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Latanoprost

Catalog No. DB00654 Name DrugBank
CAS Number 130209-82-4 Website http://www.ualberta.ca/
M. F. C26H40O5 Telephone (780) 492-3111
M. W. 432.5928 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 536

SYNONYMS

IUPAC name
propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
IUPAC Traditional name
latanaprost
Brand Name
Xalatan Fixed Flow Device
Xalatan
Synonyms
latanoprost

DATABASE IDS

CAS Number 130209-82-4

PROPERTIES

Hydrophobicity(logP) 4.4
Solubility 8 mg/mL

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description Latanoprost 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 that works by increasing the outflow of aqueous fluid from the eyes.

It is also known by the brand name of Xalatan manufactured by Pfizer.
Indication For the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Pharmacology 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.
Toxicity Symptoms of overdose include bloodshot eyes and eye irritation.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Latanoprost is well absorbed through the cornea where the isopropyl ester prodrug is hydrolyzed to the acid form. Peak concentration is reached 2 hrs after topical administration.
Half Life 17 minutes
Clearance * 7 mL/min/kg
References
Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes] Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
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REFERENCES

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