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(R)-Butaprost (free acid)
Cayman Chemical Item Number 10006045
Description
Butaprost is a structural analog of prostaglandin E2 (PGE2) with good selectivity for the EP2 receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells.1↗ Serious confusion as to the structure of butaprost was generated by Gardiner in 1986,2↗ when he reported that the epimer of butaprost showing this selective activity was the C-16 (R)-epimer (See reference 2 and NOTE). In order to increase the binding affinity of (R)-butaprost for prostanoid receptors, we removed the methyl ester of (R)-butaprost and re-established the natural C-1 carboxylic acid. Prostaglandin free acids generally bind to their cognate receptors with 10 to 100 times the affinity of the corresponding ester derivative. The pharmacology of (R)-butaprost has not been carefully studied, but it is generally considered to be the less active C-16 epimer.3↗ (NOTE: In the Gardiner paper in the 1986 British Journal of Pharmacology, butaprost appears on page 46 where it is given the name TR 4979. The structure as drawn is incorrect, in that the author was using and referring to the more active C-16 epimer, which is actually 16(S). The structure on page 46 shows the structure as 16(R). It was not until the late 1990’s that careful studies both in the US and Japan correctly identified the actual configuration of C-16 in the compound called butaprost is 16(S).)2↗
1 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 105 817-824 (1992).
2 Gardiner, P.J. Characterization of prostanoid relaxant/inhibitory receptors (XyX) using a highly selective agonist, TR4979. Br J Pharmacol 87 45-56 (1986).
3 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 46 213-220 (1994).
Synonyms (±)-15-deoxy-16R-hydroxy-17-cyclobutyl PGE1
15-deoxy-16R-hydroxy-17-cyclobutyl PGE1
Formal Name 9-oxo-11α,16R-dihydroxy-17-cyclobutyl-prost-13E-en-1-oic acid
CAS Number 215168-33-5
Molecular Formula C23H38O5
Formula Weight 394.6
Formulation A solution in methyl acetate
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES CCCC1(CCC1)[C@H](O)C/C=C/[C@H]1C(O)CC(=O)C1CCCCCCC(=O)O
InCHI Code 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-NMXQQJQMSA-N |