Analog of PGE2
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17-phenyl trinor Prostaglandin E2 ethyl amide

Item No. 13532

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-ethyl-9-oxo-11α,15S-dihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-amide
CAS Number
1219032-20-8
Synonyms
  • 17-phenyl trinor PGE2 ethyl amide
Molecular Formula
C25H35NO4
Formula Weight
413.6
Purity
≥98%
Formulation
A 5 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(NCC)=O)[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C25H35NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-22,24,27,29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,24+/m0/s1
InChi Key
XKYMIHJCJJUECW-XYOQMNIYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $104

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    5 mg

    $460

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    10 mg

    $813

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    Product Description

    17-phenyl trinor PGE2 ethyl amide is derived from 17-phenyl trinor PGE2, a synthetic analog of PGE2 that acts as an agonist of EP1 and EP3 receptors in mice (Ki = 14 and 3.7 nM, respectively) and EP1, EP3, and EP4 in rats (Ki = 25, 4.3, and 54 nM, respectively).1,2 17-phenyl trinor PGE2 causes contraction of guinea pig ileum at a concentration of 11 µM and is 4.4 times more potent than PGE2 as an antifertility agent in hamsters.3,4 Modification of the C-1 carboxyl group to an ethyl amide serves to increase lipid solubility, thereby improving uptake into tissues and further lowering the effective concentration. Ethyl amide groups are then removed by amidases, regenerating the active free acid.

    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. Boie, Y., Stocco, R., Sawyer, N., et al. Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes. Eur. J. Pharmacol. 340(2-3), 227-241 (1997).

    3. Lawrence, R.A., Jones, R.L., and Wilson, N.H. Characterization of receptors involved in the direct and indirect actions of prostaglandins E and I on the guinea-pig ileum. Br. J. Pharmacol. 105(2), 271-278 (1992).

    4. Miller, W.L., Weeks, J.R., Lauderdale, J.W., et al. Biological activities of 17-phenyl-18,19,20-trinorprostaglandins. Prostaglandins 9(1), 9-18 (1975).