| Identification | More | [Name]
Latanoprost | [CAS]
130209-82-4 | [Synonyms]
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
ISOPROPYL (5Z, 9A,11A,15R)-9,11,15-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OATE
LATANOPROST
XALATAN
(1r-(1-alpha(z),2-beta(r*),3-alpha,5-alpha))--methylethyleste
7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoicaci1
phxa41
xa41
isopropyl (5z,9α,11α,15r)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate
LATANAPROST
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, 1-methylethyl ester, (5Z)-(9CI)
5-Heptenoic acid, 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl]-, 1-methylethyl ester, [1R-[1a(Z),2b(R*),3a,5a]]-
Lata prostaglandin
Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)-cyclopentyl]hept-5-enoate
Xalatan, Isopropyl (5Z,9α,11α,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate
[1R-[1α(Z)，2β(R^<*>^)，3α，5α]]-7-[3，5-Dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)cyclopentyl]-5-heptenoic acid 1-methylethyl ester
Xalata | [EINECS(EC#)]
634-172-9 | [Molecular Formula]
C26H40O5 | [MDL Number]
MFCD00216074 | [Molecular Weight]
432.59 | [MOL File]
130209-82-4.mol |
| Questions And Answer | Back Directory | [a prostaglandin F2a analogue]
Latanoprost 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 solution]
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.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 effects]
Between 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 description]
Latanoprost 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 Structure]
Latanoprost 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 effects]
Topical 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 Properties]
It is a kind of colorless oil. [α] D20 + 31.57 ° (C = 0.91, acetonitrile).
| [Uses]
It can be used for the treatment of glaucoma.
| [Production method]
First 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 Properties | Back Directory | [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
| [pka]
14.84±0.70(Predicted) | [color ]
pale yellow
| [Merck ]
14,5376 | [BCS Class]
2 | [InChIKey]
GGXICVAJURFBLW-RDSJPUOVSA-N | [CAS DataBase Reference]
130209-82-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [WGK Germany ]
3
| [RTECS ]
MJ9669550
| [HS Code ]
2937500000 | [Safety Profile]
A poison by ingestion
and intravenous route. Human systemic
effects. When heated to decomposition it
emits acrid smoke and irritating vapors. |
| Hazard Information | Back Directory | [Description]
Xalatan 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. | [Originator]
Pharmacia & pjohn (UK) | [Definition]
ChEBI: 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 Process]
Manufacturing 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 name]
Xalatan (Pharmacia & Upjohn). | [Therapeutic Function]
Antiglaucoma | [General Description]
Latanoprost (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. | [Biochem/physiol Actions]
Latanoprost is a potent, selective prostaglandin F2α?analog receptor agonist. It is hydrolyzed by esterases into its biologically active form latanoprost acid in the cornea. Latanoprostplays a role in reducing the intraocular pressure (IOP) due to which it has therapeutic effects in treating glaucoma. | [storage]
Store at -20°C |
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