U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32F2O5
Molecular Weight 390.4619
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUBIPROSTONE

SMILES

[H][C@@]12CC(=O)[C@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC

InChI

InChIKey=WGFOBBZOWHGYQH-MXHNKVEKSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/021908Orig1s008.pdf

Lubiprostone is a medication used in the management of idiopathic chronic constipation. It is a bicyclic fatty acid (prostaglandin E1 derivative) which 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). Lubiprostone acts by specifically activating ClC-2 chloride channels, which is a normal constituent of the apical membrane of the human intestine, in a protein kinase A action independent fashion. Activation of ClC-2 chloride channels causes an efflux of chloride ions into the lumen, which in turn leads to an efflux of sodium ions through a paracellular pathway to maintain isoelectric neutrality. As a result, water follows sodium into the lumen in order to maintain isotonic equilibrium, thereby increasing intestinal fluid secretion. By increasing intestinal fluid secretion, lubiprostone increases motility in the intestine, thereby increasing the passage of stool and alleviating symptoms associated with chronic idiopathic constipation. Activation of ClC-2 chloride channels may also stimulate the recovery of muscosal barrier function by restoring tight junction protein complexes in the intestine. Patch clamp cell studies in human cell lines have indicated that the majority of the beneficial biological activity of lubiprostone and its metabolites is observed only on the apical (luminal) portion of the gastrointestinal epithelium. Lubiprostone is marketed under the trade name Amitiza among others.

Originator

Approval Year

2006
178
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Amitiza

Approved Use

Amitiza is a chloride channel activator indicated for: • Treatment of chronic idiopathic constipation in adults • Treatment of irritable bowel syndrome with constipation in women ≥ 18 years old

Launch Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
41.5 pg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
37.5 pg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
57.1 pg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
39.6 pg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.15 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
24 μg single, oral
dose: 24 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
15-HYDROXY LUBIPROSTONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
24 ug 2 times / day multiple, oral
Recommended
Dose: 24 ug, 2 times / day
Route: oral
Route: multiple
Dose: 24 ug, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
unhealthy
n = 1113
Health Status: unhealthy
Condition: Chronic idiopathic constipation
Population Size: 1113
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
Disc. AE: Nausea, Dyspnea...
AEs leading to
discontinuation/dose reduction:
Nausea (9%)
Dyspnea (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Other AEs: Nausea, Diarrhea...
Other AEs:
Nausea (45%)
Diarrhea (35%)
Vomiting (27%)
Dizziness (14%)
Headache (12%)
Abdominal pain (8%)
Flash hot (8%)
Retching (8%)
Dyspnea (4%)
Pallor (4%)
Stomach discomfort (4%)
Anorexia (2%)
Asthenia (2%)
Chest discomfort (2%)
Dry mouth (2%)
Hyperhidrosis (2%)
Syncope (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
AEs

AEs

AESignificanceDosePopulation
Dyspnea 2%
Disc. AE
24 ug 2 times / day multiple, oral
Recommended
Dose: 24 ug, 2 times / day
Route: oral
Route: multiple
Dose: 24 ug, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
unhealthy
n = 1113
Health Status: unhealthy
Condition: Chronic idiopathic constipation
Population Size: 1113
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
Nausea 9%
Disc. AE
24 ug 2 times / day multiple, oral
Recommended
Dose: 24 ug, 2 times / day
Route: oral
Route: multiple
Dose: 24 ug, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
unhealthy
n = 1113
Health Status: unhealthy
Condition: Chronic idiopathic constipation
Population Size: 1113
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.1, 4
Headache 12%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Dizziness 14%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Anorexia 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Asthenia 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Chest discomfort 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Dry mouth 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Hyperhidrosis 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Syncope 2%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Vomiting 27%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Diarrhea 35%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Dyspnea 4%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Pallor 4%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Stomach discomfort 4%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Nausea 45%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Abdominal pain 8%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Flash hot 8%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Retching 8%
144 ug single, oral
Studied dose
Dose: 144 ug
Route: oral
Route: single
Dose: 144 ug
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
healthy
n = 51
Health Status: healthy
Population Size: 51
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021908s010lbl.pdf
Page: p.8
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

inducer
781
inhibitor
1767

inducer
389
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2C19
1478

CYP2E1
882

CYP
111
CYP
270
CYP1A2
701

CYP2B6
547

CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
739
 likely
CYP
147
 no
CYP
147
 no
CYP1A2
1692
 no
CYP1A2
1692
 no
CYP2A6
739
 no
CYP2B6
1001
 no
CYP2B6
1001
 no
CYP2C19
1553
 no
CYP2C9
1819
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP2E1
970
 no
CYP3A4
1925
 no
CYP3A4
1925
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
AK Scientific, Inc. (AKSCI)
N917
http://www.aksci.com/item_detail.php?cat=N917
AK Scientific, Inc. (AKSCI)
X6870
http://www.aksci.com/item_detail.php?cat=X6870
AK Scientific, Inc. (AKSCI)
Z6115
http://www.aksci.com/item_detail.php?cat=Z6115
AbMole Bioscience
M3459
http://www.abmole.com/products/lubiprostone.html
Alfa Chemistry
AP136790766
https://reagents.alfa-chemistry.com/product/lubiprostone-cas-136790-76-6-4303.html
Alichem
119001436
http://www.alichem.com/en/products/333963-40-9.html
Allbio Pharm Co., Ltd
AF09449
http://www.allbiopharm.com/product/n/AF09449
Ambinter
Amb17772254
http://www.ambinter.com/reference/17772254
Angene
AGN-PC-0R8X2U
http://www.angenechemical.com/productshow/AGN-PC-0R8X2U.html
ApexBio Technology
B2108
http://www.apexbt.com/lubiprostone.html
AvaChem Scientific
2629
http://www.avachem.com/productSearch.asp?2629
BLD Pharm
BD449029
http://www.bldpharm.com/products/333963-40-9.html
BioSynth
J-006909
https://www.biosynth.com/en/products/all-products/products/J-006909.html
Boerchem
BC677681
http://www.boerchem.com/?product_39566.html
ChemFish Tokyo co.,ltd
157920
http://www.chemfish.co.jp/index.php?id=2925&project=product
ChemMol
30108352
http://www.chemmol.com/chemmol/30108352.html
ChemMol
44009988
http://www.chemmol.com/chemmol/44009988.html
ChemMol
49401148
http://www.chemmol.com/chemmol/49401148.html
Chemspace
CSSB00020619493
https://chem-space.com/CSSB00020619493
DC Chemicals
DC8287
http://www.dcchemicals.com/product_show-Lubiprostone.html
Excenen
EX-A1771
http://www.excenen.com/searchresultlist.php?id=333963-40-9
Fluoropharm
YF10093
http://www.fluoropharm.com/product/YF10093.html
Hairui
HR124861
http://www.hairuichem.com/en/product/136790-76-6.html
Hairui
HR34159
http://www.hairuichem.com/en/product/333963-40-9.html
MuseChem
I007731
https://www.musechem.com/product/I007731.html
OChem
26475
http://www.ocheminc.com/index.php?act=psearch&pid=963L409
Renno Tech
RP17713
http://www.rennotech.com/product_show.asp?id=23591
Renno Tech
RL03218
http://www.rennotech.com/product_show.asp?id=3467
Smolecule
S533727
http://www.smolecule.com/products/s533727
THE BioTek
bt-274371
https://www.thebiotek.com/product/inhibitors/bt-274371
THE BioTek
bt-315004
https://www.thebiotek.com/product/others/bt-315004
THE BioTek
bt-461346
https://www.thebiotek.com/product/others/bt-461346
Tenova Pharmaceuticals Inc
T31084
https://www.tenovapharma.com/Lubiprostone
Yuhao Chemical
LX2755
http://www.chemyuhao.com/136790-76-6.html
abcr GmbH
AB456001
http://www.abcr.com/shop/en/AB456001
eNovation Chemicals
D371587
http://www.enovationchem.com/productDetails.asp?productID=D371587
eNovation Chemicals
D630727
https://www.enovationchem.com/ProductDetails.asp?ProductID=D630727
eNovation Chemicals
Y0974121
https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974121
eNovation Chemicals
Y1082345
https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1082345
iChemical
EBD2197415
http://www.ichemical.com/products/136790-76-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
iChemical
EBD3052237
http://www.ichemical.com/products/333963-40-9.html
PubMed

PubMed

TitleDatePubMed
FDA approves one drug for irritable bowel syndrome but suspends another.
2008 Aug
Lubiprostone for chronic idiopathic constipation and irritable bowel syndrome with constipation.
2008 Aug
Lubiprostone for constipation and irritable bowel syndrome with constipation.
2008 Dec
Opioid-induced bowel dysfunction.
2008 Feb
Conquering IBS in women: the clinician's pursuit of optimum management strategies.
2008 Jul
Pharmaceutical approval update.
2008 Jun
Lubiprostone activates non-CFTR-dependent respiratory epithelial chloride secretion in cystic fibrosis mice.
2008 Nov
[Functional and motor gastrointestinal disorders].
2008 Oct
Comparison of the chloride channel activator lubiprostone and the oral laxative Polyethylene Glycol 3350 on mucosal barrier repair in ischemic-injured porcine intestine.
2008 Oct 21
Cellular mechanisms underlying the laxative effect of flavonol naringenin on rat constipation model.
2008 Oct 3
Lubiprostone--a novel treatment for irritable bowel syndrome with constipation.
2008 Sep
Gateways to clinical trials.
2008 Sep
Constipation in the elderly: management strategies.
2009
Function and dysfunction of the colon and anorectum in adults: working team report of the Swedish Motility Group (SMoG).
2009
Stimulation of mucosal secretion by lubiprostone (SPI-0211) in guinea pig small intestine and colon.
2009 Apr
Treatment of dysautonomia associated with Parkinson's disease.
2009 Dec
The FDA and IBS drug development.
2009 Dec
Effect of a chloride channel activator, lubiprostone, on colonic sensory and motor functions in healthy subjects.
2009 Feb
Clinical trial: lubiprostone in patients with constipation-associated irritable bowel syndrome--results of two randomized, placebo-controlled studies.
2009 Feb 1
Lubiprostone: chronic constipation and irritable bowel syndrome with constipation.
2009 Jan
Constipation: evaluation and treatment of colonic and anorectal motility disorders.
2009 Jan
Pathogenesis and management of irritable bowel syndrome.
2009 Jan-Mar
A 73-year-old man with long-term immobility presenting with abdominal pain.
2009 Jul 14
To the editor. CLC chloride channels and transporters: from genes to protein structure, pathology and physiology.
2009 Jun
To the editor. CLC chloride channels and transporters: from genes to protein structure, pathology and physiology.
2009 Jun
Green light from the FDA for new drug development in irritable bowel syndrome and functional dyspepsia.
2009 Jun
Lubiprostone: in constipation-predominant irritable bowel syndrome.
2009 Jun 18
Lubiprostone to prevent fecal impaction.
2009 Mar
Lubiprostone: clinical applications beyond constipation.
2009 Mar 7
Treatment approaches to irritable bowel syndrome.
2009 May
The use of novel promotility and prosecretory agents for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation.
2009 May
Lubiprostone: trials and tribulations.
2009 May
Lubiprostone stimulates secretion from tracheal submucosal glands of sheep, pigs, and humans.
2009 May
Lubiprostone neither decreases gastric and small-bowel transit time nor improves visualization of small bowel for capsule endoscopy: a double-blind, placebo-controlled study.
2009 Nov
Lubiprostone stimulates duodenal bicarbonate secretion in rats.
2009 Oct
Management of irritable bowel syndrome.
2009 Sep
Activation of intestinal Cl- secretion by lubiprostone requires the cystic fibrosis transmembrane conductance regulator.
2009 Sep
Efficacy and safety of lubiprostone in patients with chronic constipation.
2010 Apr
Update on the management of constipation in the elderly: new treatment options.
2010 Aug 9
Dynamic [Cl(-)](i) measurement with chloride sensing quantum dots nanosensor in epithelial cells.
2010 Feb 5
Review article: new receptor targets for medical therapy in irritable bowel syndrome.
2010 Jan
Prostaglandin E2-induced colonic secretion in patients with and without colorectal neoplasia.
2010 Jan 26
[New drugs for the treatment of constipation].
2010 Jul
Lubiprostone reverses the inhibitory action of morphine on intestinal secretion in guinea pig and mouse.
2010 Jul
Emerging new therapeutic options for the management of opioid induced constipation.
2010 Mar
Use of the chloride channel activator lubiprostone for constipation in adults with cystic fibrosis: a case series.
2010 Mar
Enteric nervous system: sensory physiology, diarrhea and constipation.
2010 Mar
Emerging pharmacologic therapies for irritable bowel syndrome.
2010 Oct
Pharmacologic management of chronic constipation.
2010 Sep
Lubiprostone ameliorates the cystic fibrosis mouse intestinal phenotype.
2010 Sep 15
Patents

Patents

20050148573
2
20050277673
1
20060122411
1
20060194842
1
20060240106
2

Sample Use Guides

In Vivo Use Guide
Chronic idiopathic constipation • 24 mcg taken twice daily orally with food and water Irritable bowel syndrome with constipation • 8 mcg taken twice daily orally with food and water
Route of Administration: Oral
In Vitro Use Guide
Lubiprostone, applied to the small intestinal mucosa in eight concentrations ranging from 1-3000 nM, evokes increases in Isc in a concentration-dependent manner with an EC50 of 42.5 nM. Lubiprostone applied to the mucosa of the colon in eight concentrations ranging from 1-3000 nM evokes increases in Isc in a concentration-dependent manner with an EC50 of 31.7 nM
Name Type Language
LUBIPROSTONE
INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
AMITIZA
Brand Name English
LUBIPROSTONE [JAN]
Common Name English
RU-0211
Code English
lubiprostone [INN]
Common Name English
Lubiprostone [WHO-DD]
Common Name English
7-[(2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl]heptanoic acid
Systematic Name English
LUBIPROSTONE [USAN]
Common Name English
(-)-7-((2R,4AR,5R,7AR)-2-(1,1-DIFLUOROPENTYL)-2-HYDROXY-6-OXOOCTAHYDROCYCLOPENTA(B)PYRAN-5-YL)HEPTANOIC ACID
Common Name English
LUBIPROSTONE [VANDF]
Common Name English
LUBIPROSTONE [ORANGE BOOK]
Common Name English
LUBIPROSTONE [MI]
Common Name English
PROSTAN-1-OIC ACID, 16,16-DIFLUORO-11-HYDROXY-9,15-DIOXO-, (11.ALPHA.)-
Common Name English
LUBIPROSTONE [MART.]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175456
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
WHO-VATC QA06AX03
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
WHO-ATC A06AX03
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
LIVERTOX NBK548000
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
NCI_THESAURUS C78568
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
NDF-RT N0000175573
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
Code System Code Type Description
SMS_ID
100000124449
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201134
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
PUBCHEM
157920
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
PRIMARY
MERCK INDEX
m6919
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY Merck Index
DAILYMED
7662KG2R6K
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
INN
8254
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
RXCUI
623033
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
Lubiprostone
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
PRIMARY
DRUG CENTRAL
4123
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
DRUG BANK
DB01046
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
MESH
C506401
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
IUPHAR
4242
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
CAS
333963-40-9
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
ALTERNATIVE
FDA UNII
7662KG2R6K
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
EVMPD
SUB32077
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID5048639
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
USAN
NN-66
Created by admin on Sat Dec 16 16:45:43 GMT 2023 , Edited by admin on Sat Dec 16 16:45:43 GMT 2023
PRIMARY
NCI_THESAURUS
C66040
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
LACTMED
Lubiprostone
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
CAS
136790-76-6
Created by admin on Sat Dec 16 16:45:42 GMT 2023 , Edited by admin on Sat Dec 16 16:45:42 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of LUBIPROSTONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966