ChemicalBook--->CAS DataBase List--->209860-87-7

209860-87-7

209860-87-7 Structure

209860-87-7 Structure
IdentificationBack Directory
[Name]

Tafluprost
[CAS]

209860-87-7
[Synonyms]

TafL
uprost
MK2452
AFP-168
aflupros
TAFLUPROST
Tafluprosttrade
Tafluprost USP/EP/BP
209860-87-7 Tafluprost
He has fluprostaglandin
Isopropyl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoate
(Z)-Isopropyl 7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
15,15-DIFLUORO-9ALPHA,11ALPHA-DIHYDROXY-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER
(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
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)-
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)-
TafluprostQ: What is Tafluprost Q: What is the CAS Number of Tafluprost Q: What is the storage condition of Tafluprost Q: What are the applications of Tafluprost
[EINECS(EC#)]

234-199-2
[Molecular Formula]

C25H34F2O5
[MDL Number]

MFCD08062150
[MOL File]

209860-87-7.mol
[Molecular Weight]

452.53
Chemical PropertiesBack Directory
[Boiling point ]

552.9±50.0 °C(Predicted)
[density ]

1.186
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

soluble in Chloroform, DMSO, Ethyl Acetate
[form ]

Clear, colorless to slightly yellow oil
[pka]

14.48±0.70(Predicted)
Hazard InformationBack Directory
[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: Tafluprost(209860-87-7) is 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-chain 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. It has a role as a prostaglandin receptor agonist. It is a prostaglandins Falpha, an organofluorine compound and an isopropyl ester. It is functionally related to a prostaglandin F2alpha.
[Brand name]

Taflotan
[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.

Synthesis_209860-87-7

[storage]

Store at -20°C
[Mode of action]

Tafluprost(209860-87-7) is a Prostaglandin Analog. The mechanism of action of tafluprost is as a Prostaglandin Receptor Agonist. It is believed that prostanoid FP-receptor agonists such as tafluprost reduce IOP by increasing the uveoscleral outflow of aqueous humor. There is some evidence that tafluprost may lower IOP by interaction with the EP3 receptor.
DB08819
Spectrum DetailBack Directory
[Spectrum Detail]

Tafluprost(209860-87-7)1HNMR
209860-87-7 suppliers list
Company Name: airuikechemical co., ltd.
Tel: +undefined86-15315557071 , +undefined86-15315557071
Website: https://airuikechemical.com/
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: +86-0371-55170693 +86-19937530512 , +86-19937530512
Website: https://www.tianfuchem.com/
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008657128800458; +8615858145714 , +8615858145714
Website: http://www.fandachem.com
Company Name: Shanghai finete Pharmaceutical Co., Ltd.
Tel: +86-18221039705
Website: www.chemicalbook.com/ShowSupplierProductsList30566/0.htm
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
Website: www.atkchemical.com
Company Name: Shanghai Zheyan Biotech Co., Ltd.
Tel: 18017610038
Website: www.chemicalbook.com/ShowSupplierProductsList30845/0.htm
Company Name: career henan chemical co
Tel: +86-0371-86658258
Website: https://www.coreychem.com/
Company Name: Zhejiang ZETian Fine Chemicals Co. LTD
Tel: 18957127338 , 18957127338
Website: http://www.zetchem.com/
Company Name: Biochempartner
Tel: 0086-13720134139
Website: www.biochempartner.com
Company Name: Hubei Jusheng Technology Co.,Ltd.
Tel: 18871490254
Website: www.hubeijusheng.com
Company Name: HubeiwidelychemicaltechnologyCo.,Ltd
Tel: 18627774460
Website: www.chemicalbook.com/ShowSupplierProductsList1110588/0.htm
Company Name: Hubei xin bonus chemical co. LTD
Tel: 86-13657291602
Website: www.chemicalbook.com/ShowSupplierProductsList1549548/0.htm
Company Name: Shandong chuangyingchemical Co., Ltd.
Tel: 18853181302
Website: www.chemicalbook.com/ShowSupplierProductsList103425/0.htm
Company Name: BOC Sciences
Tel: +1-631-485-4226
Website: www.bocsci.com/
Company Name: Chongqing Chemdad Co., Ltd
Tel: +86-023-61398051 +8613650506873 , +8613650506873
Website: http://www.chemdad.com/
Company Name: CONIER CHEM AND PHARMA LIMITED
Tel: +8618523575427 , +8618523575427
Website: http://www.conier.com/
Company Name: Xi'an Yutbon Pharmaceutical Technology Co., Ltd
Tel: 029-81140587 +8618717328141 , +8618717328141
Website: http://www.yutbonpharma.com
Company Name: Zhengzhou Alfa Chemical Co.,Ltd
Tel: +8618530059196 , +8618530059196
Website: https://www.chemicalbook.com/manufacturer/zhengzhou-alfa-chemical-276/
Tags:209860-87-7 Related Product Information
157283-68-6 68291-97-4 130209-82-4 53179-13-8 274901-16-5 58579-51-4 119356-77-3 110-16-7 110-17-8 108-31-6 363-24-6 106-98-9