An EP2-selective prostaglandin E2 analog
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Butaprost (free acid)

Item No. 13741

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
CAS Number
433219-55-7
Synonyms
  • (±)-15-deoxy-16S-hydroxy-17-cyclobutyl PGE1
  • 15-deoxy-16S-hydroxy-17-cyclobutyl PGE1
Molecular Formula
C23H38O5
Formula Weight
394.6
Purity
≥95%
Formulation
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25/mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
CCCC1(CCC1)[C@@H](O)C/C=C/[C@H]([C@H]2CCCCCCC(O)=O)[C@H](O)CC2=O
InChi Code
InChI=1S/C23H38O5/c1-2-13-23(14-8-15-23)21(26)11-7-10-18-17(19(24)16-20(18)25)9-5-3-4-6-12-22(27)28/h7,10,17-18,20-21,25-26H,2-6,8-9,11-16H2,1H3,(H,27,28)/b10-7+/t17-,18-,20-,21+/m1/s1
InChi Key
PAYNQYXOKJDXAV-ZHIWTBQHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $120

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    1 mg

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    5 mg

    $960

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    10 mg

    $1,559

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    Product Description

    Butaprost is an EP2 selective agonist which has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells.1,2 Prostaglandin free acids generally bind to their cognate receptors with 10 to 100 times the affinity of the corresponding ester derivative. Consistent with this trend, butaprost binds to membranes from EP2 receptor-transfected CHO cells with a Ki value of 2,400 nM, whereas butaprost (free acid) and CAY10399 (the 2-series congener of butaprost free acid) exhibit significantly lower Ki values of 73 and 92 nM, respectively.3 Butaprost (free acid) is therefore another useful tool for characterizing EP receptor-mediated signaling events.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    3. Tani, K., Naganawa, A., Ishida, A., et al. Design and synthesis of a highly selective EP2-receptor agonist. Bioorg. Med. Chem. Lett. 11(15), 2025-2028 (2001).