Lubiprostone
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MedKoo CAT#: 319935

CAS#: 333963-40-9 (hemiketal)

Description: Lubiprostone, also known as RU-0211, is a medication used in the management of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. It was initially approved by the U.S. Food and Drug Administration (FDA) in 2006. Lubiprostone is a bicyclic fatty acid derived from prostaglandin E1 that acts by specifically activating ClC-2 chloride channels on the apical aspect of gastrointestinal epithelial cells, producing a chloride-rich fluid secretion. These secretions soften the stool, increase motility, and promote spontaneous bowel movements (SBM).

Chemical Structure

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Lubiprostone
CAS# 333963-40-9 (hemiketal)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319935
Name: Lubiprostone
CAS#: 333963-40-9 (hemiketal)
Chemical Formula: C20H32F2O5
Exact Mass: 390.22
Molecular Weight: 390.468
Elemental Analysis: C, 61.52; H, 8.26; F, 9.73; O, 20.49

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1650 Ready to ship
1g USD 2650 Ready to ship
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Related CAS #: 136790-76-6 (open ring)   333963-40-9 (hemiketal),  

Synonym: RU-0211; RU 0211; RU0211; Spi 0211; Spi-0211; Spi0211; Lubiprostone hemiketal; Lubiprostone. trade name Amitiza.

IUPAC/Chemical Name: 7-[(1R,3R,6R,7R)-3-(1,1-Difluoropentyl)-3-hydroxy-8-oxo-2-oxabicyclo[4.3.0]non-7-yl]heptanoic acid

InChi Key: WGFOBBZOWHGYQH-MXHNKVEKSA-N

InChi Code: InChI=1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15-,17-,20-/m1/s1

SMILES Code: O=C(O)CCCCCC[C@@H]1[C@@]2([H])CC[C@](O)(C(F)(F)CCCC)O[C@]2([H])CC1=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, not in water

Shelf Life: >2 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:

Biological target: N/A
In vitro activity: 1. Nishii N, Oshima T, Li M, Eda H, Nakamura K, Tamura A, Ogawa T, Yamasaki T, Kondo T, Kono T, Tozawa K, Tomita T, Fukui H, Miwa H. Lubiprostone Induces Claudin-1 and Protects Intestinal Barrier Function. Pharmacology. 2020;105(1-2):102-108. doi: 10.1159/000503054. Epub 2019 Sep 19. PMID: 31536982.
In vivo activity: To assess this question, lubiprostone was applied to both the mucosal (10 µM) and adventitial (10 µM) side of the porcine esophagus before application of acid. Placement of lubiprostone on control tissues had no significant effect on TER over the course of the experiment (data not shown), whereas pretreatment of both the adventitial and mucosal sides of the tissue with lubiprostone was associated with attenuation of the drop in TER observed after 90 min of acid exposure (Fig. 3A). Furthermore, 90 min after acid was flushed from the bathing reservoir, there was evidence of a recovery response in lubiprostone-pretreated tissues as demonstrated by increased TER in lubiprostone-pretreated tissues versus control (Fig. 3A, n = 5, P < 0.05). Reference: Am J Physiol Gastrointest Liver Physiol. 2020 Apr 1; 318(4): G613–G623. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7191458/

Preparing Stock Solutions

The following data is based on the product molecular weight 390.47 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
Formulation protocol: 1. Nishii N, Oshima T, Li M, Eda H, Nakamura K, Tamura A, Ogawa T, Yamasaki T, Kondo T, Kono T, Tozawa K, Tomita T, Fukui H, Miwa H. Lubiprostone Induces Claudin-1 and Protects Intestinal Barrier Function. Pharmacology. 2020;105(1-2):102-108. doi: 10.1159/000503054. Epub 2019 Sep 19. PMID: 31536982.
In vitro protocol: 1. Nishii N, Oshima T, Li M, Eda H, Nakamura K, Tamura A, Ogawa T, Yamasaki T, Kondo T, Kono T, Tozawa K, Tomita T, Fukui H, Miwa H. Lubiprostone Induces Claudin-1 and Protects Intestinal Barrier Function. Pharmacology. 2020;105(1-2):102-108. doi: 10.1159/000503054. Epub 2019 Sep 19. PMID: 31536982.
In vivo protocol: 1. Akita H, Yoshie S, Ishida T, Takeishi Y, Hazama A. Negative chronotropic and inotropic effects of lubiprostone on iPS cell-derived cardiomyocytes via activation of CFTR. BMC Complement Med Ther. 2020 Apr 19;20(1):118. doi: 10.1186/s12906-020-02923-6. PMID: 32306956; PMCID: PMC7169008. 2. Krüger L, Pridgen TA, Taylor ER, Garman KS, Blikslager AT. Lubiprostone protects esophageal mucosa from acid injury in porcine esophagus. Am J Physiol Gastrointest Liver Physiol. 2020 Apr 1;318(4):G613-G623. doi: 10.1152/ajpgi.00086.2019. Epub 2020 Feb 18. PMID: 32068440; PMCID: PMC7191458.

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1: Spierings EL, Brewer RP, Rauck RL, Losch-Beridon T, Mareya SM. Lubiprostone for Opioid-Induced Constipation Does Not Interfere with Opioid Analgesia in Patients with Chronic Noncancer Pain. Pain Pract. 2016 Mar 15. doi: 10.1111/papr.12444. [Epub ahead of print] PubMed PMID: 26990171.

2: Solem CT, Patel H, Mehta S, Mody R, Macahilig C, Gao X. Treatment patterns, symptom reduction, quality of life, and resource use associated with lubiprostone in irritable bowel syndrome constipation subtype. Curr Med Res Opin. 2016 Mar 11:1-7. [Epub ahead of print] PubMed PMID: 26836030.

3: Spierings EL, Rauck R, Brewer R, Marcuard S, Vallejo R. Long-Term Safety and Efficacy of Lubiprostone in Opioid-induced Constipation in Patients with Chronic Noncancer Pain. Pain Pract. 2015 Aug 29. doi: 10.1111/papr.12347. [Epub ahead of print] PubMed PMID: 26328775.

4: Song J, Yin J, Xu X, Chen J. Prokinetic effects of large-dose lubiprostone on gastrointestinal transit in dogs and its mechanisms. Am J Transl Res. 2015 Mar 15;7(3):513-21. eCollection 2015. PubMed PMID: 26045891; PubMed Central PMCID: PMC4448191.

5: Kang SB, Marchelletta RR, Penrose H, Docherty MJ, McCole DF. A comparison of linaclotide and lubiprostone dosing regimens on ion transport responses in human colonic mucosa. Pharmacol Res Perspect. 2015 Mar;3(2):e00128. doi: 10.1002/prp2.128. Epub 2015 Mar 13. PubMed PMID: 26038704; PubMed Central PMCID: PMC4448989.

6: Jamal MM, Adams AB, Jansen JP, Webster LR. A randomized, placebo-controlled trial of lubiprostone for opioid-induced constipation in chronic noncancer pain. Am J Gastroenterol. 2015 May;110(5):725-32. doi: 10.1038/ajg.2015.106. Epub 2015 Apr 28. PubMed PMID: 25916220; PubMed Central PMCID: PMC4424379.

7: Giannakou A, Dabos KJ, Koulaouzidis A. Lubiprostone in small-bowel capsule endoscopy: meta-analyzing the data. Gastrointest Endosc. 2015 Apr;81(4):1047-8. doi: 10.1016/j.gie.2014.10.001. PubMed PMID: 25805477.

8: Wilson N, Schey R. Lubiprostone in constipation: clinical evidence and place in therapy. Ther Adv Chronic Dis. 2015 Mar;6(2):40-50. doi: 10.1177/2040622314567678. Review. PubMed PMID: 25729555; PubMed Central PMCID: PMC4331234.

9: Kang DW, DiBaise JK, Ilhan ZE, Crowell MD, Rideout JR, Caporaso JG, Rittmann BE, Krajmalnik-Brown R. Gut microbial and short-chain fatty acid profiles in adults with chronic constipation before and after treatment with lubiprostone. Anaerobe. 2015 Jun;33:33-41. doi: 10.1016/j.anaerobe.2015.01.005. Epub 2015 Jan 21. PubMed PMID: 25617726.

10: Matsuura M, Inamori M, Endo H, Matsuura T, Kanoshima K, Inoh Y, Fujita Y, Umezawa S, Fuyuki A, Uchiyama S, Higurashi T, Ohkubo H, Sakai E, Iida H, Nonaka T, Futagami S, Kusakabe A, Maeda S, Nakajima A. Lubiprostone decreases the small bowel transit time by capsule endoscopy: an exploratory, randomised, double-blind, placebo-controlled 3-way crossover study. Gastroenterol Res Pract. 2014;2014:879595. doi: 10.1155/2014/879595. Epub 2014 Dec 29. PubMed PMID: 25614738; PubMed Central PMCID: PMC4295152.

11: Mishima E, Fukuda S, Shima H, Hirayama A, Akiyama Y, Takeuchi Y, Fukuda NN, Suzuki T, Suzuki C, Yuri A, Kikuchi K, Tomioka Y, Ito S, Soga T, Abe T. Alteration of the Intestinal Environment by Lubiprostone Is Associated with Amelioration of Adenine-Induced CKD. J Am Soc Nephrol. 2015 Aug;26(8):1787-94. doi: 10.1681/ASN.2014060530. Epub 2014 Dec 18. PubMed PMID: 25525179; PubMed Central PMCID: PMC4520171.

12: Majewski M, Sarosiek I, Wallner G, Edlavitch SA, Sarosiek J. Stimulation of Mucin, Mucus, and Viscosity during Lubiprostone in Patients with Chronic Constipation may Potentially Lead to Increase of Lubrication. Clin Transl Gastroenterol. 2014 Dec 18;5:e66. doi: 10.1038/ctg.2014.19. PubMed PMID: 25521039; PubMed Central PMCID: PMC4274370.

13: Marciniak CM, Toledo S, Lee J, Jesselson M, Bateman J, Grover B, Tierny J. Lubiprostone vs Senna in postoperative orthopedic surgery patients with opioid-induced constipation: a double-blind, active-comparator trial. World J Gastroenterol. 2014 Nov 21;20(43):16323-33. doi: 10.3748/wjg.v20.i43.16323. PubMed PMID: 25473191; PubMed Central PMCID: PMC4239525.

14: Littlehales EG, Ford AC. Lubiprostone Is Effective in Treating Functional Bowel Disease With Constipation. Clin Gastroenterol Hepatol. 2015 Jul;13(7):1378-9. doi: 10.1016/j.cgh.2014.09.048. Epub 2014 Oct 5. PubMed PMID: 25290533.

15: Jiao HY, Kim DH, Ki JS, Ryu KH, Choi S, Jun JY. Effects of lubiprostone on pacemaker activity of interstitial cells of cajal from the mouse colon. Korean J Physiol Pharmacol. 2014 Aug;18(4):341-6. doi: 10.4196/kjpp.2014.18.4.341. Epub 2014 Aug 13. PubMed PMID: 25177167; PubMed Central PMCID: PMC4146637.

16: Fukudo S, Hongo M, Kaneko H, Takano M, Ueno R. Lubiprostone increases spontaneous bowel movement frequency and quality of life in patients with chronic idiopathic constipation. Clin Gastroenterol Hepatol. 2015 Feb;13(2):294-301.e5. doi: 10.1016/j.cgh.2014.08.026. Epub 2014 Aug 24. PubMed PMID: 25158925.

17: Meyer JM, Cummings MA. Lubiprostone for treatment-resistant constipation associated with clozapine use. Acta Psychiatr Scand. 2014 Jul;130(1):71-2. doi: 10.1111/acps.12259. PubMed PMID: 24912951.

18: Lubiprostone for chronic constipation in adults. Drug Ther Bull. 2014 Apr;52(4):42-4. doi: 10.1136/dtb.2014.4.0246. PubMed PMID: 24722574.

19: Cryer B, Katz S, Vallejo R, Popescu A, Ueno R. A randomized study of lubiprostone for opioid-induced constipation in patients with chronic noncancer pain. Pain Med. 2014 Nov;15(11):1825-34. doi: 10.1111/pme.12437. Epub 2014 Apr 9. PubMed PMID: 24716835; PubMed Central PMCID: PMC4282321.

20: Hayashi S, Kurata N, Yamaguchi A, Amagase K, Takeuchi K. Lubiprostone prevents nonsteroidal anti-inflammatory drug-induced small intestinal damage by suppressing the expression of inflammatory mediators via EP4 receptors. J Pharmacol Exp Ther. 2014 Jun;349(3):470-9. doi: 10.1124/jpet.114.213991. Epub 2014 Apr 8. PubMed PMID: 24713141.