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).


Price and Availability

Size Price Shipping out time Quantity
10mg USD 90 Same day
25mg USD 150 Same day
50mg USD 250 Same day
100mg USD 450 Same day
200mg USD 750 Same day
500mg USD 1650 Same day
1g USD 2650 Same day
5g USD 4950 2 Weeks
20g USD 11650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-31. Prices are subject to change without notice.

Lubiprostone, purity > 98%, is in stock. The Same day shipping after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319935
Name: Lubiprostone
CAS#: 333963-40-9 (hemiketal)
Chemical Formula: C20H32F2O5
Exact Mass: 390.2218
Molecular Weight: 390.4678
Elemental Analysis: C, 61.52; H, 8.26; F, 9.73; O, 20.49


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


Technical Data

Appearance:
Solid powder

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

Certificate of Analysis:

Safety Data Sheet (SDS):

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


References

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.