15(R)-Iloprost

• CAT Number: R042376
• CAS Number: 85026-51-3
• Molecular Formula: C22H32O4
• Molecular Weight: 360.5
• Purity: ≥95%
• Synonyms: 6,9α-methylene-11α,15R-dihydroxy-16-methyl-prosta-5E,13E-dien-18-yn-1-oic acid
• Storage: -20°C
• InChI: InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20-,21+/m0/s1
• InChIKey: HIFJCPQKFCZDDL-GAGQTBDJSA-N
• SMILES: O[C@H]1[C@H](/C=C/[C@H](O)C(C)CC#CC)[C@@H](C/C(C2)=C/CCCC(O)=O)[C@@H]2C1

Iloprost is a second generation structural analog of prostacyclin (PGI2) with about ten-<wbr></wbr>fold greater potency than the first generation stable analogs, typified by carbaprostacyclin. Iloprost binds with equal affinity to the recombinant human IP and EP receptors with a Ki of 11 nM. 15(R)-<wbr></wbr>Iloprost is the “unnatural” or inverted C-<wbr></wbr>15 epimer of iloprost. This transformation frequently attenuates the biological agonist activity of prostaglandin analogs by several orders of magnitude. There are no literature reports of the biological activity of 15(R)-<wbr></wbr>iloprost.

Reference

1.Schrör, K.,Darius, H.,Matzky, R., et al. The antiplatelet and cardiovascular actions of a new carbacyclin derivative (ZK36374) – equipotent to PGI2 in vitro. Naunyn-Schmiedeberg/’s Archives of Pharmacology 316, 252-255 (1981).