A selective agonist for the EP2 receptors
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Butaprost

Item No. 13740

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11α,16S-dihydroxy-17-cyclobutyl-prost-13E-en-1-oic acid, methyl ester
CAS Number
69685-22-9
Synonyms
  • 15-deoxy-16S-hydroxy-17-cyclobutyl PGE1 methyl ester
  • TR 4979
Molecular Formula
C24H40O5
Formula Weight
408.6
Purity
≥98%
Formulation
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2)(1:3): .15 mg/ml
SMILES
O=C1[C@H](CCCCCCC(OC)=O)[C@@H](/C=C/C[C@H](O)C2(CCC2)CCC)C(O)C1
InChi Code
InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21?,22+/m1/s1
InChi Key
XRISENIKJUKIHD-KHAOJFLNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $99

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    1 mg

    $188

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    5 mg

    $693

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    10 mg

    $1,188

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    Product Description

    Butaprost, a structural analog of PGE2, is a selective agonist for the EP2 receptor subtype. EP2 receptors are expressed on human neutrophils and on respiratory, vascular, and uterine smooth muscle.1,2 Butaprost binds with about 1/10 the affinity of PGE2 to the recombinant murine EP2 receptor, and does not bind appreciably to any of the other murine EP receptors or DP, TP, FP, or IP receptors.3 The EC50 for the stimulation of cAMP by butaprost in COS cells transfected with the human EP2 receptor is about 5 µM, while the EC50 for PGE2 in this assay is about 43 nM.1 Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Regan, J.W., Bailey, T.J., Pepperl, D.J., et al. Cloning of a novel human prostaglandin receptor with characteristics of the pharmacologically defined EP2 subtype. Mol. Pharmacol. 46(2), 213-220 (1994).

    2. Talpain, E., Armstrong, R.A., Coleman, R.A., et al. Characterization of the PGE receptor subtype mediating inhibition of superoxide production in human neutrophils. Br. J. Pharmacol. 114(7), 1459-1465 (1995).

    3. Kiriyama, M., Ushikubi, F., Kobayashi, T., et al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br. J. Pharmacol. 122(2), 217-224 (1997).

    4. Lawrence, R.A., and Jones, R.L. Investigation of the prostaglandin E (EP-) receptor subtype mediating relaxation of the rabbit jugular vein. Br. J. Pharmacol. 105(4), 817-824 (1992).

    Product Citations

    Allain, E.P., Rouleau, M., Le, T., et al. In activation of prostaglandin E2 as a mechanism for UGT2B17-mediated adverse effects in chronic lymphocytic leukemia. Front. Oncol. 9:606, (2019).

    Lejeune, M., Moreau, F., and Chadee, K. Loss of EP2 receptor subtype in colonic cells compromise epithelial barrier integrity by altering claudin-4. PLoS One 9(11), e113270 (2014).

    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).