Prostaglandin F2α diethyl amide

Prostaglandin F_2α diethyl amide

Cayman Chemical Item Number 16023

Dinoprost diethyl amide; PGF_2α-NEt2

Description

Prostaglandin F_2α diethyl amide (PGF_2α-NEt2) is an analog of PGF_2α 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 in our laboratories 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 4 µg/g corneal tissue/hr.³ However, we find that dialkyl amides such as PGF_2α-NEt2 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

Dinoprost diethyl amide
PGF2α-NEt2

Formal Name

N,N-diethyl-9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-amide

Molecular Formula

C₂₄H₄₃NO₄

Formula Weight

409.6

Formulation

A solution in methyl acetate

Purity

>98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(N(CC)CC)=O

Background Reading

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

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).

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

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1 mg 
$38.00

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5 mg 
$171.00

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10 mg 
$304.00

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50 mg 
$1,330.00

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Prostaglandin F_2α diethyl amide