A vasoactive prostaglandin and an active metabolite of DGLA
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Prostaglandin E1

Item No. 13010

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11α,15S-dihydroxy-9-oxo-prost-13E-en-1-oic acid
CAS Number
745-65-3
Synonyms
  • Alprostadil
  • NSC 165559
  • PGE1
Molecular Formula
C20H34O5
Formula Weight
354.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.5 mg/ml
SMILES
O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
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
InChi Key
GMVPRGQOIOIIMI-DWKJAMRDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Prostaglandin E1 (PGE1) is a vasoactive prostaglandin and an active metabolite of dihomo-γ-linolenic acid (DGLA; Item No. 90230).1,2 It is formed from DGLA by COX-1 and COX-2. PGE1 is an agonist of the PGE2 (Item No. 14010) 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    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. 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).

    5. 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).

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

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Hiyama, H., Arichika, N., Okada, M., et al. Pharmacological profile of difamilast, a novel selective phosphodiesterase 4 inhibitor, for topical treatment of atopic dermatitis. J. Pharmacol. Exp. Ther. 386(1), 45-55 (2023).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Schröder, R., Xue, L., Konya, V., et al. PGH1, the precursor for the anti-inflammatory prostaglandins of the 1-series, is a potent activator of the pro-inflammatory receptor CRTH2/DP2. PLoS One 7(3), e33329 (2012).