What is the Tafluprost?

Tafluprost is , while it's Molecular Formula is C 25 H 34 F 2 O 5 . Tafluprost is a novel prostanoid used in the treatment of glaucoma and is the first prostanoid to be released in a preservative free-formula.

What is the CAS number for Tafluprost?

The CAS number of Tafluprost is 209860-87-7.

What is Tafluprost (209860-87-7) used for?

Glaucoma is second only to cataracts as a causative factor of blindness.By 2010, it is estimated that approximately 60 million people worldwidewill be afflicted by glaucoma, so effective treatments should garner a large market. PG analogs have been widely used for lowering IOP by increasing uveoscleral outflow through agonism of the prostanoid FPreceptor, and currently marketed versions include latanoprost, unoprostone isopropyl ester, bimatoprost, and travoprost. Compared to the carboxylic acid of latanaprost(Ki=4.7 nM), the carboxylic acid of tafluprost displayed a 10-fold greateraffinity for the prostanoid FP receptor (Ki=0.4 nM). The synthesis oftafluprost begins with a Wittig condensation of the protected bicycliclactone carbaldehyde with a dimethyl phosphonate ketone derivative.Compared to the carboxylic acid of latanaprost (Ki 4.7 nM), the carboxylic acid of tafluprost displayed a 10-fold greater affinity for the prostanoid FP receptor (Ki 0.4 nM). The synthesis of tafluprost begins with a Wittig condensation of the protected bicyclic lactone carbaldehyde with a dimethyl phosphonate ketone derivative. The bottom appendage is then completed by the fluorination of the ketone with morpholino-sulfur trifluoride. Hydrolysis of the benzoate ester protecting group liberates the hydroxy group, and reduction of the lactone is accomplished with aluminum hydride to generate the lactol. Condensation of this intermediate with the phosphonium salt of the acid side chain generates the free acid, or active ingredient, which is subsequently esterified with 2-iodopropane in the presence of DBU..InChI:InChI=1/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+

Product Class

209860-87-7

Product Name：Tafluprost
Molecular Formula：C₂₅H₃₄F₂O₅
Purity：99%
Molecular Weight：452.539

Inquiry

Product Details:

CasNo： 209860-87-7

Molecular Formula： C₂₅H₃₄F₂O₅

Buy High Purity 99% High Grade Tafluprost 209860-87-7 Safe Delivery

Molecular Formula:C₂₅H₃₄F₂O₅
Molecular Weight:452.539
Vapor Pressure:4.62E-13mmHg at 25°C
Refractive Index:1.548
Boiling Point:552.9ºC at 760mmHg
PKA:14.48±0.70(Predicted)
Flash Point:288.2°C
PSA：75.99000
Density:1.186 g/cm³
LogP:4.68300

Tafluprost(Cas 209860-87-7) Usage

Category	Prostaglandin Analog, Ophthalmic Medication
Definition	Tafluprost is a synthetic prostaglandin analogue primarily used in ophthalmology to reduce intraocular pressure (IOP) in patients with open-angle glaucoma and ocular hypertension. It works by acting as an agonist at prostaglandin F receptors, leading to increased aqueous humor outflow and, consequently, lower intraocular pressure.
Uses	Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Antibody-drug Conjugates (ADCs) and others. To maintain a high innovation efficiency, the company has continuously increased the investment on R&D facilities and state-of-the-art equipment in the past several years, including the establishment of kilogram GMP conditions plants and R&D centers. Tafluprost is used to treat open-angle glaucoma, the most common type of glaucoma, which occurs when the eye’s drainage canals become clogged, increasing IOP. It is also used to manage elevated intraocular pressure, a condition where the pressure in the eye is higher than normal, increasing the risk of glaucoma and vision loss.
Pharmacokinetics	Tafluprost is rapidly absorbed through the cornea, where it undergoes hydrolysis to the active form. About 75% of tafluprost is absorbed by the cornea after topical administration. It is metabolized by beta-oxidation and further oxidation, with a unique resistance to degradation due to its fluorine atoms.
Mechanism of Action	Once tafluprost penetrates the cornea, it is hydrolyzed by esterases to its active acid form, tafluprost acid, which has a high affinity for prostaglandin F receptors. By stimulating these receptors, it increases the outflow of aqueous humor from the eye, reducing IOP.
Brand name	Zioptan® (FDA Approved in 2012) Taflotan® (International Brand)
FDA Approval	Tafluprost, marketed under the brand name Zioptan, was approved by the FDA on February 10, 2012, for the treatment of glaucoma and ocular hypertension. It is available as an ophthalmic solution.

InChI:InChI=1/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+

209860-87-7 Relevant articles

Tafluprost once daily for treatment of elevated intraocular pressure in patients with open-angle glaucoma

Yang Liu &Weiming Mao

, Clinical Ophthalmology Volume 7, 2013 - Issue

Nakajima et al first reported the intraocular pressure-lowering effects of tafluprost in naïve experimental cynomolgus monkeys.Citation6 In that study one eye was treated with 20 μL of 0.0005% tafluprost or 0.005% latanoprost, while the fellow eye was treated with vehicle control. The authors found that treatment with tafluprost resulted in a significant intraocular pressure reduction of up to about 2 mmHg 4–8 hours following treatment, which was equivalent to the effect of latanoprost.

A Comparative, Placebo-Controlled Study of Prostanoid Fluoroprostaglandin-Receptor Agonists Tafluprost and Latanoprost in Healthy Males

Andrew Sutton, Anne Gilvarry, and Auli Ropo

Paragraph 0101-0103, (2021/05/29)

This was a phase I study in healthy males 18–45 years of age (N = 49). Participants were randomized to receive 1 of 4 eye drops: tafluprost 0.0025% or 0.005%, latanoprost 0.005%, or a placebo, administered once-daily for 7 days, with 1 drop per eye.

Tafluprost: The First Preservative-Free Prostaglandin to Treat Open-Angle Glaucoma and Ocular Hypertension

Cory Swymer and Michael W Neville

, Annals of pharmacotherapy, Volume 46, Issue 11,2012

Tafluprost 0.0015% is the first topical prostaglandin approved by the Food and Drug Administration for treatment of open-angle glaucoma and ocular hypertension that does not contain the widely used preservative, benzalkonium chloride (BAK). Although some controversy surrounds the long-term safety of exposure to BAK, clinical trial data are inconclusive.

209860-87-7 Process route

: 75-30-9
2-iodo-propane

: 209860-88-8
AFP-172

: 209860-87-7
tafluprost

Conditions

Conditions	Yield
AFP-172; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 0 ℃; Inert atmosphere; 2-iodo-propane; at 0 - 20 ℃; for 21h; Inert atmosphere;	83%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 5 - 30 ℃; Inert atmosphere;	82%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 16h;
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 16h;
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃;
With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Inert atmosphere;	6.8 g
With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Inert atmosphere;	6.8 g
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 22h;	9 mg
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 28 - 32 ℃; for 5h;	29.85 g

: (Z)-7-{(1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxy-cyclopentyl} hepta-5-enoic acid isopropyl ester

: 209860-87-7
tafluprost