Latanoprost

Base Information

• Chemical Name: Latanoprost
• CAS No.: 130209-82-4
• Molecular Formula: C26H40O5
• Molecular Weight: 432.601
• Hs Code.: 2937500000
• European Community (EC) Number: 634-172-9
• UNII: 6Z5B6HVF6O,8S5FB3XXG8
• DSSTox Substance ID: DTXSID1041057
• Nikkaji Number: J458.015J
• Wikipedia: Latanoprost
• Wikidata: Q634959
• NCI Thesaurus Code: C29151
• RXCUI: 43611
• Pharos Ligand ID: 213UXXWMJBA2
• Metabolomics Workbench ID: 145392
• ChEMBL ID: CHEMBL1051
• Mol file: 130209-82-4.mol

Synonyms:latanoprost;PhXA34;PHXA41;Xalatan

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:

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

Technology Process of Latanoprost

There total 129 articles about Latanoprost which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.83%

2-iodo-propane (75-30-9) + latanoprost acid (41639-83-2) → isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate (145773-22-4,913258-34-1) + latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 14h;

DOI:10.1002/ejoc.200600749

Reference yield: 92.0%

latanoprost acid (41639-83-2) + isopropyl alcohol (67-63-0,8013-70-5) → latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With Lipase Novozym 435; at 30 ℃; for 18h; Enzymatic reaction;

Reference yield: 90.0%

isopropyl 11,15-bistetrahydropyranyloxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α → latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 52 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

2-iodo-propane

latanoprost acid

(-)-Corey lactone 5-(4-phenylbenzoate)

benzyl bromide

Refernces

• 1、 Kawauchi, Genki,Umemiya, Shigenobu,Taniguchi, Tohru,Monde, Kenji,Hayashi, Yujiro. "Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst". . p. 8409 - 8414. Retrieved 2018.
• 2、 Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er. "Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation". supporting information. p. 9923 - 9927. Retrieved 2019/05/16.