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Tafluprost

CAS# 209860-87-7

Tafluprost

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Tafluprost

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Chemical Properties of Tafluprost

Cas No. 209860-87-7 SDF Download SDF
PubChem ID 6433101 Appearance Powder
Formula C25H34F2O5 M.Wt 452.53
Type of Compound N/A Storage Desiccate at -20°C
Synonyms AFP-168; MK2452
Solubility DMSO : ≥ 270 mg/mL (596.65 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name propan-2-yl (E)-7-[2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
SMILES CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC=C2)(F)F)O)O
Standard InChIKey WSNODXPBBALQOF-ZHDUIJGQSA-N
Standard InChI InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3+,15-14+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
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Preparing Stock Solutions of Tafluprost

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2098 mL 11.049 mL 22.098 mL 44.196 mL 55.245 mL
5 mM 0.442 mL 2.2098 mL 4.4196 mL 8.8392 mL 11.049 mL
10 mM 0.221 mL 1.1049 mL 2.2098 mL 4.4196 mL 5.5245 mL
50 mM 0.0442 mL 0.221 mL 0.442 mL 0.8839 mL 1.1049 mL
100 mM 0.0221 mL 0.1105 mL 0.221 mL 0.442 mL 0.5524 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Tafluprost

Tafluprost(AFP-168) is an anti-glaucoma prostaglandin (PG) analog. Target:Others Tafluprost showed significant IOP-lowering effects without any safety concerns in patients with various types of glaucoma and OH in daily clinical practice and tafluprost is highly effective in any therapeutic patterns [1]. Tafluprost with reduced BAK has potential as a superior antiglaucoma drug, not only for its IOP-lowering effect, but also for its good corneal safety profile [2]. Tafluprost single-use vials treatment was effective in reducing IOP over the 3 years of this study, but visual field performance worsened by 10.3%-13.8% in patients with normal-tension glaucoma. Safety was satisfactory [3].

References:
[1]. Kuwayama, Y. and A. Nomura, Prospective observational post-marketing study of tafluprost for glaucoma and ocular hypertension: short-term efficacy and safety. Adv Ther, 2014. 31(4): p. 461-71. [2]. Kumagami, T., et al., Comparison of corneal safety and intraocular pressure-lowering effect of tafluprost ophthalmic solution with other prostaglandin ophthalmic solutions. J Ocul Pharmacol Ther, 2014. 30(4): p. 340-5. [3]. Inoue, K., A. Tanaka, and G. Tomita, Effects of tafluprost treatment for 3 years in patients with normal-tension glaucoma. Clin Ophthalmol, 2013. 7: p. 1411-6.

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References on Tafluprost

24-Hour Efficacy and Ocular Surface Health with Preservative-Free Tafluprost Alone and in Conjunction with Preservative-Free Dorzolamide/Timolol Fixed Combination in Open-Angle Glaucoma Patients Insufficiently Controlled with Preserved Latanoprost Monotherapy.[Pubmed:27913991]

Adv Ther. 2017 Jan;34(1):221-235.

INTRODUCTION: The aim of the present study was to evaluate the 24-h efficacy, tolerability, and ocular surface health with preservative-free (PF) Tafluprost and a PF triple drug regimen comprising Tafluprost and dorzolamide/timolol fixed combination (DTFC) in open-angle glaucoma patients who were insufficiently controlled with preserved branded or generic latanoprost monotherapy and who exhibited signs or symptoms of ocular surface disease (OSD). METHODS: Prospective, observer-masked, crossover, comparison. Eligible consecutive open-angle glaucoma patients were randomized to either PF Tafluprost or the triple PF regimen for 3 months. They were then crossed over to the opposite therapy for another 3 months. At the end of the latanoprost run-in period and after each PF treatment period, patients underwent habitual 24-h intraocular pressure (IOP) monitoring with Goldmann tonometry in the sitting position (at 10:00, 14:00, 18:00, and 22:00) and Perkins tonometry in the supine position (at 02:00 and 06:00). Tolerability and selected ocular surface parameters were evaluated at baseline and the end of each treatment period. RESULTS: Forty-three open-angle glaucoma patients completed the trial. Mean 24-h IOP on preserved latanoprost was 22.2 +/- 3.9 mmHg. Compared with latanoprost monotherapy, PF Tafluprost obtained a greater reduction in mean, peak, and fluctuation of 24-h IOP including the 02:00 and 06:00 time points (P < 0.05). With the exception of 24-h fluctuation, the triple PF regimen provided significantly lower IOP parameters than latanoprost or PF Tafluprost (P < 0.001). Finally, PF Tafluprost therapy displayed significantly improved tear film break-up times (6.7 vs 6.0 s), corneal staining (1.3 vs 2.2), and Schirmer I test results (9.1 vs 8.2 mm) compared with the preserved latanoprost baseline (all P < 0.01). The triple PF regimen demonstrated similar tear film break-up times (6.1 vs 6.0 s) and Schirmer I test results (8.2 vs 8.2 mm) to latanoprost, but revealed a significant improvement in the corneal stain test (1.7 vs 2.2; P < 0.001). CONCLUSIONS: In this trial PF Tafluprost therapy provided statistically greater 24-h efficacy and improved tolerability compared with preserved latanoprost. The combination of PF Tafluprost and PF dorzolamide/timolol fixed combination was statistically and clinically more efficacious than both monotherapies and demonstrated similar ocular surface characteristics to preserved latanoprost monotherapy. TRIAL REGISTRATION: ClinicalTrials.gov (NCT02802137). FUNDING: Santen.

Analysis of the effects of preservative-free tafluprost on the tear proteome.[Pubmed:27829990]

Am J Transl Res. 2016 Oct 15;8(10):4025-4039. eCollection 2016.

The purpose of the present study was to assess the ocular surface health status in primary open angle glaucoma (POAG) patients switching from topical application of preserved latanoprost (LT) to preservative-free Tafluprost (PFT) by tear proteomic monitoring. Tear fluid of POAG patients showing dry eye symptoms, using LT and switching to PFT as well as tear fluid of healthy controls has been examined. Tear proteome dynamics was monitored over 24 weeks in a first mass spectrometric explorative analysis in a small POAG patient cohort (N = 3). Longitudinal responses of candidate proteins as well as cytokines were comparatively analyzed by microarray in a larger cohort of POAG patients (N = 16) and healthy controls (N = 15). Clinical parameters including tear breakup time (TBUT) and basal Schirmer test (BST) were recorded. Distinct post-switch level alterations could be documented in POAG tear proteins (> 1000). Cellular leakage proteins, dry eye related candidates and cytokines showed predominantly level diminishment in POAG patients and approximation to the tear protein level of healthy controls in response to PFT. Tear proteins like pyruvate kinase isozymes M1/M2 or galectin 7 displayed linear tear film level decline in POAG patients (R(2)>/=0.9; P < 0.05) distinctly converging the healthy level. Proteomic outcome fit well with improved clinical parameters, TBUT and BST. In conclusion, tear proteomic alterations indicated ocular surface recovery regarding epithelia leakage and inflammation recession. Together with improved clinical parameters the study output proposes beneficial effects of PFT glaucoma therapy.

A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost.[Pubmed:28146132]

Molecules. 2017 Jan 31;22(2). pii: molecules22020217.

Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2alpha (PGF2alpha) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to beta-blockers. A novel convergent synthesis of 5 was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde omega-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2alpha analogs 2-5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded Tafluprost (5). The main advantages are the preparation of high purity Tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other Tafluprost acid derivatives, Tafluprost methyl ester (32) and Tafluprost ethyl amide (33), are also described.

Comparison study of intraocular pressure reduction efficacy and safety between latanoprost and tafluprost in Japanese with normal-tension glaucoma.[Pubmed:27601879]

Clin Ophthalmol. 2016 Aug 24;10:1633-7.

PURPOSE: To evaluate and compare the intraocular pressure (IOP) reduction efficacy and safety between the ophthalmic solutions 0.005% latanoprost (Lat) and 0.0015% Tafluprost (Taf) in Japanese patients with normal-tension glaucoma (NTG). METHODS: In this randomized nonmasked study, we prospectively enrolled 30 Japanese NTG patients who had used Lat monotherapy for more than 4 weeks, and randomly divided them into the following two groups: 1) Lat-to-Taf group (LT group) and 2) Taf-to-Lat group (TL group). At the beginning of the study, both groups were switched from initial Lat to Lat or Taf for 12 weeks, and then switched over to the other drug (crossover) for 12 additional weeks. At 0, 4, 12, 16, and 24 weeks, we evaluated each patient's IOP, conjunctival injection, and corneal epitheliopathy score, and at 0, 12, and 24 weeks, we evaluated their eyelash changes and pigmentation of the eyelids and irises. RESULTS: The mean IOP of the LT group (15 eyes) was 10.5, 10.6, and 11.1 mmHg, at 0, 12, and 24 weeks, respectively, whereas that of the TL group (15 eyes) was 11.7, 11.1, and 10.5 mmHg at 0, 12, and 24 weeks, respectively. No significant differences were found between the two groups and in the intragroup comparisons. Moreover, no significant differences were found between Lat and Taf in regard to the conjunctival injection score and corneal epitheliopathy score. Eyelash changes and eyelid and iris pigmentation were similar in both groups. CONCLUSION: The findings of this study show that Lat and Taf have equivalent efficacy and safety in Japanese patients with NTG.

Description

Tafluprost(AFP-168) is an anti-glaucoma prostaglandin (PG) analog.

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