrugs. Although it has been…

TXA2 receptor agonist; causes platelet shape change (EC₅₀ ~6 nM) and aggregation (EC₅₀ ~97 nM).

11β-PGE2 is the C-11 epimer of PGE2. It is a moderate inhibitor of PGE2 binding to rat hypothalamic membranes with a Ki value of 53 nM. 11β-PGE2 also stimulates bone resorption in rats at concentrations of 10-8 to 10-6 M which is similar to PGE2. 11β-PGE2 inhibits PGE2 binding to the…

A potential metabolite of bimatoprost when administered to animals; potential minor impurity in commercial preparations of bimatoprost.

A stable, cell-permeable form of α-ketoglutarate which accumulates rapidly and preferentially in cells with a dysfunctional TCA cycle; stimulates PHD activity and increases HIF-1α turnover when used at 1 mM; competitively blocks succinate- or fumarate-mediated inhibition of PHD.

A potent and selective G9a HMTase inhibitor (IC50 = 6 nM; Ki = 63 pM); more than 40,000-fold selective for G9a over SET7/9, SET8, PRMT3, and JMJD2E.

A competitive inhibitor of 15-hydroxy PGDH; acts as an agonist on most EP receptor subtypes (Kd d~ 1 nM for isolated EP2 receptors); preserves the self-renewal properties while preventing the differentiation of hematopoietic stem cells during expansion in culture.

PGB2 is a non-enzymatic dehydration product resulting from the treatment of PGE2 or PGA2 with strong base. It has weak agonist activity on TP receptors and can increase pulmonary blood pressure in the rabbit at relatively high doses (5 µg/kg).

AFC is a synthetic substrate for the isoprenylated protein methyltransferase (also known as S-adenosylmethionine-dependent methyltransferase). Because it is able to serve as a substrate for the methyltransferase, it effectively functions as an inhibitor of methylation of endogenous isoprenylated proteins.

A FAHFA consisting of palmitoleic acid esterified at the 9-position of hydroxy stearic acid; significantly elevated in serum of glucose tolerant AG4OX mice; may be a bioactive lipid with roles in metabolic syndrome and inflammation.

Iloprost is a second generation structural analog of prostacyclin (PGI) with about ten-fold greater potency than the first generation stable analogs, typified by carbaprostacyclin. Iloprost binds with equal affinity to the human recombinant IP and EP1 receptors with a Ki of 11 nM. Iloprost…

A number of 17-phenyl trinor PGF2α derivatives have been approved for the treatment of glaucoma. Of 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.…

16,16-dimethyl PGF2β is a metabolically stable analog of PGF2β. It prevents bronchospasm in asthmatics but is less potent than PGE2.

A plant growth regulator that activates various signal transduction pathways with both growth promoting and inhibitory functions, perhaps in response to stress; initially synthesized as (+)7-epi jasmonic acid, a more active and biologically relevant form of the hormone, but quickly epimerizes to…

An isomer of 17-phenyl trinor PGF2α, characterized by an inverted (β) hydroxyl group at C-15.

A form of FAHFA in which oleic acid is esterified to 13-hydroxy stearic acid.

13,14-dihydro-15-keto PGF1α is a metabolite of PGF1α that has been reported in the rat stomach. The measurement of 13,14-dihydro-15-keto PGF1α can be used as a marker of the in vivo production of PGF1α.

15(R)-PGF2α is the C-15 epimer of the naturally occurring mammalian autacoid PGF2α. It has only 25% of the potency of PGF2α in hamster antifertility studies, which may be due to reduced affinity for FP receptors. Compared to PGF2α, 15(R)-PGF2α has a binding affinity of…

A lipid peroxidation product; actively modifies histidine and lysine residues on proteins and causes protein cross-linking.

A FAHFA in which palmitic acid is esterified to 9-hydroxy palmitic acid.

Butaprost is a structural analog of PGE2 with good selectivity for the EP2 receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells. Serious confusion as to the structure of Butaprost was…

17-phenyl trinor PGA2 is a synthetic prostaglandin analog designed for increased half-life and greater potency. There are no published reports of the biological activity of 17-phenyl trinor PGA2 in the literature at this time.

An analog of latanoprost in which the hydroxyl at C-15 is inverted relative to latanoprost; binds to the FP receptor in the cat iris sphincter muscle with an IC₅₀ value of 24 µM (tested as the free acid); potential impurity in latanoprost bulk drug preparations.

An internal standard for the quantification of linoleic acid by GC- or LC-MS.

A more lipid soluble derivative of Tafluprost, a very potent FP receptor agonist (Ki = 0.4 nM).

Unoprostone isopropyl ester (Rescula) is the clinically approved, prodrug form of unoprostone, which is a free acid analog of PGF2α. Both latanoprost and Rescula have been approved for the treatment of ocular hypertension. Both analogs of PGF2α are believed to act by increasing the rate…

A potent and selective EP1 receptor antagonist (IC₅₀ = 2.5 nM), with >400-fold selectivity relative to EP2, EP3, EP4, DP1, and IP; has 30-fold selectivity over TP; shows complete anti-hyperalgesic activity in a rat model of chronic inflammatory joint pain.

A dehydration product of PGD2 formed by the elimination of the C-9 hydroxyl group; inhibits platelet aggregation (IC₅₀ ~ 5-10 nM); has antimitotic and antiproliferative effects on a variety of cultured normal cells and tumor cell lines.

An analog of MAFP, which has been widely studied as an inhibitor of phospholipases, FAAH, and as a CB receptor ligand; pharmacology of the α-linolenyl analog of MAFP has not been completely investigated.

20-ethyl PGE2 is an analog of PGE2 in which the ω-chain has been extended by the addition of two methylene carbon atoms. The only well studied prostaglandin analog with this structural feature is unoprostone, an F-series prostaglandin that is clinically approved as a glaucoma medication.…