An EP2, EP3, and EP4 receptor agonist
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Labeled Version(s)
10010333Misoprostol (free acid)-d5
Metabolite(s)
22693tetranor-Misoprostol
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Misoprostol (free acid)

Item No. 13821

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11α,16-dihydroxy-16-methyl-9-oxo-prost-13E-en-1-oic acid
CAS Number
112137-89-0
Molecular Formula
C21H36O5
Formula Weight
368.5
Purity
≥97%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS (pH 7.2): 1.67 mg/ml
SMILES
O[C@H]1[C@H](/C=C/CC(C)(O)CCCC)[C@@H](CCCCCCC(O)=O)C(C1)=O
InChi Code
InChI=1S/C21H36O5/c1-3-4-13-21(2,26)14-9-11-17-16(18(22)15-19(17)23)10-7-5-6-8-12-20(24)25/h9,11,16-17,19,23,26H,3-8,10,12-15H2,1-2H3,(H,24,25)/b11-9+/t16-,17-,19-,21?/m1/s1
InChi Key
CNWGPXZGIIOYDL-MKYGPDKMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    50 mg

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    Product Description

    Misoprostol is a prostaglandin E1 (Item No. 13010) analog with agonist activity mediated by EP2, EP3, and EP4 receptors.1,2,3,4 It has been shown to inhibit the formation of gastric lesions in rats (ED50 = 0.31 µg/kg), inhibit superoxide generation in human neutrophils (EC50 = 0.35 µM), and relax fetal rabbit ductus arteriosus (EC50 = 0.36 nM) in a concentration dependent manner.2,3,4 Misoprostol is commonly used in clinical medicine for the prevention of peptic ulcer disease. It has also been used in conjunction with mifepristone (RU-486; Item No. 10006317) for the oral induction of first trimester abortion. Misoprostol contains a C-1 methyl ester and is readily absorbed and rapidly hydrolyzed in humans to the active free acid.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Walt, R.P. Misoprostol for the treatment of peptic ulcer and antiinflammatory-drug-induced gastroduodenal ulceration. N. Engl. J. Med. 327(22), 1575-1580 (1992).

    2. Bunce, K.T., Clayton, N.M., Coleman, R.A., et al. GR63799X - a novel prostanoid with selectivity for EP3 receptors. Adv. Prostaglandin Thromboxane Leukot. Res. 21(A), 379-382 (1990).

    3. Talpain, E., Armstrong, R.A., Coleman, R.A., et al. Characterization of the PGE receptor subtype mediating inhibition of superoxide production in human neutrophils. Br. J. Pharmacol. 114(7), 1459-1465 (1995).

    4. Smith, G.C.S., Coleman, R.A., and McGrath, J.C. Characterization of dilator prostanoid receptors in the fetal rabbit ductus arteriosus. J. Pharmacol. Exp. Ther. 271(1), 390-396 (1994).