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Sulprostone

Cayman Chemical Item Number 14765

(CAS 60325-46-4)

Sulprostone (CAS 60325-46-4)

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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

1 Schaaf, T.K., Bindra, J.S., Eggler, J.F., et al. N-(methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-selective, uterine stimulants. J Med Chem 24 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 285-293 (2000).

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

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

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

Formal Name N-​(methylsulfonyl)-​9-​oxo-​11α,​15R-​dihydroxy-​16-​phenoxy-​17,​18,​19,​20-​tetranor-​prosta-​5Z,​13E-​dien-​1-​amide
CAS Number 60325-46-4
Molecular Formula C23H31NO7S
Formula Weight 465.6
Formulation A solution in methyl acetate
Purity >98%
λmax 220, 270 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
OC(COc1ccccc1)​/C=C/[C@H]​1C(O)​CC(=O)​C1C/C=C\CCCC(=O)​NS(=O)​(=O)​C

Background Reading

Jumblatt, M.M., and Paterson, C.A. Prostaglandin E2 effects on corneal endothelial cyclic adenosine monophosphate synthesis and cell shape are mediated by a receptor of the EP2 subtype. Invest Ophthamol Vis Sci 32 360-365 (1991).

Smith, G.C.S., Coleman, R.A., and McGrath, J.C. Characterization of dilator prostanoid receptors in the fetal rabbit ductus arteriosus. J Pharmacol Exp Ther 271 390-396 (1994).

Toppozada, M., Warda, A., and Ramadan, M. Intramuscular 16-phenoxy PGE2 ester for pregnancy termination. Prostaglandins 17 461-467 (1979).

Strong, P., Coleman, R.A., and Humphrey, P.P.A. Prostanoid-induced inhibition of lipolysis in rat isolated adipocytes: Probable involvement of EP3 receptors. Prostaglandins 43 559-566 (1992).

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

De Vries, G.W., Guarino, P., McLaughlin, A., et al. An EP receptor with a novel pharmacological profile in the T-cell line Jurkat. Br J Pharmacol 115 1231-1234 (1995).

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

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

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

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 285-293 (2000).

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Sulprostone is available in the following screening libraries:

Size Price Quantity Subtotal
500 µg $45.00 $0.00
1 mg $86.00 $0.00
5 mg $360.00 $0.00
10 mg $630.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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