Latanoprost - CAS 130209-82-4
Catalog number:
Not Intended for Therapeutic Use. For research use only.
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Molecular Weight:
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.
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1. A versatile LC method for the simultaneous quantification of latanoprost, timolol and benzalkonium chloride and related substances in the presence of their degradation products in ophthalmic solution
Jigar Mehta, Vipul Patel, Nayan Kshatri and Niranjan Vyas*. Anal. Methods, 2010, 2, 1737–1744
As per the drug master files of latanoprost and timolol there are two known impurities of latanoprost: 1. Latanoprost acid (PhXA 85, (5Z,9a,11a,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oic acid) (major degradant in acid conditions) and, 2. 15-keto latanoprost (9a,11a-dihydroxy-15-oxo-17-phenyl-18,19,20-trinor-prost-5Z-en-1-oicacid, isopropyl ester). There is one known impurity of timolol: timolol impurity I, which was quantified and identified along with unknown impurities and preservative in the reported method. An extensive literature survey was carried out, which revealed that the said formulation is not official according to any pharmacopoeia, and only timolol maleate is officially a drug substance and individual formulation according to the Indian Pharmacopoeia, the British Pharmacopoeia10 and the US Pharmacopoeia. A few reports have been previously published regarding the determination of latanoprost by HPLC, the stability of latanoprost, the determination of BKC by HPLC and the determination of timolol by HPLC and NMR, voltammetric and HPTLC techniques. There is no method available for the simultaneous quantification of latanoprost, timolol and BKC in a formulation.
2. Gold catalysis in total synthesis—an update
Matthias Rudolph and A. Stephen K. Hashmi*. Chem. Soc. Rev., 2012, 41, 2448–2462
α,β-Unsaturated carbonyl compounds, usually addressed via classical condensation strategies or via Horner–Wadsworth–Emmons olefination, can alternatively be accessible via gold-catalysed Meyer–Schuster rearrangements. This concept was applied by Zanoni, Vidari and Nolan for the synthesis of various prostaglandins and their drug analogues (Scheme 10). Starting from commercially available Corey-lacton 19, the protected propargylic alcohol 20 was feasible in 2 steps. For the gold-catalysed step, a mixture of butanone/water and 5 equivalents of t-BuOH (to suppress desilylation) turned out to be essential for acceptable yields. Under these conditions enone 21 was gained in excellent yield with only 0.6 mol% of PPh3AuNTf2 in remarkable (E)-selectivity. Gold complexes with NHC ligands were also highly active and a free propargylic alcohol was tolerated in this case. From this key intermediate, three different prostaglandins were addressed by using classical prostaglandin chemistry. In the same contribution also the widely used anti-glaucoma PGF2a-like drugs Bimatoprost and Latanoprost were synthesized following the same strategy.
3. Amino acid and water-driven tunable green protocol to access S–S/C–S bonds via aerobic oxidative coupling and hydrothiolation
Amit Shard, Rajesh Kumar, Saima, Nidhi Sharmaa and Arun K. Sinha*. RSC Adv.,2014, 4, 33399–33407
Besides water, L-amino acids also dominate the natural world and display a central theme in biological systems. Recently, they have been efficiently employed as organocatalysts in triggering a variety of chemical reactions4 such as the synthesis of Pfizer's anti-glaucoma drug: latanoprost and the anticancer drug carboplatin. Interestingly, under physiological conditions, sulfur containing amino acids such as cysteine and glutathione, undergoes oxidative coupling to form the ubiquitous cystine and glutathione disulfide (GSSG) having disulfide (S-S) bonds which are of great practical value. Like-wise, an alicyclic disulfide known as lipoic acid also acts as an essential cofactor of mitochondrial enzymatic complexes which highlights the importance of the S–S bond. Some of the medicinally significant examples of disulfide bond are shown in Fig. 1.
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CAS 130209-82-4 Latanoprost

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