There are currently four prostaglandin (PG) derivatives which have been approved for human clinical use for the treatment of glaucoma. The names of the PGs and the concentrations of the approved doses are: travoprost (40 μg/ml), latanoprost (50 μg/ml), bimatoprost (300 μg/ml), and unoprostone (1,500 μg/ml). All of these compounds are modified at C-1 in order to act as lipophilic prodrugs in the eye. All have also been postulated to function via activation of the prostanoid FP receptor. Unoprostone and bimatoprost stand out in this class due to their lack of potency. Both are also claimed to have alternate mechanisms of actions: as a docosanoid in the case of unoprostone and as a prostamide in the case of bimatoprost. Lumula is a hybrid eicosanoid analog which incorporates the docosanoid features of unoprostone as well as the prostamide features of bimatoprost. Based on classical structure-activity relationships which have been established for prostanoid receptors
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.