ChemicalBook > Product Catalog > API > Hormones and the Endocrine System > Prostaglandin drugs > 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 Safety Related Supplier
Latanoprost Chemical Properties
- alpha D20 +31.57° (c = 0.91 in acetonitrile)
- Boiling point:583.8±50.0 °C(Predicted)
- Density 1.093±0.06 g/cm3(Predicted)
- storage temp. −20°C
- solubility DMSO: freely soluble
- form oil
- color pale yellow
- Merck 14,5376
- CAS DataBase Reference130209-82-4(CAS DataBase Reference)
- WGK Germany 3
- RTECS MJ9669550
- HS Code 2937500000
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.
- DescriptionXalatan was launched in Sweden, Switzerland and the US for the treatment of glaucoma. It can be synthesized, from the Corey lactone, using standard prostaglandin chemistry. Latanoprost is a PGF2α, analog that is more lipophilic thus is better able to penetrate the cornea. The (15R)-diastereomer has only 10% of the activity compared to the (15S)-diastereomer. It is a selective FP receptor agonist with little or no effect on the other prostanoid receptors. The antiglaucoma effects are the result of reduced intraocular pressure arising by increasing uveoscleral outflow with little or no effect on trabeculo-canalicular aqueous outflow and no effect on retinal vasculation or permeability of the blood-aqueous barrier. The topical application is sufficient for a single daily dosage and is well tolerated with no detectible conjunctival hyperaemia.
- Chemical PropertiesLight Yellow Thick Oil
- OriginatorPharmacia & pjohn (UK)
- UsesProstanoid receptor ligand
- Usesantifungal polyene macrolide that is active in the cell membrane soluble 5% Acetic acid
- UsesLatanoprost is the isopropyl ester of 17-phenyl-13,14-dihydro prostaglandin F2α (17-phenyl-13,14-dihydro PGF2α). It is a prodrug form of the free acid, which is a potent agonist of the FP receptor in the eye. Latanoprost reduces intraocular pressure in glaucoma patients with few side effects. The EC50 value of latanoprost (tested as the free acid) for FP receptors is 3.6 nM.
- UsesProstaglandin analog, used to treat glaucoma and other degenerative diseases of the eye.
- DefinitionChEBI: A prostaglandin Falpha that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension.
- Manufacturing ProcessManufacturing process for Latanoprost includes these steps as follows: Synthesis of [3aR-[3aα,4α(E),5β,6aα]]-5-(benzoyloxy) hexahydro-4-(3-oxo-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]-5-(benzoyloxy)hexahydro- 4-(3 -hydroxy-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]- 5-(benzoyloxy)hexahydro-4-(3-hydroxy-5-phenyl-1-pentyl)-2Hcyclopenta[b]furan-2-one, synthesis of 2-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5- phenylpentyl]cyclopentyl]acetic acid, synthesis of [3aR-[3aα,4α(R),5β,6aα]]-hexahydro-5-hydroxy-4-(3-hydroxy-5- phenylpentyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4α(R),5β,6aα]]- hexahydro-5-hydroxy-4-(3-hydroxy-5-phenylpentyl)-2H-cyclopenta[b]furan-2-one;synthesis of (3aR,4R,5R,6aS)-5- (1-ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2Hcyclopenta[b]furan-2-ol;synthesis of 7-[(1R,2R,3R,5S)-3-(1-ethoxyethoxy)-5- hydroxy-2-[(3R)-3-(1-ethoxyethoxy)-5- phenylpentyl]cyclopentyl-5-heptenoic acid; synthesis of (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5- phenylpentyl]cyclopentyl]-5-heptenoic acid (Latanoprost Acid); At last, Latanoprost acid is dissolved in DMF (10 mL) and added to a slurry of cesium carbonate (1.6 g) in DMF (10 mL). 2-Iodopropane (0.49 mL) is added and the slurry is heated to 45°C for about 6 hours. When the reaction is complete, MTBE (40 mL) and water (50 mL) are added and the mixture is stirred for 15 min. The phases are separated and the aqueous phase is washed with MTBE (20 mL). The organic phases are combined and concentrated. The concentrate is chromatographed (silica gel) eluting with MTBE. The appropriate fractions are pooled and concentrated to give (5Z)-(9CI)-7-[(1R,2R,3R,5S)-3,5- Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl ]cyclopentyl]-5-heptenoic acid 1- methylethyl ester (Latanoprost).
- brand nameXalatan (Pharmacia & Upjohn).
- Therapeutic FunctionAntiglaucoma
- General DescriptionLatanoprost (Xalatan) is available as a 0.005% sterileophthalmic solution in a 2.5-mL dispenser bottle.Latanoprost is also marketed as a combination ophthalmicproduct with the β-adrenergic blocking agent, timolol,which apparently enhances IOP-lowering by decreasing theproduction of aqueous humor. Cautions and side effects aresimilar to those for other ophthalmic prostanoids.
- Safety ProfileA poison by ingestion and intravenous route. Human systemic effects. When heated to decomposition it emits acrid smoke and irritating vapors.
Latanoprost Preparation Products And Raw materials
- Travoprost Dorzolamide Hydrochloride LATANOPROST (FREE ACID),LATANOPROST ACID LATANOPROST LACTONE DIOL Latanoprost Epoxide (Mixture of isoMers) Latanoprost Impurity 1 Latanoprost Impurity (Diphenylphosphine Isopropyl Ester) Latanoprost Tris(triethylsilyl) Ether LATANOPROST LACTOL LATANOPROST ETHYL AMIDE 5-TRANS-LATANOPROST, [15-3H] LATANOPROST [15-3H] Latanoprost Bromocyclopentane Propane Solvent Red 43 Prostaglandin E2 PHENYL RESIN
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