15(R)-15-methyl Prostaglandin E2

Cayman Chemical Item Number 14725

Arbaprostil; 15(R)-15-methyl PGE2 (CAS 55028-70-1)

15(R)-15-methyl Prostaglandin E2 (CAS 55028-70-1)

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Description

15(R)-15-methyl PGE2 is a prodrug for the potent PGE2 analog 15(S)-15-methyl PGE2.1 Acid-catalyzed epimerization in the stomach produces the 15(S)-hydroxy compound which is biologically active.2 Oral administration of 15(R)-15-methyl PGE2 to dogs or rats at 10-300 µg/kg results in a dose-dependent inhibition of gastric acid secretion and an increase in the rate of duodenal bicarbonate secretion.3,4

1 Yankee, E.W., Axen, U., and Bundy, G.L. Total synthesis of 15-methylprostaglandins. J Am Chem Soc 96 5865-5876 (1974).

2 Takanashi, H., Kawabe, Y., and Akima, M. Acid-promoted epimerization of arbaprostil, 15(R)-15-methylprostaglandin E2, elicits gastric antisecretory activities in rats. Jpn J Pharmacol 57 559-564 (1991).

3 Takanashi, H., and Itoh, Z. Gastric antisecretory activity of 15(R)-15-methylprostaglandin E2, arbaprostil, in dogs. Jpn J Pharmacol 57 447-451 (1991).

4 Li, J., Nagata, T., Yoshida, M., et al. Effect of 15(R)-15-methyl PGE2 (arbaprostil) on duodenal bicarbonate secretion in rat. Gastroenerol Jpn 24 8-11 (1989).

Synonyms
  • Arbaprostil
  • 15(R)-15-methyl PGE2
Formal Name 9-​oxo-​11α,​15R-​dihydroxy-​15-​methyl-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 55028-70-1
Molecular Formula C21H34O5
Formula Weight 366.5
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O=C1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/[C@]​(C)​(O)​CCCCC)​[C@H]​(O)​C1
InCHI Code
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​1S/C21H34O5/c1-3-4-9-13-21(2,26)​14-12-17-16(18(22)​15-19(17)​23)​10-7-5-6-8-11-20(24)​25/h5,7,12,14,16-17,19,23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)​/b7-5-,14-12+/t16-,17-,19-,21-/m1/s1
InCHI Key
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XSGQFHNPNWBVPT-VFXMVCAWSA-N

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15(R)-15-methyl Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $59.00 $0.00
5 mg $266.00 $0.00
10 mg $472.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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