Taflpostamide
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MedKoo CAT#: 582048

CAS#: 1185851-52-8

Description: Taflpostamide, also known as Tafluprost ethyl amide, is derived from 17-phenyl trinor Prostaglandin F2α(17-phenyl trinor PGF2α). As a free acid, fafluprost is a very potent FP receptor agonist (Ki = 0.4 nM).6 Ethyl amides of PGs tend to increase lipid solubility, to improve uptake into tissues and to further lower the effective concentration. This product is supplied as a solution in ethanol (10mg/mL).

Chemical Structure

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Taflpostamide
CAS# 1185851-52-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 582048
Name: Taflpostamide
CAS#: 1185851-52-8
Chemical Formula: C24H33F2NO4
Exact Mass: 437.24
Molecular Weight: 437.528
Elemental Analysis: C, 65.88; H, 7.60; F, 8.68; N, 3.20; O, 14.63

Price and Availability

Size Price Availability Quantity
5mg USD 210 Ready to ship
10mg USD 350 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
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Related CAS #: 1185851-52-8    

Synonym: Taflpostamide; Dechloro; Dehydroxy; Difluoro; Ethylcloprostenolamide; Tafluprost ethyl amide.

IUPAC/Chemical Name: (Z)-7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)-N-ethylhept-5-enamide

InChi Key: VJZKLIPANASSBD-MSHHKXPZSA-N

InChi Code: InChI=1S/C24H33F2NO4/c1-2-27-23(30)13-9-4-3-8-12-19-20(22(29)16-21(19)28)14-15-24(25,26)17-31-18-10-6-5-7-11-18/h3,5-8,10-11,14-15,19-22,28-29H,2,4,9,12-13,16-17H2,1H3,(H,27,30)/b8-3-,15-14+/t19-,20-,21+,22-/m1/s1

SMILES Code: CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/C(COc2ccccc2)(F)F)O)O

Appearance: Oily liquid (sizes under 1g will be supplied in ethanol 10mg/mL)

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: >3 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:

Biological target: Tafluprost ethyl amide is a prostaglandin derivative. Tafluprost ethyl amide is capable of intraocular pressure (IOP) reduction and influencing eyelash growth. Tafluprost ethyl amide can be used in antiglaucoma ophthalmic compositions or cosmetics.
In vitro activity: As shown in Figure 9, tafluprost potently blocked TASK-1 outward currents in a concentration-dependent manner (EC50 = 186 ± 40 nM; Figures 9A,B). As the study reached 82% maximal inhibition, EC50 concentration corresponds to about 40% inhibition (not 50% inhibition). On the other hand, tafluprost also blocked NaV1.5 inward currents, although with much less potency than that observed at TASK-1 (estimated IC50 of about 76 µM Figure 9B). Reference: Front Pharmacol. 2022 Mar 18;13:855792. https://pubmed.ncbi.nlm.nih.gov/35370665/
In vivo activity: Conjunctival hyperemia, swelling and discharge in rabbit eye were all observed with both drug solutions and they appeared to peak at 30 minutes after the last instillation. By 5 hours, conjunctival hyperemia was essentially recovered with PF tafluprost opposite to PF latanoprost for which mild/moderate hyperemia was still widely seen. Reference: Open Ophthalmol J. 2016 May 31;10:146-53. https://pubmed.ncbi.nlm.nih.gov/27347250/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 68.57
DMF 30.0 68.57
Ethanol 30.0 68.57

Preparing Stock Solutions

The following data is based on the product molecular weight 437.53 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Valdés-Jiménez A, Jiménez-González D, Kiper AK, Rinné S, Decher N, González W, Reyes-Parada M, Núñez-Vivanco G. A New Strategy for Multitarget Drug Discovery/Repositioning Through the Identification of Similar 3D Amino Acid Patterns Among Proteins Structures: The Case of Tafluprost and its Effects on Cardiac Ion Channels. Front Pharmacol. 2022 Mar 18;13:855792. doi: 10.3389/fphar.2022.855792. PMID: 35370665; PMCID: PMC8971525. 2. Esaki Y, Shimazaki A, Pellinen P. Ocular Tolerability of Preservative-Free Tafluprost and Latanoprost: in vitro and in vivo Comparative Study. Open Ophthalmol J. 2016 May 31;10:146-53. doi: 10.2174/1874364101610010146. PMID: 27347250; PMCID: PMC4899509. 3. Pozarowska D. Safety and tolerability of tafluprost in treatment of elevated intraocular pressure in open-angle glaucoma and ocular hypertension. Clin Ophthalmol. 2010 Oct 21;4:1229-36. doi: 10.2147/OPTH.S6369. PMID: 21060677; PMCID: PMC2964963.
In vitro protocol: 1. Valdés-Jiménez A, Jiménez-González D, Kiper AK, Rinné S, Decher N, González W, Reyes-Parada M, Núñez-Vivanco G. A New Strategy for Multitarget Drug Discovery/Repositioning Through the Identification of Similar 3D Amino Acid Patterns Among Proteins Structures: The Case of Tafluprost and its Effects on Cardiac Ion Channels. Front Pharmacol. 2022 Mar 18;13:855792. doi: 10.3389/fphar.2022.855792. PMID: 35370665; PMCID: PMC8971525.
In vivo protocol: 1. Esaki Y, Shimazaki A, Pellinen P. Ocular Tolerability of Preservative-Free Tafluprost and Latanoprost: in vitro and in vivo Comparative Study. Open Ophthalmol J. 2016 May 31;10:146-53. doi: 10.2174/1874364101610010146. PMID: 27347250; PMCID: PMC4899509. 2. Pozarowska D. Safety and tolerability of tafluprost in treatment of elevated intraocular pressure in open-angle glaucoma and ocular hypertension. Clin Ophthalmol. 2010 Oct 21;4:1229-36. doi: 10.2147/OPTH.S6369. PMID: 21060677; PMCID: PMC2964963.

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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; PubMed Central PMCID: PMC6155834.