Latanoprost

Latanoprost
Clinical data


Pronunciation	la-TAN-oh-prost
Trade names	Xalatan, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697003
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (eye drops)
ATC code	S01EE01 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Activation by ester hydrolysis, deactivation by beta oxidation
Onset of action	3–4 hours
Biological half-life	17 minutes (plasma)
Duration of action	≥ 24 hours
Excretion	Mainly via kidney
Identifiers
IUPAC name Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2- [(3R)3-hydroxy-5-phenylpentyl]-cyclopentyl] hept-5-enoate
CAS Number	130209-82-4^Y
PubChem CID	5311221
IUPHAR/BPS	1961
DrugBank	DB00654^Y
ChemSpider	4470740^Y
UNII	6Z5B6HVF6O
KEGG	D00356^Y
ChEBI	CHEBI:6384^Y
ChEMBL	CHEMBL1051^Y
ECHA InfoCard	100.162.178
Chemical and physical data
Formula	C₂₆H₄₀O₅
Molar mass	432.593 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OC(C)C)CCC/C=C\C[C@H]2[C@@H](O)C[C@@H](O)[C@@H]2CC[C@@H](O)CCc1ccccc1
InChI InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1^Y Key:GGXICVAJURFBLW-CEYXHVGTSA-N^Y

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye. This includes ocular hypertension and open angle glaucoma. It is applied as eye drops to the eyes. Onset of effects is usually within four hours, and they last for up to a day.

Common side effects include blurry vision, redness of the eye, itchiness, and darkening of the iris. Latanoprost is in the prostaglandin analogue family of medication. It works by increasing the outflow of aqueous fluid from the eyes through the uveoscleral tract.

Latanoprost approved for medical use in the United States in 1996. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Latanoprost is available as a generic medication. The wholesale cost in the developing world is about 0.69 to 3.79 USD per 2.5 ml bottle. In the United States a month of treatment costs less than 25 USD.

In people with ocular hypertension including open-angle glaucoma (IOP ≥21 mm Hg), treatment with latanoprost reduced IOP levels by 22 to 39% over 1 to 12 months’ treatment. Latanoprost was more effective than timolol 0.5% twice daily in 3 of 4 large (n = 163 to 267) randomised, double-blind trials. Latanoprost demonstrated a stable long-term IOP-lowering effect in 1- or 2-year continuations of these trials, with no sign of diminishing effect during prolonged treatment.

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