LIPID MAPS

Prostaglandin E1 (PGE1) is a vasoactive prostaglandin and an active metabolite of dihomo-γ-linolenic acid (DGLA).^1,2 It is formed from DGLA by COX-1 and COX-2. PGE1 is an agonist of the PGE2 receptor subtypes EP1, EP2, EP3, and EP4, and the IP receptor (Kis = 36, 10, 1.1, 2.1, and 33 nM, respectively, for the mouse receptors).³ It inhibits ADP-induced platelet aggregation of isolated human platelet-rich plasma (IC50 = 40 nM) and isoproterenol-induced increases in L-type calcium current (ICa) in isolated rabbit atrial cells (EC50 = 27 nM).^4,5 PGE1 (100 nM) induces vasodilation in isolated rat aortic rings and activates ATP-sensitive potassium channels (KATP) in a cell-attached patch clamp assay using isolated rat vascular smooth muscle cells (VSMCs).¹ It decreases femoral arterial perfusion pressure in dogs.⁶ Formulations containing PGE1 have been used in the treatment of erectile dysfunction and to maintain patency of the ductus arteriosus in neonates with congenital heart defects who depend on a patent ductus arteriosus for survival.

This information has been provided by Cayman Chemical

References

1. Kobzar, G., Mardla, V., Järving, I., et al. Antiaggregating potency of E-type prostaglandins in human and rabbit platelets. Proc. Estonian Acad. Sci. Chem. 40(N3), 179-180 (1991).

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

3. 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).

4. Yamamoto, T., Habuchi, Y., Tanaka, H., et al. EP receptor-mediated inhibition by prostaglandin E1 or cardiac L-type Ca2+ current of rabbits. Am. J. Physiol. 277(4), H1369-H1374 (1999).

5. Levin, G., Duffin, K.L., Obukowicz, M.G., et al. Differential metabolism of dihomo-γ-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: Implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem. J. 365(Pt 2), 489-496 (2002).

6. Eguchi, S., Kawano, T., Yinhua, et al. Effects of prostaglandin E1 on vascular ATP-sensitive potassium channels. J. Cardiovasc. Pharmacol. 50(6), 686-691 (2007).

InChiKey (Click to copy)

GMVPRGQOIOIIMI-DWKJAMRDSA-N

InChi (Click to copy)

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O

Wikipedia

PGE1

KEGG ID

C04741

HMDB ID

HMDB0001442

CHEBI ID

15544

LIPIDBANK ID

XPR1400