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Tafluprost

Tafluprost
Tafluprost structure
CAS No.
209860-87-7
Chemical Name:
Tafluprost
Synonyms
TafL;MK2452;uprost;AFP-168;aflupros;TAFLUPROST;209860-87-7;Tafluprost fandachem;Tafluprost USP/EP/BP;He has fluprostaglandin
CBNumber:
CB3401660
Molecular Formula:
C25H34F2O5
Formula Weight:
452.53
MOL File:
209860-87-7.mol

Tafluprost Properties

Boiling point:
552.9±50.0 °C(Predicted)
Density 
1.186
storage temp. 
Sealed in dry,2-8°C
pka
14.48±0.70(Predicted)
FDA UNII
1O6WQ6T7G3
ATC code
S01EE05

Tafluprost price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 10005440 Tafluprost ≥98% 209860-87-7 1mg $91 2021-03-22 Buy
Cayman Chemical 10005440 Tafluprost ≥98% 209860-87-7 5mg $410 2021-03-22 Buy
Cayman Chemical 10005440 Tafluprost ≥98% 209860-87-7 10mg $728 2021-03-22 Buy
Cayman Chemical 10005440 Tafluprost ≥98% 209860-87-7 25mg $1138 2021-03-22 Buy

Tafluprost Chemical Properties,Uses,Production

Description

Glaucoma is second only to cataracts as a causative factor of blindness. By 2010, it is estimated that approximately 60 million people worldwide will 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 FP receptor, 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 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.
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. .

Originator

Santen/Asahi Glass (Japan)

Uses

Tafluprost is a novel prostanoid used in the treatment of glaucoma and is the first prostanoid to be released in a preservative free-formula.

Definition

ChEBI: A prostaglandin Falpha that is prostaglandin F2alpha in which the carboxylic acid function has been converted to the corresponding isopropyl ester and the 3-hydroxy-1-octenyl side- hain is substituted by 3,3-difluoro-4-phenoxybut-1-enyl. Used for treatment of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

brand name

Taflotan

Chemical Synthesis

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.

Tafluprost Preparation Products And Raw materials

Raw materials

Preparation Products


Tafluprost Suppliers

Global( 175)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shanghai finete Pharmaceutical Co., Ltd.
+86-18221039705
- sales@finetechpharm.com CHINA 139 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8910 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26762 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Zhejiang ZETian Fine Chemicals Co. LTD
18957127338
stella@zetchem.com CHINA 2007 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58

View Lastest Price from Tafluprost manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-15 Tafluprost
209860-87-7
US $0.00 / KG 1KG 99% 200000pcs Hebei Yirun Sega Biological Technology Co. Ltd
2021-11-09 Tafluprost
209860-87-7
US $0.00 / Kg/Bag 2Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
2021-11-08 Tafluprost
209860-87-7
US $10.00 / KG 1KG 99% 20 tons Wuhan wingroup Pharmaceutical Co., Ltd

209860-87-7(Tafluprost)Related Search:


  • 209860-87-7
  • He has fluprostaglandin
  • TAFLUPROST
  • (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid 1-methylethyl ester
  • 15,15-DIFLUORO-9ALPHA,11ALPHA-DIHYDROXY-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER
  • AFP-168
  • Tafluprost5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-,1-methylethyl ester, (5Z)-
  • MK2452
  • TafL
  • uprost
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-
  • Tafluprost fandachem
  • aflupros
  • Tafluprost USP/EP/BP
  • 209860-87-7
  • 09860-87-7
  • C25H34F2O5
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