Tafluprost acid | CAS#209860-88-8 | prostaglandin F receptor agonist

MedKoo Cat#: 591323 | Name: Tafluprost acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tafluprost acid is a selective agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eyes and thus lowering intraocular pressure. This product is supplied as a solution in methyl acetate.

Chemical Structure

Tafluprost acid

CAS#209860-88-8

Theoretical Analysis

MedKoo Cat#: 591323

Name: Tafluprost acid

CAS#: 209860-88-8

Chemical Formula: C22H28F2O5

Exact Mass: 410.1905

Molecular Weight: 410.46

Elemental Analysis: C, 64.38; H, 6.88; F, 9.26; O, 19.49

Price and Availability

Size	Price	Availability
5mg	USD 750.00	2 Weeks
10mg	USD 1,350.00	2 Weeks
25mg	USD 2,950.00	2 Weeks

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Related CAS #

No Data

Synonym

Tafluprost acid; UNII-WTV8EPZ396;

IUPAC/Chemical Name

5-Heptenoic acid, 7-((1R,2R,3R,5S)-2-((1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl)-3,5-dihydroxycyclopentyl)-, (5Z)-

InChi Key

KIQXRQVVYTYYAZ-VKVYFNERSA-N

InChi Code

InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+/t17-,18-,19+,20-/m1/s1

SMILES Code

O=C(O)CCC/C=C\C[C@@H]1[C@@H](/C=C/C(F)(F)COC2=CC=CC=C2)[C@H](O)C[C@@H]1O

Appearance

liquid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Uusitalo H, Kaarniranta K, Ropo A. Pharmacokinetics, efficacy and safety profiles of preserved and preservative-free tafluprost in healthy volunteers. Acta Ophthalmol Suppl (Oxf ). 2008;242:7-13. doi: 10.1111/j.1755-3768.2008.01380.x. PMID: 18752509. 2: Pellinen P, Lokkila J. Corneal penetration into rabbit aqueous humor is comparable between preserved and preservative-free tafluprost. Ophthalmic Res. 2009;41(2):118-22. doi: 10.1159/000192082. Epub 2009 Jan 16. PMID: 19147999. 3: Fukano Y, Kawazu K. Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. Drug Metab Dispos. 2009 Aug;37(8):1622-34. doi: 10.1124/dmd.108.024885. Epub 2009 May 28. PMID: 19477946. 4: Fukano Y, Kawazu K, Akaishi T, Bezwada P, Pellinen P. Metabolism and ocular tissue distribution of an antiglaucoma prostanoid, tafluprost, after ocular instillation to monkeys. J Ocul Pharmacol Ther. 2011 Jun;27(3):251-9. doi: 10.1089/jop.2010.0178. Epub 2011 Apr 14. PMID: 21491995. 5: Yamagishi R, Aihara M, Araie M. Neuroprotective effects of prostaglandin analogues on retinal ganglion cell death independent of intraocular pressure reduction. Exp Eye Res. 2011 Sep;93(3):265-70. doi: 10.1016/j.exer.2011.06.022. Epub 2011 Jul 26. PMID: 21791206. 6: Fukano Y, Tsuyama N, Mizuno H, Date S, Takano M, Masujima T. Drug metabolite heterogeneity in cultured single cells profiled by pico-trapping direct mass spectrometry. Nanomedicine (Lond). 2012 Sep;7(9):1365-74. doi: 10.2217/nnm.12.34. Epub 2012 May 14. PMID: 22583577. 7: Taketani Y, Yamagishi R, Fujishiro T, Igarashi M, Sakata R, Aihara M. Activation of the prostanoid FP receptor inhibits adipogenesis leading to deepening of the upper eyelid sulcus in prostaglandin-associated periorbitopathy. Invest Ophthalmol Vis Sci. 2014 Mar 4;55(3):1269-76. doi: 10.1167/iovs.13-12589. PMID: 24508785. 8: Akaishi T, Shimazaki A, Tonouchi A, Ueda K, Miyawaki N, Kawazu K. Benefits of Tafluprost and Timolol Fixed-Dose Combination for the Treatment of Glaucoma Are Confirmed by Studies on Experimental Animal Models. J Ocul Pharmacol Ther. 2015 Nov;31(9):518-24. doi: 10.1089/jop.2015.0031. Epub 2015 Sep 1. PMID: 26325164. 9: Kaarniranta K, Ikäheimo K, Mannermaa E, Ropo A. Pharmacokinetics, Efficacy, and Safety of the Preservative-free Fixed Combination of Tafluprost 0.0015% and Timolol 0.5% in Healthy Volunteers: A Phase I Comparison vs. the Corresponding Preservative-free Monotherapies. Clin Pharmacokinet. 2016 Apr;55(4):485-94. doi: 10.1007/s40262-015-0331-x. PMID: 26391697. 10: Fuwa M, Ueda K, Akaishi T, Yamashita N, Kirihara T, Shimazaki A, Mano H, Kawazu K. Advantages of Efficacy and Safety of Fixed-Dose Tafluprost/Timolol Combination Over Fixed-Dose Latanoprost/Timolol Combination. PLoS One. 2016 Jul 6;11(7):e0158797. doi: 10.1371/journal.pone.0158797. PMID: 27383260; PMCID: PMC4934872. 11: Krupa M, Chodyński M, Ostaszewska A, Cmoch P, Dams I. A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost. Molecules. 2017 Jan 31;22(2):217. doi: 10.3390/molecules22020217. PMID: 28146132; PMCID: PMC6155834. 12: Sato K, Nakagawa Y, Omodaka K, Asada H, Fujii S, Masaki K, Nakazawa T. The Sustained Release of Tafluprost with a Drug Delivery System Prevents the Axonal Injury-induced Loss of Retinal Ganglion Cells in Rats. Curr Eye Res. 2020 Sep;45(9):1114-1123. doi: 10.1080/02713683.2020.1715446. Epub 2020 Jan 29. PMID: 31994948.