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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)

See more	Prostaglandins (513)

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	Copy SMILES to clipboard CCCCC[C@@](C)(O)\C=C\[C@H]1C(O)CC(=O)C1C/C=C\CCCC(=O)O

Background Reading

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).

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

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).

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

Karim, S.M.M., Carter, D.C., Bhana, D., et al. Effect of orally administered prostaglandin E₂ and its 15-methyl analogues on gastric secretion. Br Med J 1 143-146 (1973).

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

Size	Price	Quantity	Subtotal
1 mg	$54.00		$0.00
5 mg	$243.00		$0.00
10 mg	$432.00		$0.00
50 mg	$1,890.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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15(S)-15-methyl Prostaglandin E₂ Exclusive

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15(R)-15-methyl Prostaglandin E2