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209860-87-7 Usage


Tafluprost, also known as Taflotan, is a novel prostanoid used in the treatment of glaucoma. It is the first prostanoid to be released in a preservative-free formula and is effective in lowering intraocular pressure (IOP) by increasing uveoscleral outflow through agonism of the prostanoid FP receptor.


Used in Ophthalmology:
Tafluprost is used as a medication for the treatment of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. It helps in reducing the risk of blindness caused by glaucoma, which is the second most common cause of blindness after cataracts.
By 2010, it is estimated that approximately 60 million people worldwide will be afflicted by glaucoma, making effective treatments like Tafluprost essential for a large market. Compared to other prostaglandin analogs such as latanoprost, Tafluprost has a 10-fold greater affinity for the prostanoid FP receptor (Ki=0.4 nM), making it a more potent option for glaucoma treatment.
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.


Santen/Asahi Glass (Japan)


The synthesis was initiated from the Corey aldehyde 131. Horner-Emmons condensation of the bicyclic carbaldehyde 131 with the dimethyl phosphonate 132 using NaH in DMF gave enone 133 in 90% yield. Fluorination of the enone 133 was accomplished upon reaction with morpholino-sulfur trifluoride (134) in chloroform to yield the corresponding difluorinated compound 135. Hydrolysis of the benzoate ester group of 135 with K2CO3 in methanol at room temperature afforded alcohol 136 in 71% yield from 133. Reduction of the lactone group of 136 with diisobutyl aluminum hydride (DIBAL) in THF/toluene gave lactol 137 in 83% yield. Lactol 137 was condensed with the phosphonium ylide prepared by deprotonation of phosphonium salt 138 with sodium bis(trimethylsilyl)amide (NaHMDS) in THF/toluene to give the prostaglandin F2-alpha derivative 139 in excellent Z/E selectivity (99:1). The synthesis was completed by esterification of compound 139 with isopropyl iodide and DBU in acetone to provide tafluprost (XVIII) in 72% yield.

Check Digit Verification of cas no

The CAS Registry Mumber 209860-87-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,9,8,6 and 0 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 209860-87:
157 % 10 = 7
So 209860-87-7 is a valid CAS Registry Number.



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017


1.1 GHS Product identifier

Product name tafluprost

1.2 Other means of identification

Product number -
Other names Tafluprost

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:209860-87-7 SDS

209860-87-7Downstream Products

209860-87-7Relevant articles and documents

Synthesis of the highly potent prostanoid FP receptor agonist, AFP-168: A novel 15-deoxy-15,15-difluoroprostaglandin F2α derivative

Matsumura, Yasushi,Mori, Nobuaki,Nakano, Takashi,Sasakura, Hideshi,Matsugi, Takeshi,Hara, Hideaki,Morizawa, Yoshitomi

, p. 1527 - 1529 (2004)

A novel 15-deoxy-15,15-difluoro-prostaglandin(PG)F2α derivative 6 (AFP-168) has been synthesized from the Corey aldehyde in six steps. A key aspect of this route is difluorination of an enone and a stereoselective Wittig reaction. The compound shows high affinity to the FP receptor and potent activities for an anti-glaucoma agent.

Method for large-scale preparation of tafluprost


Paragraph 0019; 0027, (2021/01/24)

The invention discloses a method for industrially preparing tafluprost. The method comprises the following steps: taking Corey lactone as an initial raw material, oxidizing, condensing, fluorinating,deprotecting, reducing, re-condensing, esterifying and r

Crystal form of metallic salt compound of Tafluprost acid and preparation method of crystal form


, (2019/04/27)

The invention relates to a crystal form of a metallic salt compound of Tafluprost acid and a preparation method of the crystal form. Specifically, the invention relates to the crystal form of the metallic salt compound of Tafluprost acid, the preparation method of the crystal form and a method for preparing Tafluprost from the metallic salt compound of Tafluprost acid. According to the method, reaction yield is increased, isomer impurities are reduced, and the method is simple and easy to control and facilitates industrial expanded production.

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