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Misoprostol

Cayman Chemical Item Number 13820

SC-29333; Cytotec (CAS 59122-46-2)

Misoprostol (CAS 59122-46-2)

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Description

Misoprostol is a PGE1 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),2 inhibit superoxide generation in human neutrophils (EC50 = 0.35 µM),3 and relax fetal rabbit ductus arteriosus (EC50 = 0.36 nM)4 in a concentration dependent manner. Misoprostol is commonly used in clinical medicine for the prevention of peptic ulcer disease. It has also been used in conjunction with RU-486 for the oral induction of first trimester abortion. Misoprostol is readily absorbed and rapidly hydrolyzed in humans to the active free acid.1

1 Walt, R.P. Misoprostol for the treatment of peptic ulcer and antiinflammatory-drug-induced gastroduodenal ulceration. N Engl J Med 327 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 21 379-382 (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 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 271 390-396 (1994).

Synonyms
  • SC-29333
  • Cytotec
Formal Name 9-​oxo-​11α,​16-​dihydroxy-​16-​methyl-​prost-​13E-​en-​1-​oic acid,​ methyl ester
CAS Number 59122-46-2
Molecular Formula C22H38O5
Formula Weight 382.5
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC(C)​(O)​C/C=C/[C@H]​1C(O)​CC(=O)​C1CCCCCCC(=O)​OC

Background Reading

Audoly, L., and Breyer, R.M. The second extracellular loop of the prostaglandin EP3 receptor is an essential determinant of ligand selectivity. J Biol Chem 272 13475-13478 (1997).

Elliott, S.N., McKnight, W., Cirino, G., et al. A nitric oxide-releasing nonsteroidal anti-inflammatory drug accelerates gastric ulcer healing in rats. Gastroenterology 109 524-530 (1995).

Wallace, J.L., and Granger, D.N. Pathogenesis of NSAID gastropathy: Are neutrophils the culprits? Trends Pharmacol Sci 13 129-131 (1992).

Collins, P.W., Dajani, E.Z., Driskill, D.R., et al. Synthesis and gastric antisecretory properties of 15-deoxy-16-hydroxyprostaglandin E analogues. J Med Chem 20 1152-1159 (1977).

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

Honda, A., Sugimoto, Y., Namba, T., et al. Cloning and expression of a cDNA for mouse prostaglandin E receptor EP2T subtype. J Biol Chem 268 7759-7762 (1993).

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 1459-1465 (1995).

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 21 379-382 (1990).

Eglen, R.M., and Whiting, R.L. The action of prostanoid receptor agonists and antagonists on smooth muscle and platelets. Br J Pharmacol 94 591-601 (1988).

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 271 390-396 (1994).

Larsen, K.R., Jensen, N.F., Davis, E.K., et al. The cytroprotective effects of (+)-15-dexoy-16-α, β-hydroxy-16-methyl PGE1 methyl ester (SC-29333) versus aspirin-shock gastric ulcerogenesis in the dog. Prostaglandins 21 119-125 (1981).

Graham, D.Y., White, R.H., Moreland, L.W., et al. Duodenal and gastric ulcer prevention with misoprostol in arthritis patients taking NSAIDs. Ann Intern Med 119 257-262 (1993).

Zeng, L., An, S., and Goetzl, E.J. Selective regulation of RNK-16 cell matrix metalloproteinases by the EP4 subtype of prostaglandin E2 receptor. Biochemistry 35 7159-7164 (1996).

Collins, P.W. Misoprostol: Discovery, development, and clinical applications. Med Res Rev 10 149-172 (1990).

Zeng, L., An, S., and Goetzl, E.J. Regulation of expression of matrix metalloproteinase-9 in early human T cells of the HSB.2 cultured line by the EP3 subtype of prostaglandin E2 receptor. J Biol Chem 271 27744-27750 (1996).

Keith, R.H., Tsai, B.S., Collins, P.W., et al. Characterization of prostaglandin E receptors in canine small intestine using [3H] prostaglandin E1 binding. Prostaglandins 44 579-595 (1992).

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Misoprostol is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $11.00 $0.00
5 mg $50.00 $0.00
10 mg $88.00 $0.00
25 mg $193.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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8-iso Misoprostol Exclusive
Mifepristone
Misoprostol (free acid)
Prostaglandin E1
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