A PGE2 analog
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20-ethyl Prostaglandin E2

Item No. 14940

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-decen-1-yl]-5-oxocyclopentyl]-5-heptenoic acid
CAS Number
37492-24-3
Synonyms
  • 20-ethyl PGE2
Molecular Formula
C22H36O5
Formula Weight
380.5
Purity
≥97%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 125 µg/ml
SMILES
CCCCCCC[C@H](O)/C=C/[C@H]([C@H]1C/C=C\CCCC(O)=O)[C@H](O)CC1=O
InChi Code
InChI=1S/C22H36O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,14-15,17-19,21,23,25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)/b9-6-,15-14+/t17-,18+,19+,21+/m0/s1
InChi Key
NXMMZTNQIJBMBC-QKIVIXBWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $71

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    10 mg

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    Product Description

    20-ethyl Prostaglandin E2 (20-ethyl PGE2) is an analog of PGE2 in which the ω-chain has been extended by the addition of two methylene carbon atoms. The only well studied prostaglandin analog with this structural feature is unoprostone, an F-series prostaglandin that is clinically approved as a glaucoma medication.1 Unoprostone also contains lower side chain modifications (13,14-dihydro-15-keto) which severely limit its affinity for FP receptors, contributing to its lack of potency as a medication. 20-ethyl PGE2 retains the natural 15(S) allylic hydroxyl in the lower side chain, which may improve its potency relative to unoprostone. However, ligand binding assays of this analog with respect to EP or other prostanoid receptors have not been published. E-type prostaglandins have been widely reported to have inflammatory, cytoprotective, and a variety of other effects.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9(3), 213-218 (1996).

    2. Matsumoto, H., Naraba, H., Murakami, M., et al. Concordant induction of prostaglandin E2 synthase with cyclooxygenase-2 leads to preferred production of prostaglandin E2 over thromboxane and prostaglandin D2 in lipopolysaccharide-stimulated rat peritoneal macrophages. Biochem. Biophys. Res. Commun. 230(1), 110-114 (1997).

    3. Karim, S.M.M., Carter, D.C., Bhana, D., et al. Effect of orally administered prostaglandin E2 and its 15-methyl analogues on gastric secretion. Br. Med. J. 1(5846), 143-146 (1973).

    4. Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am. J. Obstet. Gynecol. 171(4), 1092-1096 (1994).