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Latanoprost

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Latanoprost Basic information
a prostaglandin F2a analogue Latanoprost ophthalmic solution Side effects Product description Molecular Structure Adverse reactions and side effects Chemical Properties Uses Production method
Product Name:Latanoprost
Synonyms:XALATAN;ISOPROPYL (5Z, 9A,11A,15R)-9,11,15-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OATE;LATANOPROST;17-PHENYL-13,14-DIHYDRO TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER;9ALPHA,11ALPHA,15R-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OIC ACID, ISOPROPYL ESTER;9ALPHA, 11ALPHA, 15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROS-5Z-EN-1-OIC ACID, ISOPROPYL ESTER;(1r-(1-alpha(z),2-beta(r*),3-alpha,5-alpha))--methylethyleste;7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoicaci1
CAS:130209-82-4
MF:C26H40O5
MW:432.59
EINECS:
Product Categories:Active Pharmaceutical Ingredients;Prostaglandins;Prostaglandin;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Other APIs;Inhibitors;Key Products
Mol File:130209-82-4.mol
Latanoprost Structure
Latanoprost Chemical Properties
storage temp. −20°C
solubility DMSO: freely soluble
form oil
color pale yellow
CAS DataBase Reference130209-82-4(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS MJ9669550
MSDS Information
ProviderLanguage
SigmaAldrich English
Latanoprost Usage And Synthesis
a prostaglandin F2a analogueLatanoprost is a prostaglandin F2a analogue.It is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor.
It is used to treat certain kinds of glaucoma(open-angle glaucoma ocular hypertension). It is also used to treat a condition called hypertension of the eye. Latanoprost is used to increase the natural outflow of fluid (aqueous humor) from inside the eye into the bloodstream. It appears to work by increasing the outflow of fluid from the eye. This lowers the pressure in the eye.
Latanoprost may make your eyesight blurred for a short length of time. if this happens do not drive or operate machine or use any tools until your eye sight becomes clear again.
Latanoprost ophthalmic solutionLatanoprost 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.For the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Latanoprost ophthalmic solution contain a preservative called benzalkonium chloride which can be absorbed onto the surface of contact lenses and may discolour soft contact lenses.
Side effectsBetween 6% and 10% (between 1 in 20 and 1 in 6) of persons receiving latanoprost for 6 months report at least one side effect localized to the eyes. These side effects included Temporary blurred vision after application, eyelid redness, permanently darken eyelashes,Swelling or erosions of the cornea,a sensation of a foreign body, discoloration of the iris, itching, a temporary burning sensation during use, and stinging. Discoloration of the iris begins happens slowly. It is caused by an increase in the amount of brown pigment in the iris and may be permanent. Other side effects which have been reported less frequently include dryness of the eyes, increased tearing, herpes simplex keratitis, eye pain and other eye-related discomfort.
Product descriptionLatanoprost is a novel anti-glaucoma drugs which is suitable for the treatment of primary open-angle glaucoma or the tropical treatment of patients of ocular hypertension which is difficult to be treated and tolerated. It also has excellent efficacy in treating pigment dispersion glaucoma, angle recession, chronic angle-closure glaucoma, uveitis and quiescent exfoliation syndrome but is invalid for treating of uveitis in its active stage.
Latanoprost is a kind of prostaglandin F2α derivative and is a kind of selective F2α receptor agonist. It is a non-active substance but can quickly penetrate into the cornea. It can be hydrolyzed into active free acid in the cornea and the plasma. It can increase the outflow amount of aqueous chambers water through the corner keratin layer. It only needs a small dose has a significant effect in boosting the outflow amount of the aqueous chambers water. The drug liquid can penetrate into the eyeball eyelashes suprachoroidal with excellent intraocular pressure lowering effect. Glaucoma will also clear the clogged trabecular mesh of patients.
Molecular StructureLatanoprost contains a pentene ring which has α- and ω-carbon chain with the ester of the α-carbon chain termini in the structure can facilitate its penetration through the cornea. At the corneal stroma, latanoprost can be decomposed into free acid which can bind to the FP receptor as the active part. It has hydroxyl group in C15, and has a short ω- chain and a benzene ring which are important for the efficacy of the drug.
Adverse reactions and side effectsTopical administration can result in mild to moderate conjunctival or scleral hyperemia.
Occasionally slight redness on eyes can be observed.
During the treatment of the first 2-3 days, the eyes will have a slight foreign body sensation; a small number of patients may get rash.
Chemical PropertiesIt is a kind of colorless oil. [α] D20 + 31.57 ° (C = 0.91, acetonitrile).
UsesIt can be used for the treatment of glaucoma.
Production methodFirst dissolve the compound (Ⅰ) in toluene, cool to 18 °C, further add dicyclohexyl carbodiimide (DCC) and phosphoric acid, followed by addition of (4-phenyl-3-oxobutyl) triphenylphosphonium iodide with condensation being converted to compound (II) which is further converted to the product through the six-step reaction.
Chemical PropertiesLight Yellow Thick Oil
UsageProstanoid receptor ligand
Usageantifungal polyene macrolide that is active in the cell membrane soluble 5% Acetic acid
UsageProstaglandin analog, used to treat glaucoma and other degenerative diseases of the eye.
Tag:Latanoprost(130209-82-4) Related Product Information
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