Product Name

Latanoprost

CAS Number

130209-82-4

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Product Name:
Latanoprost
CAS Number:
130209-82-4
Indication:
Latanoprost is used to reduce elevated intraocular pressure for patients diagnosed with open-angle glaucoma or ocular hypertension. The recommended dosage of Latanoprost is one drop in each affected eye daily, preferably in the evening. Treatment with Latanoprost should not exceed one drop daily, and it is not advisable for patients to use two more prostaglandin analogs concomitantly. A reduction of intraocular pressure is seen roughly 3 to 4 hours after dosing, with the maximum effect being reached by the 12 hour mark.
Mode of Action:

Latanoprost is a prostaglandin F2a analogue. Specifically, Latanoprost is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Thought of as a plumbing problem for the eye, Glaucoma is essentially when the drainage system of the eye is clogged. This clogging increases ocular pressure (IOP) and damages the optic nerve, leading to the diagnosis of glaucoma. If patients experience a prolonged period of time with elevated eye pressure they may have significant vision loss as a repercussion.

Pharmacodynamics:

Latanoprost is an isopropyl ester prodrug which is inactive but which becomes active after hydrolysis to the acid from. Latanoprost opthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.

Metabolism:

Primarily hepatic (none except hydrolysis in the eye). Latanoprost is an isopropyl ester prodrug. It is hydrolyzed by esterases in the cornea to latanoprost acid, which is biologically active. The portion of the latanoprost acid that reaches the systemic circulation is metabolized primarily by the liver to 1, 2-dinor and 1, 2, 3, 4-tetranor metabolites by fatty acid beta-oxidation.

Toxicity:

Between 5 and 15 percent of patients administered Latanoprost for six months or longer report at least one adverse effect from this drug. Common side effects reported include redness, blurry vision, burning, itching and stinging in the eye. Latanoprost may cause a long term change in the color of eyes, eyelids and eyelashes. These changes occur gradually and may be permanent.  

IUPAC:
propan-2-yl (5Z)-7-[(1R, 2R, 3R, 5S)-3, 5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
ATC:
S01EE01
PubChem:
5311221
DrugBank:
DB00654 (APRD01065)
Formula:
C26-H40-O5
Molecular Mass:
432.597
Synonyms:
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate, Latanoprost, PhXA 41, PHXA41, UNII-6Z5B6HVF6O, XA 41, XA41, Xalatan
SMILES:
CC(C)OC(=O)CCCC=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1
AHFS Code:
53:32.0
InChi:
GGXICVAJURFBLW-CEYXHVGTSA-N
Date Modified:
03-12-19
General Reference:
General Reference:

Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes]. Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [PubMed:11406947]

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