Arbaprostil | CAS# 55028-70-1 | Prodrug | Prostaglandin E Analog

MedKoo Cat#: 573222 | Name: Arbaprostil

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arbaprostil is a synthetic prostaglandin E analog that protects gastric mucosa, prevents ulceration, and promotes healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and can inhibit the growth of experimental tumors. Arbaprostil is a prodrug for the potent PGE2.

Chemical Structure

Arbaprostil

CAS#55028-70-1

Theoretical Analysis

MedKoo Cat#: 573222

Name: Arbaprostil

CAS#: 55028-70-1

Chemical Formula: C21H34O5

Exact Mass: 366.2406

Molecular Weight: 366.50

Elemental Analysis: C, 68.82; H, 9.35; O, 21.83

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 385.00	2 Weeks

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Related CAS #

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Synonym

Arbaprostil; 15(R)-15-methyl PGE2

IUPAC/Chemical Name

(E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3R)-(3-hydroxy-3-methyl-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid

InChi Key

XSGQFHNPNWBVPT-VFXMVCAWSA-N

InChi Code

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

SMILES Code

CCCCC[C@@](C)(O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 366.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Joseph Sister. Arbaprostil in bleeding peptic ulcer. Br Med J (Clin Res Ed). 1985 Dec 7;291(6509):1648. doi: 10.1136/bmj.291.6509.1648. PMID: 2934110; PMCID: PMC1418387. 2: Euler AR, Bailey RJ, Zinny MA, Brandon ML, Rousseau B, Ferguson JP, Wood DR, Le VH. Arbaprostil [15(R)-15-methyl prostaglandin E2] in a single nighttime dose of either 50 or 100 micrograms in acute duodenal ulcer. Gastroenterology. 1989 Jul;97(1):98-103. doi: 10.1016/0016-5085(89)91421-2. PMID: 2656368. 3: Hsyu PH, Cox JW, Pullen RH, Gee WL, Euler AR. Pharmacokinetic interactions between arbaprostil and aspirin in humans. Biopharm Drug Dispos. 1989 Jul- Aug;10(4):411-22. doi: 10.1002/bdd.2510100408. PMID: 2758104. 4: Vantrappen G, Janssens J, Popiela T, Kulig J, Tytgat GN, Huibregtse K, Lambert R, Pauchard JP, Robert A. Effect of 15(R)-15-methyl prostaglandin E2 (arbaprostil) on the healing of duodenal ulcer: a double-blind multicenter study. Gastroenterology. 1982 Aug;83(2):357-63. PMID: 7044880. 5: Thornburgh BA, Shaw SR, Wickrema Sinha AJ. Isolation and characterization of urinary metabolites of arbaprostil in the rat. Eur J Drug Metab Pharmacokinet. 1986 Jan-Mar;11(1):61-9. doi: 10.1007/BF03189776. PMID: 3720796. 6: Okabe S, Jino H, Nishida A. Effects of 15(R)-15-methyl prostaglandin E2 (arbaprostil) on gastric secretion and various gastric lesions induced in rats. Jpn J Pharmacol. 1986 Feb;40(2):329-37. doi: 10.1254/jjp.40.329. PMID: 3702150. 7: Takanashi H, Akima M. Protective effects of arbaprostil against indomethacin- induced gastric lesions in rats: significance of maintained gastric blood flow. Jpn J Pharmacol. 1992 Jul;59(3):349-55. doi: 10.1254/jjp.59.349. PMID: 1434129. 8: Lauritsen K, Laursen LS, Havelund T, Bytzer P, Rask-Madsen J. Controlled trial of arbaprostil in bleeding peptic ulcer. Br Med J (Clin Res Ed). 1985 Oct 19;291(6502):1093. doi: 10.1136/bmj.291.6502.1093. PMID: 3931810; PMCID: PMC1417007. 9: Sugiyama S, Kawabe Y, Kuroiwa M, Goto H, Tsukamoto Y, Ozawa T. Effects of the synthesized prostaglandin E2-analogue arbaprostil on gastric mucosal lesions in rats. Arzneimittelforschung. 1989 Dec;39(12):1571-3. PMID: 2624606. 10: Takanashi H, Kawabe Y, Akima M. Acid-promoted epimerization of arbaprostil, 15(R)-15-methylprostaglandin E2, elicits gastric antisecretory activities in rats. Jpn J Pharmacol. 1991 Dec;57(4):559-64. doi: 10.1254/jjp.57.559. PMID: 1803067. 11: Euler AR, Leodolter S, Huber J, Lookabaugh J, Burns MD, Phan TD, Wood DR, Bogaerts H, Kitt M. Arbaprostil's [15(R)-15-methyl PGE2] effects on intrauterine pressure in the nonpregnant and pregnant human female--a report of four clinical trials. Prostaglandins Leukot Essent Fatty Acids. 1989 Nov;38(2):91-8. doi: 10.1016/0952-3278(89)90091-4. PMID: 2694180. 12: Euler AR, Popiela T, Tytgat GN, Kulig J, Lookabaugh JL, Phan TD, Kitt MM. A multiclinic trial evaluating arbaprostil [15(R)-15-methyl prostaglandin E2] as a therapeutic agent for gastric ulcer. Gastroenterology. 1989 Apr;96(4):967-71. doi: 10.1016/0016-5085(89)91611-9. PMID: 2647578. 13: Li JY, Nagata T, Yoshida M, Yagi N, Katoh K, Haramoto T, Itoh K, Iwasaki A, Matsuo Y. Effect of 15(R)-15-methyl PGE2 (arbaprostil) on duodenal bicarbonate secretion in rat. Gastroenterol Jpn. 1989 Feb;24(1):8-11. doi: 10.1007/BF02774863. PMID: 2707555. 14: Euler AR, Safdi M, Rao J, Jaszewski R, Welsh J, Le V, Raskin J, Fleischmann R, Razzaque M, Champion C, et al. A report of three multiclinic trials evaluating arbaprostil in arthritic patients with ASA/NSAID gastric mucosal damage. The Upjohn Company Arbaprostil ASA/NSAID Gastric Mucosal Damage Treatment Study Groups. Gastroenterology. 1990 Jun;98(6):1549-57. doi: 10.1016/0016-5085(90)91089-o. PMID: 2186951. 15: Cox JW, Bothwell WM, Pullen RH, Wynalda MA, Fitzpatrick FA, VanderLugt JT. Plasma levels of the prodrug, arbaprostil, [(15R)-15-methylprostaglandin E2], and its active, antiulcer (15S) epimer in humans after single dose oral administration. J Pharm Sci. 1986 Nov;75(11):1107-12. doi: 10.1002/jps.2600751118. PMID: 3820107. 16: Euler AR, Krawiec J, Odes H, Gilat T, Garcia L, Rachmilewitz D, Gabryelewicz A, Gibinski K, Bass D, Barbara L, et al. An evaluation of arbaprostil at multiple doses for the treatment of acute duodenal ulcer: a randomized double- blind placebo-controlled international trial. Am J Gastroenterol. 1990 Feb;85(2):145-9. PMID: 2405642. 17: Euler AR, Tytgat G, Berenguer J, Brunner H, Wood DR, Lookabaugh JL, Phan TD. Failure of a cytoprotective dose of arbaprostil to heal acute duodenal ulcers. Results of a multiclinic trial. Gastroenterology. 1987 Mar;92(3):604-7. doi: 10.1016/0016-5085(87)90007-2. PMID: 3545965. 18: Thornburgh BA, Shaw SR, Bronson GE, Sinha AJ. Isolation and characterization of the urinary metabolites of arbaprostil in the male dog after intravenous administration. Eur J Drug Metab Pharmacokinet. 1988 Apr-Jun;13(2):113-21. doi: 10.1007/BF03191312. PMID: 3208790. 19: Reele SB, Euler AR, Hanover CK, Lookabaugh JL. Lack of effect of arbaprostil on the human non-pregnant uterus. Acta Obstet Gynecol Scand. 1985;64(8):645-7. doi: 10.3109/00016348509158206. PMID: 3914178. 20: Reele SB, Euler A, McEvers J, Metzler C. Arbaprostil (15(R)-15-methyl PGE2): lack of effect on theophylline metabolism. Br J Clin Pharmacol. 1986 Feb;21(2):239-41. doi: 10.1111/j.1365-2125.1986.tb05183.x. PMID: 3954940; PMCID: PMC1400902.