Chemical Property of Latanoprost
Chemical Property:
- Appearance/Colour:pale yellow oil
- Refractive Index:1.537
- Boiling Point:583.8 °C at 760 mmHg
- PKA:14.84±0.70(Predicted)
- Flash Point:188.3 °C
- PSA：86.99000
- Density:1.093 g/cm3
- LogP:4.18640
- Storage Temp.:−20°C
- Solubility.:DMSO: freely soluble
- Water Solubility.:DMSO: freely soluble
- XLogP3:4.3
- Hydrogen Bond Donor Count:3
- Hydrogen Bond Acceptor Count:5
- Rotatable Bond Count:14
- Exact Mass:432.28757437
- Heavy Atom Count:31
- Complexity:526
- Purity/Quality:
-
99%min *data from raw suppliers
Latanoprost *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
-
SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Canonical SMILES:CC(C)OC(=O)CCCC=CCC1C(CC(C1CCC(CCC2=CC=CC=C2)O)O)O
- Isomeric SMILES:CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
- Recent ClinicalTrials:Effect of Benzalkonium Chloride Preserved and Preservative-free Latanoprost Eye Drops on Conjunctival Goblet Cells
- Recent EU Clinical Trials:Non-inferiority, Randomized, Observer-blind, two Parallel Group, Clinical Trial for Comparing the Efficacy and Tolerability of a new Generic BAC-free Formulation of Latanoprost/Timolol 0.05 mg/mL + 5 mg/mL eye drops, solution in single-dose container vs Xalacom? eye drops, solution in Patients with Open Angle Glaucoma or Ocular Hypertension
- Recent NIPH Clinical Trials:Efficacy and Safety Study of 0.002% STN1013900 ophthalmic solution under concomitant use of Latanoprost ophthalmic solution 0.005% in subjects with primary open angle glaucoma or ocular hypertension
-
Uses
It can be used for the treatment of glaucoma. Prostanoid receptor ligand antifungal polyene macrolide that is active in the cell membrane soluble 5% Acetic acid Latanoprost 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. Prostaglandin analog, used to treat glaucoma and other degenerative diseases of the eye.
-
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.
-
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.
-
Therapeutic Function
Antiglaucoma
