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Revision as of 12:25, 23 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456658868 of page Lubiprostone for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').  Latest revision as of 06:26, 7 April 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,132 edits add CA 
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{{Short description|Medication used for constipation}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Infobox drug
{{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 420878004
| verifiedrevid = 462094224
| IUPAC_name = 7-non-7-yl]heptanoic acid
| image = Lubiprostone.svg | image = Lubiprostone.svg
| width = 280 | width = 280
| alt =


<!--Clinical data--> <!-- Clinical data -->
| tradename = Amitiza | tradename = Amitiza
| Drugs.com = {{drugs.com|monograph|lubiprostone}} | Drugs.com = {{drugs.com|monograph|lubiprostone}}
| MedlinePlus = a607034 | MedlinePlus = a607034
| licence_US = Lubiprostone | DailyMedID = Lubiprostone
| routes_of_administration = ]
| pregnancy_US = C
| ATC_prefix = A06
| ATC_suffix = AX03

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Health Canada New Drug Authorizations: 2015 Highlights | website=] | date=4 May 2016 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2015-highlights.html | access-date=7 April 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only | legal_US = Rx-only
| legal_US_comment =
| routes_of_administration = ]
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = Negligible | bioavailability = Negligible
| protein_bound = 94% | protein_bound = 94%
| metabolism = Extensive, ] not involved | metabolism = Extensive, ] not involved
| elimination_half-life = Unknown (lubiprostone)<br>0.9–1.4 hours (main metabolite) | elimination_half-life = Unknown (lubiprostone)<br>0.9–1.4 hours (main metabolite)
| excretion = ] (60%) and fecal (30%) | excretion = ] (60%) and fecal (30%)


<!--Identifiers--> <!-- Identifiers -->
| IUPHAR_ligand = 4242
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 136790-76-6 | CAS_number = 136790-76-6
| ATC_prefix = A06
| ATC_suffix = AX03
| PubChem = 157920 | PubChem = 157920
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
Line 34: Line 54:
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 138948 | ChemSpiderID = 138948
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7662KG2R6K | UNII = 7662KG2R6K
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04790 | KEGG = D04790
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201134 --> | ChEMBL = 1201134

| C=20 | H=32 | F=2 | O=5
<!-- Chemical data -->
| molecular_weight = 390.462 g/mol
| IUPAC_name = 7-non-7-yl]heptanoic acid
| C=20 | H=32 | F=2 | O=5
| smiles = FC(F)(CCCC)2(O)O1CC(=O)(1CC2)CCCCCCC(=O)O | smiles = FC(F)(CCCC)2(O)O1CC(=O)(1CC2)CCCCCCC(=O)O
| InChI = 1/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
| InChIKey = WGFOBBZOWHGYQH-MXHNKVEKBM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WGFOBBZOWHGYQH-MXHNKVEKSA-N | StdInChIKey = WGFOBBZOWHGYQH-MXHNKVEKSA-N
| synonyms = Amitiza<br>RU-0211<BR>SPI-0211 | synonyms = RU-0211<BR>SPI-0211
}} }}

'''Lubiprostone''', sold under the brand name '''Amitiza''' among others, is a ] used in the management of ], predominantly ]-associated constipation in women and ]. The drug is owned by ] and is marketed by ].

The drug was developed by ] and approved by the ] (FDA) in 2006.<ref>
{{Cite news | url=https://www.wsj.com/articles/SB113875292044961526 | title=FDA Approves New Type of Drug To Treat Constipation in Adults | work=] | date=February 1, 2006 | url-access=subscription}}</ref><ref name=FDA>{{cite web |title=Highlights of Prescribing Information |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021908s018lbl.pdf |website=FDA |date=2020}}</ref><ref name="Webster2018">{{cite journal | vauthors = Webster LR, Brewer RP, Lichtlen P, Losch-Beridon T, Mareya S, Wang M | title = Efficacy of Lubiprostone for the Treatment of Opioid-Induced Constipation, Analyzed by Opioid Class | journal = Pain Medicine | volume = 19 | issue = 6 | pages = 1195–1205 | date = June 2018 | pmid = 29897589 | doi = 10.1093/pm/pnx212 | doi-access = free }}</ref> It was recommended for use in the UK by the ] (NICE) in July 2014.<ref>{{cite web | url=https://www.nice.org.uk/guidance/ta318/documents/constipation-chronic-idiopathic-lubiprostone-final-appraisal-determination-document2 | title=Final appraisal determination: Lubiprostone for treating chronic idiopathic constipation | publisher=] | date=June 2014}}</ref> ] approved the drug in 2015.<ref>{{cite web | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2015-highlights.html | title=Health Canada New Drug Authorizations: 2015 Highlights | date=2016-05-04 | publisher=]}}</ref> Lubiprostone received approval from the Food and Drug Administration in 2008, to treat irritable bowel syndrome with ] (IBS-C),<ref name=Harvard>{{cite web |title=In the news: FDA approves one drug for irritable bowel syndrome but suspends another |url=https://www.health.harvard.edu/newsletter_article/In_the_news_FDA_approves_one_drug_for_irritable_bowel_syndrome_but_suspends_another |website=Harvard Health |date=2008-08-01}}</ref> and in 2013, for the treatment of opioid-induced constipation in adults with chronic noncancer pain.<ref name="Webster2018"/> It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref>

==Medical uses==
Lubiprostone is a laxative used for the treatment of constipation, specifically:<ref name="MedlinePlus&WebMD">
* {{cite web |title=Lubiprostone: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a607034.html |website=medlineplus.gov |date=2017 |quote=Lubiprostone is also used to treat irritable bowel syndrome with constipation... in women who are at least 18 years of age.}}
* {{cite web |title=Lubiprostone Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing |url=https://www.webmd.com/drugs/2/drug-95017/lubiprostone-oral/details |website=WebMD }}</ref>
* ] (difficult or infrequent passage of stools that lasts for 3 months or longer and is not caused by diet, disease, or drugs).<ref name="MedlinePlus&WebMD"/><ref name=FDA/><ref name=Mayo>{{cite web |title=Lubiprostone (Oral Route) Side Effects |url=https://www.mayoclinic.org/drugs-supplements/lubiprostone-oral-route/side-effects/drg-20069057?p=1 |website=Mayo Clinic |date=2021}}</ref><ref name="Li2016">{{cite journal | vauthors = Li F, Fu T, Tong WD, Liu BH, Li CX, Gao Y, Wu JS, Wang XF, Zhang AP | display-authors = 6 | title = Lubiprostone Is Effective in the Treatment of Chronic Idiopathic Constipation and Irritable Bowel Syndrome: A Systematic Review and Meta-Analysis of Randomized Controlled Trials | journal = Mayo Clinic Proceedings | volume = 91 | issue = 4 | pages = 456–468 | date = April 2016 | pmid = 27046523 | doi = 10.1016/j.mayocp.2016.01.015 | quote = Lubiprostone is a safe and efficacious drug for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation, with limited adverse effects in 3 months of follow-up. }}</ref><ref name=RxList>{{cite web |title=Amitiza (Lubiprostone): Uses, Dosage, Side Effects, Interactions, Warning |url=https://www.rxlist.com/amitiza-drug.htm |website=RxList}}</ref><ref name=Medscape>{{cite web |title=Amitiza (lubiprostone) dosing, indications, interactions, adverse effects, and more |url=https://reference.medscape.com/drug/amitiza-lubiprostone-342076 |website=reference.medscape.com}}</ref><ref name=AHFS>{{cite web | title=Amitiza | url=https://www.drugs.com/monograph/amitiza.html | work=The American Society of Health-System Pharmacists}}</ref>
* Constipation caused by certain opioid (narcotic) pain medications in people with chronic (ongoing), noncancer pain,<ref name="MedlinePlus&WebMD"/> or in patients with long-lasting pain caused by a previous cancer or its treatment who do not need weekly increases in opioid dosage.<ref name="Webster2018"/><ref name=Mayo/><ref name=RxList/><ref name=Medscape/>
** The effectiveness of lubiprostone has not been established in patients who are taking a diphenylheptane opioid (e.g., methadone).<ref name=FDA/><ref name=RxList/>
* ] with constipation (IBS-C; a condition that causes stomach pain or cramps, bloating, and infrequent or difficult passage of stools) in women who are at least 18 years of age.<ref name="MedlinePlus&WebMD"/><ref name=FDA/><ref name=Harvard/><ref name=Mayo/><ref name="Li2016"/><ref name=RxList/><ref name=Medscape/><ref name=AHFS/>

Lubiprostone has not been studied in children.<ref name=Mayo/><ref name=RxList/> There is current research under way to determine the safety and efficacy in postoperative bowel dysfunction.

It comes in a liquid filled capsule and is available only with a doctor's prescription.<ref name=Mayo/> If one misses a dose it should be taken as soon as possible unless it is almost time for the next dose, in which case it should be skipped and the user should return to their regular dosing schedule.<ref name=Mayo/>

==Adverse effects==
In clinical trials, the most common adverse event was ] (31%). Other adverse events (≥5% of patients) included ] (13%), ] (13%), ] (5%), ] (5%), ] (6%), ] (5%), ] (5%), and ] (1%).

The FDA lists the following:<ref name=FDA/>

For subjects with chronic idiopathic constipation taking Amitiza:
* Nausea ~ 29% (4% were severe, and 9% of patients discontinued treatment due to nausea. The rate of nausea was lower among male (8%) and elderly (19%) patients. No patients in the clinical studies were hospitalized due to nausea.)
* Diarrhea: ~12% (2% were severe, and 2% of patients discontinued treatment due to diarrhea)
* Several less common adverse reactions (<1%).

For opioid-induced constipation:
* Nausea: ~ 11%; 1% severe nausea and 2% discontinued treatment due to nausea.
* Diarrhea: ~ 8%; 2% severe diarrhea and 1% of patients discontinued treatment due to diarrhea.
* Less common adverse reactions (<1%): fecal incontinence, blood potassium decreased.

For subjects with irritable bowel syndrome with constipation:
* Nausea: ~ 8%; 1% severe nausea and 1% discontinued treatment due to nausea.
* Diarrhea: ~ 7%; <1% of patients had severe diarrhea and <1% of patients discontinued treatment due to diarrhea.
* Less common adverse reactions: <1%<ref name=FDA/>

A 2018 pooled analysis from three ], randomized, double-blind, placebo-controlled studies on usage for Opioid-Induced Constipation, found that the numbers of patients reporting adverse effects were similar in both the lubiprostone and placebo treatment groups for all opioid classes (P ≥ 0.125); however, gastrointestinal adverse effects were reported more frequently by those receiving lubiprostone than 2 of the 3 opioid groups. The most commonly reported TEAEs in the lubiprostone treatment groups were nausea (13.4%–18.1%), diarrhea (1.2%–13.9%), and abdominal pain (4.7%–5.6%). In the population overall, the greatest likelihood of experiencing the first episode of any of these three TEAEs was greatest in the first week of treatment and decreased thereafter.<ref name="Webster2018"/>

According to Medscape, the most common (>10%) were: Nausea, Diarrhea (7-12%), Headache (2-11%). Less common side effects (1-10%) included: Abdominal pain (4-8%), Abdominal distension (3-6%), Flatulence (4-6%), Vomiting (3%), Loose stools (3%), Edema (1-3%), Abdominal discomfort (1-3%), Dizziness (3%), Chest discomfort/pain (2%), Dyspnea (2%), Dyspepsia (2%), Fatigue (2%), Dry mouth (1%).<ref name=Medscape/>

===Contraindications===

* Known or suspected mechanical GI obstruction.<ref name=FDA/><ref name=AHFS/><ref name=RxList/>
* Known hypersensitivity to lubiprostone or any ingredient in the formulation.<ref name=AHFS/>

The effects on pregnancy have not been studied in humans, but testing in ]s resulted in fetal loss.{{medical citation needed|date=March 2023}}

Lubiprostone is contraindicated in people exhibiting chronic ], ], or diarrhea-predominant ].{{medical citation needed|date=March 2023}}

==Mechanism of action==
{{unreferenced section|date=March 2023}}
Lubiprostone is a bicyclic ]<ref>{{cite journal | vauthors = Lacy BE, Levy LC | title = Lubiprostone: a chloride channel activator | journal = Journal of Clinical Gastroenterology | volume = 41 | issue = 4 | pages = 345–351 | date = April 2007 | pmid = 17413599 | doi = 10.1097/01.mcg.0000225665.68920.df }}</ref> derived from ] that acts by specifically activating ] on the apical aspect of gastrointestinal ] cells, producing a chloride-rich fluid secretion. These secretions soften the stool, increase motility, and promote spontaneous bowel movements.

==Pharmacokinetics==
Unlike many ] products, lubiprostone does not show signs of ], ], or altered serum ] concentration.<ref>{{cite journal | vauthors = Lacy BE, Levy LC | title = Lubiprostone: a novel treatment for chronic constipation | journal = Clinical Interventions in Aging | volume = 3 | issue = 2 | pages = 357–364 | date = June 2008 | pmid = 18686757 | pmc = 2546479 | doi = 10.2147/cia.s2938 | doi-access = free }}</ref>

Minimal distribution of the drug occurs beyond the immediate gastrointestinal tissues.{{medical citation needed|date=March 2023}} Lubiprostone is rapidly metabolized by ]/], mediated by carbonyl reductase.{{medical citation needed|date=March 2023}} There is no metabolic involvement of the hepatic ] system.{{medical citation needed|date=March 2023}} The measurable metabolite, M3, exists in very low levels in plasma and makes up less than 10% of the total administered dose.{{medical citation needed|date=March 2023}}

Data indicate that metabolism occurs locally in the ] and ].{{medical citation needed|date=March 2023}}

== Society and culture ==
=== Economics ===
The cost to the ] was £29.68 per 24&nbsp;mcg 28-cap pack as of April 2017.

=== Brand names ===
Lubiprostone is available in the United States, Japan, Switzerland, India, Bangladesh, the United Kingdom, and Canada.{{citation needed|date=March 2023}}

In ] and ], lubiprostone is sold under the brand name Lubigut by ], Lubilax by ], and under the brand name Lubowel by ].{{citation needed|date=March 2023}}

== References ==
{{Reflist}}

{{Laxatives}}
{{Prostanoidergics}}
{{Portal bar | Medicine}}

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