Selective EP3 receptor agonist
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Sulprostone

Item No. 14765

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl]-N-(methylsulfonyl)-5-heptenamide
CAS Number
60325-46-4
Molecular Formula
C23H31NO7S
Formula Weight
465.6
Purity
≥95%
Formulation (Request formulation change)
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >10 mg/mlDMSO: >14 mg/mlEthanol: >25 mg/mlPBS (pH 7.2): >4 mg/ml
λmax
220, 270 nm
SMILES
O=C1[C@H](C/C=C\CCCC(NS(=O)(C)=O)=O)[C@@H](/C=C/[C@@H](O)COC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/b7-2-,14-13+/t17-,19-,20-,22-/m1/s1
InChi Key
UQZVCDCIMBLVNR-TWYODKAFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $65

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    1 mg

    $124

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    5 mg

    $553

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    10 mg

    $974

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    Product Description

    Sulprostone is a metabolism resistant synthetic analog of PGE2.1 It is a selective agonist for EP3 receptors with a Ki value of 0.35 nM at the human recombinant EP3-III receptor and an IC50 of 0.01 µM for the inhibition of PGE2 binding.2,3 Sulprostone is a potent stimulator of uterine smooth muscle contractions with high abortifacient activity.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schaaf, T.K., Bindra, J.S., Eggler, J.F., et al. N-(methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-selective, uterine stimulants. J. Med. Chem. 24(11), 1353-1359 (1981).

    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(2), 285-293 (2000).

    3. Negishi, M., Harazono, A., Sugimoto, Y., et al. TEI-3356, a highly selective agonist for the prostaglandin EP3 receptor. Prostaglandins 48(5), 275-283 (1994).

    4. Schillinger, E., Prior, G., Speckenbach, A., et al. Receptor binding in various tissues of PGE2, and sulprostone, a novel PGE2-derivative. Prostaglandins 18(2), 293-302 (1979).

    5. Krishna, U., Gupta, A.N., Ma, H.K., et al. Randomized comparison of different prostaglandin analogues and laminaria tent for preoperative cervical dilation. Contraception 34(3), 237-251 (1986).

    Product Citations

    George, R.J., Sturmoski, M.A., Anant, S., et al. EP4 mediates PGE2 dependent cell survival through the PI3 kinase/AKT pathway. Prostaglandins Other Lipid Mediat. 83(1-2), 112-120 (2007).

    Herrerias, A., Torres, R., Serra, M., et al. Activity of the cyclooxygenase 2-prostaglandin-E prostanoid receptor pathway in mice exposed to house dust mite aeroallergens, and impact of exogenous prostaglandin E2. J. Inflamm. (Lond) 6, 30 (2009).