An ocular hypotensive prodrug
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Prostaglandin F2α ethyl amide

Item No. 16016

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-ethyl-9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-amide
CAS Number
54130-36-8
Synonyms
  • Dinoprost ethyl amide
  • PGF2α-NEt
Molecular Formula
C22H39NO4
Formula Weight
381.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 16 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 300 µg/ml
SMILES
O[C@@H](CCCCC)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(N([H])CC)=O
InChi Code
InChI=1S/C22H39NO4/c1-3-5-8-11-17(24)14-15-19-18(20(25)16-21(19)26)12-9-6-7-10-13-22(27)23-4-2/h6,9,14-15,17-21,24-26H,3-5,7-8,10-13,16H2,1-2H3,(H,23,27)/b9-6-,15-14+/t17-,18+,19+,20-,21+/m0/s1
InChi Key
HLETUMXUCSCVPL-GWSKAPOCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Prostaglandin F2α ethyl amide (PGF2α-NEt) is an analog of PGF2α in which the C-1 carboxyl group has been modified to an N-ethyl amide. PG esters have been shown to have ocular hypotensive activity.1 PG N-ethyl amides were recently introduced as alternative prostaglandin ocular hypotensive prodrugs.2 Although it has been claimed that PG ethyl amides are not converted to the free acids in vivo, studies in our laboratories have shown that bovine and human corneal tissue converts the N-ethyl amides of various prostaglandins to the free acids with a conversion rate of about 2.5 µg/g corneal tissue/hr.2,3 PGF2α-NEt would be expected to show the typical intraocular effects of PGF2α free acid, but with the much slower hydrolysis pharmacokinetics of the PG N-amides.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp. Eye Res. 38(2), 181-184 (1984).

    2. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).

    3. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv. Ophthalmol. 47(Suppl. 1), S34-S40 (2002).