Latanoprost

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Latanoprost
Latanoprost.svg
Latanoprost-3D-balls.png
Systematic (IUPAC) name
isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2- [(3R)3-hydroxy-5-phenylpentyl]-cyclopentyl] hept-5-enoate
Clinical data
Trade names Xalatan
AHFS/Drugs.com monograph
MedlinePlus a697003
Pregnancy cat. C (US)
Legal status -only (US)
Routes Topical (eye drops)
Pharmacokinetic data
Half-life 17 minutes
Identifiers
CAS number 130209-82-4 YesY
ATC code S01EE01
PubChem CID 5311221
IUPHAR ligand 1961
DrugBank DB00654
ChemSpider 4470740 YesY
UNII 6Z5B6HVF6O YesY
KEGG D00356 YesY
ChEBI CHEBI:6384 YesY
ChEMBL CHEMBL1051 YesY
Chemical data
Formula C26H40O5 
Mol. mass 432.593 g/mol
 YesY (what is this?)  (verify)

Latanoprost (pronounced la-TA-noe-prost) ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension by reducing intraocular pressure. It is a prostaglandin analogue (more specifically an analogue of prostaglandin F[1]) that works by increasing the outflow of aqueous fluid from the eyes (through the uvealsclearal tract).[2] Latanoprost is an isopropyl ester prodrug, that is hydrolyzed by esterases in the cornea to the biologically active acid.[3]


It is also known by the brand name of Xalatan manufactured by Pfizer. Annual sales are approximately $1.6 billion. The patent for latanoprost expired in March 2011, and at least one generic version (manufactured by Mylan Inc.) is now widely available in the U.S. The Veterans Health Administration, part of the U.S. Department of Veterans Affairs, uses generic Latanoprost manufactured by Alcon Laboratories of Fort Worth, Texas distributed by Novartis generic brand Sandoz Pharmaceuticals.

Latanoprost was invented by Johan W. Stjernschantz and Bahram Resul, employees of the Pharmacia Corporation of Upsalla, Sweden. [4]

Adverse reactions[edit]

Possible side effects:

  • May eventually cause permanent darkening of the iris to brown (heterochromia);
  • May cause reddening of the eyes (hyperemia)
  • May cause blurred vision;
  • May cause eyelid redness;
  • May permanently darken eyelashes;
  • May cause eye discomfort;
  • May cause a temporary burning sensation during use.
  • May cause thickening of the eyelashes.(used,also bimatoprost,in cosmetic industry as eyelash growth enhancers)
  • Rarely, herpes simplex keratitis.
  • A single case report links latanoprost use to the progression of keratoconus.[5]

See also[edit]

References[edit]

  1. ^ Ishikawa H, Yoshitomi T, Mashimo K, Nakanishi M, Shimizu K (February 2002). "Pharmacological effects of latanoprost, prostaglandin E2, and F2alpha on isolated rabbit ciliary artery". Graefes Arch. Clin. Exp. Ophthalmol. 240 (2): 120–5. doi:10.1007/s00417-001-0412-4. PMID 11931077. 
  2. ^ Patel SS, Spencer CM (1996). "Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension". Drugs Aging 9 (5): 363–378. PMID 8922563. 
  3. ^ Huttunen et al. (2011) Prodrugs—from Serendipity to Rational Design. Pharmacol Rev 63:750–771
  4. ^ "Patent US5296504 - Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension - Google Patents". 
  5. ^ Amano S, Nakai Y, Ko A, Inoue K, Wakakura M (2008). "A case of keratoconus progression associated with the use of topical latanoprost". Jpn. J. Ophthalmol. 52 (4): 334–6. doi:10.1007/s10384-008-0554-6. ISBN 38400805546 Check |isbn= value (help). PMID 18773275. 

External links[edit]