A potent luteolytic and smooth muscle contractor
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Prostaglandin F2α

Item No. 16010

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid
CAS Number
551-11-1
Synonyms
  • Dinoprost
  • PGF2α
Molecular Formula
C20H34O5
Formula Weight
354.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChi Key
PXGPLTODNUVGFL-YNNPMVKQSA-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 F2α (PGF2α) is a widely distributed PG occurring in many species.1,2,3 It causes contraction of vascular, bronchial, intestinal, and myometrial smooth muscle, and also exhibits potent luteolytic activity.2 PGF2α exerts its receptor mediated physiological activity at 50-100 nM.2 Maximal ovine myometrial contraction can be achieved at 125 nM PGF2α in vitro.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Speroff, L., and Ramwell, P.W. Prostaglandins in reproductive physiology. Am. J. Obstet. Gynecol. 107(7), 1111-1130 (1970).

    2. Samuelsson, B., Goldyne, M., Granström, E., et al. Prostaglandins and thromboxanes. Annu. Rev. Biochem. 47, 997-1029 (1978).

    3. Watanabe, K., Iguchi, Y., Iguchi, S., et al. Stereospecific conversion of prostaglandin D2 to (5Z,13E)-(15S)-9α,-11β,15-trihydroxyprosta-5,13-dien-1-oic acid (9α,11β-prostaglandin F2) and of prostaglandin H2 to prostaglandin F2α by bovine lung prostaglandin F synthase. Proc. Natl. Acad. Sci. USA 83(6), 1583-1587 (1986).

    4. Crankshaw, D.J., and Gaspar, V. Pharmacological characterization in vitro of prostanoid receptors in the myometrium of nonpregnant ewes. J. Reprod. Fertil. 103(1), 55-61 (1995).

    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).

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    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).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Schmidleithner, L., Thabet, Y., Schönfeld, E., et al. Enzymatic activity of HPGD in Treg cells suppresses Tconv cells to maintain adipose tissue homeostasis and prevent metabolic dysfunction. Immunity 50(5), 1232-1248 (2019).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Skiba, D.S., Nosalski, R., Mikolajczyk, T.P., et al. Anti-atherosclerotic effect of the angiotensin 1-7 mimetic AVE0991 is mediated by inhibition of perivascular and plaque inflammation in early atherosclerosis. Br. J. Pharmacol. 174(22), 4055-4069 (2017).

    Fuchikami, C., Murakami, K., Tajima, K., et al. A comparison of vasodilation mode among selexipag (NS-304; [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide]), its active metabolite MRE-269 and various prostacyclin receptor agonists in rat, porcine and human pulmonary arteries. Eur. J. Pharmacol. 795, 75-83 (2017).

    Suganami, A., Fujino, H., Okura, I., et al. Human DP and EP2 prostanoid receptors take on distinct forms depending on the diverse binding of different ligands. FEBS J. 283(21), 3931-3940 (2016).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Pharmacological characterization of a novel antiglaucoma agent, bimatoprost (AGN 192024). J. Pharmacol. Exp. Ther. 305(2), 772-785 (2003).

    Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).

    Sakairi, Y., Jacobson, H.R., Noland, T.D., et al. 5,6-EET inhibits ion transport in collecting duct by stimulating endogenous prostaglandin synthesis. Am. J. Physiol. 268(5 Pt 2), F931-F939 (1995).