5376. Latanoprost

Nomenclature

CAS number: 130209-82-4
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 1-methylethyl ester; isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate; 13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α-isopropyl ester; PhXA-41; Xalatan (Pharmacia & Upjohn).
C26H40O5; mol wt 432.59.
C 72.19%, H 9.32%, O 18.49%.

Description and references

Prostaglandin analog; prodrug of active acid metabolite. Prepd (not claimed): J. Ivanics et al., WO 9300329 (1993 to Kabi Pharmacia; Chinoin). Prepn: B. Resul et al., J. Med. Chem. 36, 243, 2242 (corr.) (1993). Clinical pharmacology: C. B. Toris et al., Ophthalmology 100, 1297 (1993). Clinical evaluation in glaucoma: P. Rácz et al., Arch. Ophthalmol. 111, 657 (1993); as single therapy and in combination with timolol, q.v.: A. H. Rulo et al., Br. J. Ophthalmol. 78, 899 (1994). Review of preclinical pharmacology: J. Stjernschantz et al., Adv. Prostaglandin Thromboxane Leukotriene Res. 23, 513-518 (1995).

Chemical structure

Properties

Colorless oil. [α]D20 +31.57° (c = 0.91 in acetonitrile). Very sol in acetonitrile; freely sol in acetone, ethanol, ethyl acetate, isopropanol, methanol, octanol. Practically insol in water.

Therapeutic Category

Antiglaucoma.

Keywords

Antiglaucoma; Prostaglandin/Prostaglandin Analog