You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-12-07 02:49:43 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
Thumb
Synonyms
ValueSource
AmitizaKegg
RU-0211HMDB
0211, SPIMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Role

Industrial application:

Biological role:

  Modulator:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Multicellular process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogP4.3Not Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-5294000000-b83d3a55a0ca5eba6c03View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06di-9647460000-b581533fe4735515641fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0392000000-baf7c2f7194ed88b0807View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-1893000000-05146ad09171774b81e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vl-9300000000-1a9036825efee41873b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0098000000-cf19376ddba1a5e460daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-1259000000-85786687d62231129447View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7890000000-6c74f2fbdce947cdac53View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01046 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01046 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01046
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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 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 ]