MedKoo Biosciences

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

MedKoo CAT#: 591323

CAS#: 209860-88-8

Description: 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

Instruction

Theoretical Analysis

MedKoo Cat#: 591323
Name: Tafluprost acid
CAS#: 209860-88-8
Chemical Formula: C22H28F2O5
Exact Mass: 410.19
Molecular Weight: 410.460
Elemental Analysis: C, 64.38; H, 6.88; F, 9.26; O, 19.49

Price and Availability

Size	Price	Availability
5mg	USD 750	2 Weeks
10mg	USD 1350	2 Weeks
25mg	USD 2950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Product Data:

Product Data

Instruction:

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.460000000000000000000000000000 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

Molarity Calculator

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Reconstitution Calculator

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1: 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). pii: E217. doi: 10.3390/molecules22020217. PubMed PMID: 28146132. 2: 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. eCollection 2016. PubMed PMID: 27383260; PubMed Central PMCID: PMC4934872. 3: 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. PubMed PMID: 26391697. 4: 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. PubMed PMID: 26325164. 5: 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. PubMed PMID: 24508785. 6: Roh YJ, Park YG, Kang S, Kim SY, Moon JI. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch Clin Exp Ophthalmol. 2012 Dec;250(12):1765-75. doi: 10.1007/s00417-012-2125-2. Epub 2012 Aug 22. PubMed PMID: 22910791. 7: 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. Epub 2012 May 14. PubMed PMID: 22583577. 8: 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. PubMed PMID: 21791206. 9: 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. PubMed PMID: 21491995. 10: 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. PubMed PMID: 19477946. 11: 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. PubMed PMID: 19147999. 12: 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. PubMed PMID: 18752509. 13: Dong Y, Watabe H, Su G, Ishikawa H, Sato N, Yoshitomi T. Relaxing effect and mechanism of tafluprost on isolated rabbit ciliary arteries. Exp Eye Res. 2008 Sep;87(3):251-6. doi: 10.1016/j.exer.2008.06.005. Epub 2008 Jun 17. PubMed PMID: 18602392. 14: Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. PubMed PMID: 15037111. 15: Nakajima T, Matsugi T, Goto W, Kageyama M, Mori N, Matsumura Y, Hara H. New fluoroprostaglandin F(2alpha) derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull. 2003 Dec;26(12):1691-5. PubMed PMID: 14646172.

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