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17-phenyl trinor Prostaglandin F diethyl amide

Cayman Chemical Item Number 16823

17-p-PGF-NEt2; 17-phenyl trinor PGF diethyl amide; Bimatoprost diethyl amide

17-phenyl trinor Prostaglandin F2α diethyl amide

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Description

17-phenyl trinor Prostaglandin F diethyl amide (17-phenyl trinor PGF diethyl amide) is an analog of PGF in which the C-1 carboxyl group has been modified to an N-diethyl amide. PG esters have been shown to have ocular hypotensive activity.1 PG N-ethyl amides were recently introduced as alternative PG hypotensive prodrugs.2 Studies have shown that bovine and human corneal tissue converts the N-ethyl amides of various PGs to the free acids with a conversion efficiency of about 2.5 µg/g corneal tissue/hr.3 However, dialkyl amides such as 17-phenyl trinor PGF diethyl amide are inert to corneal amidase activity, and are not converted in any detectable amount to the corresponding free acids. These compounds may therefore be useful tools in elucidating the claim that PG amides have intrinsic intraocular hypotensive activity.

1 Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp Eye Res 38 181-184 (1984).

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

3 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).

Synonyms
  • 17-p-PGF2α-NEt2
  • 17-phenyl trinor PGF2α diethyl amide
  • Bimatoprost diethyl amide
Formal Name N-​diethyl-​9α,​11α,​15S-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prosta-​5Z,​13E-​dien-​1-​amide
Molecular Formula C27H41NO4
Formula Weight 443.6
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCN(CC)​C(=O)​CCC/C=C\CC1C(O)​CC(O)​[C@@H]​1\C=C\C(O)​CCc1ccccc1

Background Reading

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).

Maddox, Y.T., Ramwell, P.T., Shiner, C.S., et al. Amide and l-amino derivatives of F prostaglandins as prostaglandin antagonists. Nature 273 549-552 (1978).

Griffen, B.W., Klimko, P., Crider, J.Y., et al. AL-8810: A novel prostaglandin F analog with selective antagonist effects at the prostaglandin F (FP) receptor. J Pharmacol Exp Ther 290 1278-1284 (1999).

Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp Eye Res 38 181-184 (1984).

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

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17-phenyl trinor Prostaglandin F2α diethyl amide is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $46.00 $0.00
5 mg $207.00 $0.00
10 mg $368.00 $0.00
100 mg $2,760.00 $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 2012-05-26. 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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