Polar C-1 esters of prostaglandins

An ophthalmic solution comprising a therapeutically effective amount of a compound of formula (I) ##STR10## wherein the wavy line attachments indicate either alpha (.alpha.) or beta (.beta.) configuration;

• hatched lines indicate .alpha. configuration, solid triangles are used to indicate .beta. configuration;
• the dashed bonds represent a single bond or a double bond which can be in the cis or trans configuration;
• X is selected from the group consisting of O, NH, S, and NR, where R is an aliphatic hydrocarbon group of 1 to about 6 carbon atoms;
• Y is a polar functional group selected from the group consisting of 1 to about 6 carbon hydroxy- or amino-substituted alkyl, a carboxyl moiety, an aminocarbonyl moiety, a sulfonic acid and a phosphonic acid, the alkyl groups of said Y groups may optionally be substituted with hydroxyl, nitro, chlorine or fluorine;
• one of R.sub.1 and R.sub.2 is .dbd.O, --OH or a --O(CO)R.sub.4 group, the other one is --OH or a --O(CO)R.sub.4 group or R.sub.1 is .dbd.O and R.sub.2 is H;
• R.sub.3 is --OH or --O(CO)R.sub.4 wherein R.sub.4 is a saturated or unsaturated, branched or straight-chained acyclic hydrocarbon group having from 1 to about 20 carbon atoms, or --(CH.sub.2).sub.n R.sub.5 wherein n is 0-10, and R.sub.5 is a saturated or unsaturated aliphatic ring from 3 to about 7 carbon atoms, or a phenyl or monoheteroaromatic ring consisting of 5 or 6 atoms one of which is O, N, or S;
• or a pharmaceutically acceptable salt thereof, or an ophthalmically acceptable salt thereof, in admixture with a non-toxic, opthalmically acceptable liquid vehicle, packaged in a container suitable for metered application.