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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015180
Secondary Accession Numbers
  • HMDB15180
Metabolite Identification
Common NameLubiprostone
DescriptionLubiprostone 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).
Structure
Data?1582753267
Synonyms
ValueSource
AmitizaKegg
RU-0211HMDB
0211, SPIHMDB
LubiprostoneKEGG
7-[(2R,4AR,5S,7ar)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoateGenerator
Chemical FormulaC20H32F2O5
Average Molecular Weight390.4619
Monoisotopic Molecular Weight390.221780544
IUPAC Name7-[(2R,4aR,5S,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
Traditional Namelubiprostone
CAS Registry Number136790-76-6
SMILES
[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC
InChI Identifier
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+/m0/s1
InChI KeyWGFOBBZOWHGYQH-DKYLXPRQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Medium-chain fatty acid
  • Halogenated fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Oxane
  • Fatty acid
  • Fluorohydrin
  • Halohydrin
  • Hemiacetal
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organohalogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Organic oxygen compound
  • Organofluoride
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogP4.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP2.76ALOGPS
logP4.56ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity95.6 m³·mol⁻¹ChemAxon
Polarizability41.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-227.6630932474
DeepCCS[M+Na]+203.55430932474
AllCCS[M+H]+199.332859911
AllCCS[M+H-H2O]+196.932859911
AllCCS[M+NH4]+201.532859911
AllCCS[M+Na]+202.132859911
AllCCS[M-H]-198.332859911
AllCCS[M+Na-2H]-199.532859911
AllCCS[M+HCOO]-201.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lubiprostone[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC3584.3Standard polar33892256
Lubiprostone[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC2674.3Standard non polar33892256
Lubiprostone[H][C@@]12CC(=O)[C@@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](O)(O2)C(F)(F)CCCC2693.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lubiprostone,1TMS,isomer #1CCCCC(F)(F)[C@@]1(O)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]2O12625.2Semi standard non polar33892256
Lubiprostone,1TMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O)C(=O)C[C@H]2O12672.4Semi standard non polar33892256
Lubiprostone,1TMS,isomer #3CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]2O12681.9Semi standard non polar33892256
Lubiprostone,1TMS,isomer #4CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O)O12615.4Semi standard non polar33892256
Lubiprostone,2TMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C)C(=O)C[C@H]2O12682.4Semi standard non polar33892256
Lubiprostone,2TMS,isomer #2CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O12694.0Semi standard non polar33892256
Lubiprostone,2TMS,isomer #3CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O12679.0Semi standard non polar33892256
Lubiprostone,2TMS,isomer #4CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]2O12743.4Semi standard non polar33892256
Lubiprostone,2TMS,isomer #5CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O)O12679.7Semi standard non polar33892256
Lubiprostone,3TMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O12736.0Semi standard non polar33892256
Lubiprostone,3TMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O12843.1Standard non polar33892256
Lubiprostone,3TMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]2O12874.2Standard polar33892256
Lubiprostone,3TMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O12728.7Semi standard non polar33892256
Lubiprostone,3TMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O12781.2Standard non polar33892256
Lubiprostone,3TMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C)O12897.3Standard polar33892256
Lubiprostone,1TBDMS,isomer #1CCCCC(F)(F)[C@@]1(O)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]2O12863.8Semi standard non polar33892256
Lubiprostone,1TBDMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O)C(=O)C[C@H]2O12897.6Semi standard non polar33892256
Lubiprostone,1TBDMS,isomer #3CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O12896.1Semi standard non polar33892256
Lubiprostone,1TBDMS,isomer #4CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O)O12838.7Semi standard non polar33892256
Lubiprostone,2TBDMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2[C@H](CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C[C@H]2O13163.5Semi standard non polar33892256
Lubiprostone,2TBDMS,isomer #2CCCCC(F)(F)[C@@]1(O)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O13146.3Semi standard non polar33892256
Lubiprostone,2TBDMS,isomer #3CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O13137.0Semi standard non polar33892256
Lubiprostone,2TBDMS,isomer #4CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O13176.5Semi standard non polar33892256
Lubiprostone,2TBDMS,isomer #5CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O)O13137.6Semi standard non polar33892256
Lubiprostone,3TBDMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O13407.7Semi standard non polar33892256
Lubiprostone,3TBDMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O13278.1Standard non polar33892256
Lubiprostone,3TBDMS,isomer #1CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]2O13119.2Standard polar33892256
Lubiprostone,3TBDMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O13398.9Semi standard non polar33892256
Lubiprostone,3TBDMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O13120.6Standard non polar33892256
Lubiprostone,3TBDMS,isomer #2CCCCC(F)(F)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H]2CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O13109.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lubiprostone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-5294000000-b83d3a55a0ca5eba6c032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lubiprostone GC-MS (2 TMS) - 70eV, Positivesplash10-06di-9647460000-b581533fe4735515641f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lubiprostone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lubiprostone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 10V, Positive-QTOFsplash10-05fr-0392000000-baf7c2f7194ed88b08072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 20V, Positive-QTOFsplash10-05fr-1893000000-05146ad09171774b81e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 40V, Positive-QTOFsplash10-07vl-9300000000-1a9036825efee41873b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 10V, Negative-QTOFsplash10-000i-0098000000-cf19376ddba1a5e460da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 20V, Negative-QTOFsplash10-007a-1259000000-85786687d622311294472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 40V, Negative-QTOFsplash10-0a4i-7890000000-6c74f2fbdce947cdac532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 10V, Positive-QTOFsplash10-05fr-0009000000-35b5046ad072d78455ad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 20V, Positive-QTOFsplash10-0avm-2039000000-2b4a8e65036c57034fc42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 40V, Positive-QTOFsplash10-0aor-9520000000-990c2c5e8a719726e6c92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 10V, Negative-QTOFsplash10-000i-0009000000-a5d6e24227bc8251fbe72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 20V, Negative-QTOFsplash10-000i-0029000000-bb4185547119f78da3db2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lubiprostone 40V, Negative-QTOFsplash10-00kr-0193000000-9320001baca5e457ccf22021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01046 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01046 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID571057
KEGG Compound IDC13707
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLubiprostone
METLIN IDNot Available
PubChem Compound656719
PDB IDNot Available
ChEBI ID34945
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
  2. Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]
  3. Crowell MD, Harris LA, DiBaise JK, Olden KW: Activation of type-2 chloride channels: a novel therapeutic target for the treatment of chronic constipation. Curr Opin Investig Drugs. 2007 Jan;8(1):66-70. [PubMed:17263187 ]
  4. Ambizas EM, Ginzburg R: Lubiprostone: a chloride channel activator for treatment of chronic constipation. Ann Pharmacother. 2007 Jun;41(6):957-64. Epub 2007 May 22. [PubMed:17519292 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
References
  1. Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
  2. Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]
General function:
Involved in voltage-gated chloride channel activity
Specific function:
Voltage-gated chloride channel. Chloride channels have several functions including the regulation of cell volume; membrane potential stabilization, signal transduction and transepithelial transport
Gene Name:
CLCN2
Uniprot ID:
P51788
Molecular weight:
98534.4
References
  1. Authors unspecified: Lubiprostone: RU 0211, SPI 0211. Drugs R D. 2005;6(4):245-8. [PubMed:15991886 ]
  2. Moeser AJ, Nighot PK, Engelke KJ, Ueno R, Blikslager AT: Recovery of mucosal barrier function in ischemic porcine ileum and colon is stimulated by a novel agonist of the ClC-2 chloride channel, lubiprostone. Am J Physiol Gastrointest Liver Physiol. 2007 Feb;292(2):G647-56. Epub 2006 Oct 19. [PubMed:17053162 ]
  3. Lacy BE, Levy LC: Lubiprostone: a chloride channel activator. J Clin Gastroenterol. 2007 Apr;41(4):345-51. [PubMed:17413599 ]
  4. Crowell MD, Harris LA, DiBaise JK, Olden KW: Activation of type-2 chloride channels: a novel therapeutic target for the treatment of chronic constipation. Curr Opin Investig Drugs. 2007 Jan;8(1):66-70. [PubMed:17263187 ]
  5. Lacy BE, Chey WD: Lubiprostone: chronic constipation and irritable bowel syndrome with constipation. Expert Opin Pharmacother. 2009 Jan;10(1):143-52. doi: 10.1517/14656560802631319 . [PubMed:19236188 ]
  6. Ambizas EM, Ginzburg R: Lubiprostone: a chloride channel activator for treatment of chronic constipation. Ann Pharmacother. 2007 Jun;41(6):957-64. Epub 2007 May 22. [PubMed:17519292 ]
  7. Lacy BE, Levy LC: Lubiprostone: a novel treatment for chronic constipation. Clin Interv Aging. 2008;3(2):357-64. [PubMed:18686757 ]
  8. Johanson JF, Ueno R: Lubiprostone, a locally acting chloride channel activator, in adult patients with chronic constipation: a double-blind, placebo-controlled, dose-ranging study to evaluate efficacy and safety. Aliment Pharmacol Ther. 2007 Jun 1;25(11):1351-61. [PubMed:17509103 ]
  9. Kapoor S: Emerging new therapeutic options for the management of opioid induced constipation. J Pain Palliat Care Pharmacother. 2010 Mar;24(1):98-9. doi: 10.3109/15360280903475593. [PubMed:20345211 ]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]