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Tafluprost (free acid)

Cayman Chemical Item Number 10005439

AFP-172 (CAS 209860-88-8)

Tafluprost (free acid) (CAS 209860-88-8)

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Description

A number of 17-phenyl trinor prostaglandin F2α (17-phenyl trinor PGF2α) 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 PGF2α with the 15,15-difluoro substitution. Tafluprost (free acid) is a very potent FP receptor agonist, with a Ki 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 Takagi, Y., Nakajima, T., Shimazaki, A., et al. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res 78 767-776 (2004).

Synonyms
  • AFP-172
Formal Name 9α,​11α-​dihydroxy-​15,​15-​difluoro-​16-​phenoxy-​17,​18,​19,​20-​tetranor-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 209860-88-8
Molecular Formula C22H28F2O5
Formula Weight 410.5
Formulation A solution in methyl acetate
Purity >98%
λmax 269, 276 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​(C[C@@H]​(O)​[C@@H]​1/C=C/C(F)​(F)​COC2=CC=CC=C2)​[C@@H]​1C/C=C\CCCC(O)​=O

Background Reading

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).

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

Takagi, Y., Nakajima, T., Shimazaki, A., et al. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res 78 767-776 (2004).

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).

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

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

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Tafluprost (free acid) is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $93.00 $0.00
5 mg $412.00 $0.00
10 mg $744.00 $0.00
50 mg $3,255.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

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.

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