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15(R)-Prostaglandin E₁

Cayman Chemical Item Number 13710

15-epi PGE₁; 15(R)-PGE₁ (CAS 20897-91-0)

15(R)-Prostaglandin E1 (CAS 20897-91-0)

See more	Prostaglandins (517)

Description

15(R)-PGE₁ is the “unnatural” C-15 stereoisomer of PGE₁. It is essentially inactive biologically when compared to PGE₁.¹ It is a non-competitive inhibitor of 15-hydroxy PGDH with an IC₅₀ of 189 µM.²

1 Nakano, J. Relationship between the chemical structure of prostaglandins and their vasoactivities in dogs. Br J Pharmacol 44 63-70 (1972).

2 Jarabak, J., and Braithwaite, S.S. Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placenta. The reaction mechanism and the mechanism of action of various inhibitors.. Arch Biochem Biophys 177 245-254 (1976).

Synonyms	15-epi PGE1 15(R)-PGE1
Formal Name	9-oxo-11α,15R-dihydroxy-prost-13E-en-1-oic acid
CAS Number	20897-91-0
Molecular Formula	C₂₀H₃₄O₅
Formula Weight	354.5
Formulation	A solution in methyl acetate
Purity	>98%
Stability	1 year
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCC[C@@H](O)/C=C/[C@H]1C(O)CC(=O)C1CCCCCCC(=O)O

Background Reading

Oien, H.G., Mandel, L.R., Humes, J.L., et al. Structural requirements for the binding of prostaglandins. Prostaglandins 9 985-995 (1975).

Murakami, A., and Akahori, Y. Conformational analysis of prostaglandins. III. Study on active sites and conformation-action relationship. Chem Pharm Bull 25 3155-3162 (1977).

Andersen, N.H. Dehydration of prostaglandins: Study by spectroscopic method. J Lipid Res 10 320-325 (1969).

Jarabak, J., and Braithwaite, S.S. Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placenta. The reaction mechanism and the mechanism of action of various inhibitors.. Arch Biochem Biophys 177 245-254 (1976).

Murakami, A., and Akahori, Y. Conformational analysis of prostaglandins. IV. Relationship between melting point and calculated conformational energy of prostaglandins. Chem Pharm Bull 27 548-550 (1979).

Lincoln, F.H., Schneider, W.P., and Pike, J.E. Prostanoic acid chemistry. II. Hydrogenation studies and preparation of 11-deoxyprostaglandins. J Org Chem 38 951-956 (1973).

Murakami, A., and Akahori, Y. Conformational analysis of prostaglandins. II. Most probable conformation of prostaglandin A, B, E, and F. Chem Pharm Bull 25 2870-2874 (1977).

Zoutendam, P.H., Bowman, P.B., Ryan, T.M., et al. Quantitative determination of alprostadil (PGE₁) in bulk drug and pharmaceutical formulations by high-performance liquid chromatography. J Chromatogr 283 273-280 (1984).

Rigaud, M., Breton, J.C., Gualde, N., et al. In vitro inhibition of human lymphocyte transformation by natural or synthetic prostaglandins. Prostaglandins Med 3 167-172 (1979).

Nakano, J. Relationship between the chemical structure of prostaglandins and their vasoactivities in dogs. Br J Pharmacol 44 63-70 (1972).

Beddell, C.R., and Goodford, P.J. Symmetry in prostaglandins. Prostaglandins 13 493-502 (1977).

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15(R)-Prostaglandin E1 is available in the following screening libraries:

Size	Price	Quantity	Subtotal
1 mg	$46.00		$0.00
5 mg	$207.00		$0.00
10 mg	$368.00		$0.00
50 mg	$1,610.00		$0.00
Bulk	Contact
		Cart Total	$0.00

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.

Related Products

13,14-dihydro-15(R)-Prostaglandin E₁

15(R),19(R)-hydroxy Prostaglandin E₁

CAY10397

Prostaglandin E₁

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15(R)-Prostaglandin E1