15-ketoLatanoprost is a potential metabolite of latanoprost when administered to animals. 15-ketoLatanoprost is also one of the common minor impurities found in commercial preparations of the bulk drug compound. Although much less potent that the parent compound latanoprost, 15-ketolatanoprost still retains 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-ketoLatanoprost is also a miotic in the normal cat eye, causing an 8 mm Hg reduction in pupillary diameter at 5 μg eye. Again, this is not as potent as many other F-type prostaglandins; for example, prostaglandin F2α will produce this degree of miosis at a dose of less than 1 μg eye.
Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (freeacid) by endogenous esterase enzymes. The freeacid form is 200 times more potent than latanoprost as a ligand for the human recombinant FP receptor. 5-trans Latanoprost (freeacid) is an isomer of latanoprost (freeacid) wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of latanoprost occurs as an impurity in commercial preparations of the bulk drug product. The present compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type prostaglandins, the biological activity of this isomer is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity, and on reducing intraocular pressure in particular, of 5-trans latanoprost.
Latanoprost 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 without isopropyl ester hydrolysis produces 15-ketolatanoprost. 15-ketoLatanoprost is a potential metabolite of latanoprost when administered to animals. 15-ketoLatanoprost is also one of the common minor impurities found in commercial preparations of the bulk drug compound. Although much less potent that the parent compound latanoprost, 15-ketolatanoprost still retains 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-ketoLatanoprost is also 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. Products of β-oxidation account for most of the metabolites of latanoprost recovered in plasma and urine. However, 15-ketolatanoprost is a minor metabolite, and one which could be enhanced in situations where β-oxidation is reduced.