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MedKoo Cat#: 461341 | Name: Rioprostil

Description:

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

Rioprostil is a synthetic methylprostaglandin E1 analog that reduces gastric acid secretion and enhances the gastric mucus-bicarbonate barrier. It is effective in the therapy of gastric ulcers and gives significant protection against NSAID-induced gastric mucosal damage. The drug also prevents cyclosporin A-induced damage to endocrine and exocrine pancreatic secretions. It shows a low order of acute toxicity and there is no evidence of embryotoxicity, fetotoxicity, teratogenicity, or mutagenicity in animal studies.

Chemical Structure

Rioprostil
Rioprostil
CAS#77287-05-9

Theoretical Analysis

MedKoo Cat#: 461341

Name: Rioprostil

CAS#: 77287-05-9

Chemical Formula: C21H38O4

Exact Mass: 354.2770

Molecular Weight: 354.53

Elemental Analysis: C, 71.14; H, 10.80; O, 18.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rioprostil; Rioprostilum; TR-4698; TR 4698; TR4698;
IUPAC/Chemical Name
(2R,3R,4R)-4-hydroxy-3-((E)-4-hydroxy-4-methyloct-1-en-1-yl)-2-(7-hydroxyheptyl)cyclopentan-1-one
InChi Key
SPOAFZKFCYREMW-FWYLUGOYSA-N
InChi Code
InChI=1S/C21H38O4/c1-3-4-13-21(2,25)14-10-12-18-17(19(23)16-20(18)24)11-8-6-5-7-9-15-22/h10,12,17-18,20,22,24-25H,3-9,11,13-16H2,1-2H3/b12-10+/t17-,18-,20-,21?/m1/s1
SMILES Code
CCCCC(C)(O)C/C=C/[C@@H]1[C@H](C(C[C@H]1O)=O)CCCCCCCO
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 354.53 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.

Recalculate based on batch purity %
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: Cohen A, Tolman KG, Lewis GP, Brown S, van Horn A, McCormack GH, Simon DM. The antigastrolesive activity of rioprostil, a 16-methyl prostaglandin-E1 analogue in healthy volunteers. Scand J Gastroenterol Suppl. 1989;164:81-90; discussion 90-1. PubMed PMID: 2510286. 2: Boucekkine T, Meknini B, Bitoun A, Prunièras F, Khedis A, de Lauture D, Rotenberg A, Molinie C, Roux M, Gauthier A, et al. Treatment of duodenal ulcer with rioprostil: a randomized multicentre double-blind study. Scand J Gastroenterol Suppl. 1989;164:191-3. PubMed PMID: 2510266. 3: Fischer S, Schweer H, Kraft H, Weber P. Pharmacokinetics of rioprostil in human plasma as assayed by combined capillary gas chromatography-negative ion chemical ionization mass spectrometry. Scand J Gastroenterol Suppl. 1989;164:59-61; discussion 61-2. PubMed PMID: 2510282. 4: Corsing C, Demol P. Drug safety of rioprostil in patients with active gastric or duodenal ulcer. Scand J Gastroenterol Suppl. 1989;164:232-7; discussion 237-8. PubMed PMID: 2510274. 5: Demol P, Singer MV, Dammann HG, Richardson CT, Weihrauch TR. Effects of rioprostil on gastric acid and pepsin secretion in man: a review of studies in healthy volunteers. Scand J Gastroenterol Suppl. 1989;164:74-9; discussion 79-80. PubMed PMID: 2510285. 6: Bianchi Porro G, Parente F, Hentschel E, Bennani A, Sebti F, Cherkaoui A, Demyttenaere M, Gouerou H, Blasi A, Darnis F, et al. Rioprostil in the short-term treatment of duodenal ulcer: a multicentre double-blind trial vs. cimetidine. Scand J Gastroenterol Suppl. 1989;164:219-23. PubMed PMID: 2510272. 7: Paladini G, Fabiani MG, Tosato F, Maggiolo F. Prophylactic and therapeutic role of rioprostil in NSAIDs induced gastroduodenal lesions. Scand J Gastroenterol Suppl. 1989;164:242-5; discussion 245-6. PubMed PMID: 2510276. 8: Demol P, Wingender W, Weihrauch TR, Graefe KH. Inhibition of gastric secretion in man by rioprostil, a new synthetic methyl prostaglandin E1. Arzneimittelforschung. 1985;35(5):861-3. PubMed PMID: 3927929. 9: Vantrappen G, Janssens J. Effect of rioprostil, 600 micrograms, on the interdigestive myoelectrical activity of the humans small intestine. Scand J Gastroenterol Suppl. 1989;164:133-8; discussion 138-9. PubMed PMID: 2510257. 10: Businger JA, Fumagalli I, Michel H, Delas N, Stocker H. Rioprostil, a new prostaglandin E1 analogue, in the once-daily treatment for the prevention of duodenal ulcer recurrence: a comparison with ranitidine. Scand J Gastroenterol Suppl. 1989;164:152-9; discussion 159-60. PubMed PMID: 2510260. 11: Ahr HJ, Karl W, Scherling D, Wünsche C. Metabolic fate of rioprostil in the rat--in vivo and in liver perfusion. Scand J Gastroenterol Suppl. 1989;164:52-7. PubMed PMID: 2510281. 12: Simon B, Dammann HG, Müller P. Prostaglandins and peptic ulcer disease: nocturnal administration of rioprostil vs ranitidine in duodenal ulcer healing. Klin Wochenschr. 1986;64 Suppl 7:44-6. PubMed PMID: 3104657. 13: Coremans G, Vantrappen G, Businger JA, Demol P. Efficacy and safety of rioprostil, 300 micrograms b.d., in the treatment of duodenal ulcer: a double-blind, controlled multicentre clinical study vs. ranitidine. Scand J Gastroenterol Suppl. 1989;164:198-205; discussion 205-6. PubMed PMID: 2510268. 14: Schulte K, Singer MV, Eysselein V, Demol P, Goebell H. Effect of rioprostil, a synthetic prostaglandin E1 on meal-stimulated gastric acid secretion and plasma gastrin levels in humans. Digestion. 1987;36(3):162-7. PubMed PMID: 3109990. 15: Baunack AR, Demol P, Froese G, Kuhlmann J, Weihrauch TR. Effect of rioprostil, an oral prostaglandin E1 analogue, on lower oesophageal sphincter pressure and on the motility of the distal oesophagus in healthy volunteers. Scand J Gastroenterol Suppl. 1989;164:120-5; discussion 125-6. PubMed PMID: 2510255. 16: Segers O, Somers G. Effect of rioprostil, a methylprostaglandin E1 analog, on basal and stimulated plasma pancreatic hormone levels in man. Dig Dis Sci. 1990 Jan;35(1):20-6. PubMed PMID: 2104796. 17: Katz LB, Genna T, Greeley GH Jr, Shriver DA. Antisecretory and antigastrin effects of rioprostil in gastric fistula dogs. Dig Dis Sci. 1987 Nov;32(11):1268-74. Review. PubMed PMID: 3117511. 18: Penston JG, Johnston DA, Wormsley KG. The effects of rioprostil on gastric emptying and intragastric acidity. Hepatogastroenterology. 1986 Jun;33(3):120-2. PubMed PMID: 3091468. 19: Dammann HG, Dreyer M, Müller P, Simon B. Rioprostil in the acute and long-term treatment of peptic ulcers: a review. Scand J Gastroenterol Suppl. 1989;164:207-11; discussion 212-3. Review. PubMed PMID: 2510269. 20: Shriver DA, Katz LB, Rosenthale ME. Gastric antisecretory and antigastrolesive pharmacology of rioprostil. Scand J Gastroenterol Suppl. 1989;164:10-20. Review. PubMed PMID: 2510252.

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