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Misoprostol (free acid)-d5

Cayman Chemical Item Number 10010333

Misoprostol (free acid)-d5

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Formal Name 9-​oxo-​11α,​16-​dihydroxy-​16-​(methyl-​d3)-​prost-​13E-​en-​1-​oic-​17,​17-​d2 acid
Molecular Formula C21H31D5O5
Formula Weight 371.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated product
Stability 1 year
Storage -20°C
Shipping Wet Ice in continental US; may vary elsewhere
SMILES CCCC([2H]​)​([2H]​)​C(O)​(C/C=C/[C@H]​1[C@H]​(O)​CC(=O)​[C@@H]​1CCCCCCC(=O)​O)​C([2H]​)​([2H]​)​[2H]​

Description

Misoprostol (free acid)-d5 contains five deuterium atoms at the 16 methyl, 17, and 17' positions. It is intended for use as an internal standard for the quantification of misoprostol (free acid) by GC- or LC-mass spectrometry (MS). 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 contains a C-1 methyl ester and 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., McGrath, J.C. Characterization of dilator prostanoid receptors in the fetal rabbit ductus arteriosus. J Pharmacol Exp Ther 271 390-396 (1994).

Related Articles

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

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).

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).

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

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Pricing updated 2010-09-02. Prices are subject to change without notice.

Pricing is for North America only. Other customers should contact a distributor in their region.

Cayman strives to be a reliable biochemical reagent vendor by providing the best possible products and services. 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.

Related Products

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Misoprostol (free acid)
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