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Tafluprost

Cayman Chemical Item Number 10005440

AFP-168 (CAS 209860-87-7)

Tafluprost (CAS 209860-87-7)

See more	Receptor Biochemistry (344) Prostaglandins (517) Receptor Agonist (161) Ophthalmology (64)

Description

A number of 17-phenyl trinor Prostaglandin F_2α (17-phenyl trinor PGF_2α) derivatives have been approved for the treatment of glaucoma.^1,2,3,4 Of these, the ones wherein the 13,14-double bond has been hydrogenated retain relatively good potency, but show a significantly reduced incidence of local irritant side effects.⁵ Alternatively, it was recently reported that analogs incorporating a 15-deoxy-15,15-difluoro modification also had a favorable ophthalmic activity profile.⁶ Tafluprost is a 2-series, 16-phenoxy analog of PGF_2α with the 15,15-difluoro substitution. Tafluprost free acid is a very potent FP receptor agonist, with a K_i of 0.4 nM.⁶ The ester prodrug forms of tafluprost are also potent ocular hypotensives in monkeys.

1 Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of Bimatoprost (Lumigan^™). Surv Ophthalmol 45 S337-S345 (2001).

2 Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

3 Sorbera, L.A., and Castañer, J. Travoprost. Drugs Future 25 41-45 (2000).

4 Maxey, K.M., Johnson, J., Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol 47(4) 34-40 (2002).

5 Resul, B., Stjernschantz, J., No, K., et al. Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J Med Chem 36 243-248 (1993).

6 Nakajima, T., Matsugi, T., Goto, W., et al. New fluoroprostaglandin F_2α derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull 26(12) 1691-1695 (2003).

Synonyms	AFP-168
Formal Name	15,15-difluoro-9α,11α-dihydroxy-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic acid, isopropyl ester
CAS Number	209860-87-7
Molecular Formula	C₂₅H₃₄F₂O₅
Formula Weight	452.5
Formulation	A solution in methyl acetate
Purity	>98%
λ_max	269 nm
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CC(C)OC(=O)CCC/C=C\CC1C(O)CC(O)C1/C=C/C(F)(F)COc1ccccc1

Background Reading

Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of Bimatoprost (Lumigan^™). Surv Ophthalmol 45 S337-S345 (2001).

Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

Sorbera, L.A., and Castañer, J. Travoprost. Drugs Future 25 41-45 (2000).

Resul, B., Stjernschantz, J., No, K., et al. Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J Med Chem 36 243-248 (1993).

Nakajima, T., Matsugi, T., Goto, W., et al. New fluoroprostaglandin F_2α derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull 26(12) 1691-1695 (2003).

Maxey, K.M., Johnson, J., Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol 47(4) 34-40 (2002).

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Tafluprost is available in the following screening libraries:

Size	Price	Quantity	Subtotal
1 mg	$83.00		$0.00
5 mg	$374.00		$0.00
10 mg	$664.00		$0.00
25 mg	$1,453.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

16-phenoxy tetranor Prostaglandin F_2α

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17-phenyl trinor Prostaglandin F_2α isopropyl ester

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Fluprostenol isopropyl ester

Latanoprost

Latanoprost (free acid)

Prostaglandin F_2α

Tafluprost ethyl amide New

Tafluprost ethyl ester New Exclusive

Tafluprost (free acid)

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