Details of the Drug

General Information of Drug (ID: DMJTEMW)

• Drug Name: Lubiprostone
• Synonyms: Amitiza; Lubiprostone [USAN]; RU 0211; RU0211; SPI 0211; SPI0211; AMITIZA (TN); RU-0211; SPI-0211; Amitiza, RU-0211, SPI-0211, Lubiprostone; (-)-7-((2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta (b)pyran-5-yl)heptanoic acid; (-)-7-((2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta(b)pyran-5-yl)heptanoic acid; 7-((1R,4R,6R,9R)-4-(1,1-difluoropentyl)-4-hydroxy-8-oxo-5-oxabicyclo(4.3.0)non-9-yl)heptanoic acid; 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoic acid

Indication

Disease Entry	ICD 11	Status	REF
Chronic idiopathic constipation	DC32	Approved	[1], [2], [3], [4]

• Therapeutic Class: Anticonstipation Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 390.5
  Topological Polar Surface Area (xlogp); 4
  Rotatable Bond Count (rotbonds); 11
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 7
• ADMET Property: Half-life: The concentration or amount of drug in body reduced by one-half in 0.9 - 1.4 hours [5]
• Chemical Identifiers:
  Formula: C20H32F2O5
  IUPAC Name: 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoic acid
  Canonical SMILES: CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)O)(F)F
  InChI: 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
  InChIKey: WGFOBBZOWHGYQH-MXHNKVEKSA-N
• Cross-matching ID:
  PubChem CID: 157920
  CAS Number: 333963-40-9
  DrugBank ID: DB01046
  TTD ID: D00CTS
  ACDINA ID: D00380

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Chloride channel protein 2 (CLC-2)	TT30NW6	CLCN2_HUMAN	Activator	[6], [7], [8]

Molecular Expression Atlas of This Drug

• The Studied Disease: Chronic idiopathic constipation
• ICD Disease Classification: DC32

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Chloride channel protein 2 (CLC-2)	DTT	CLCN2	8.78E-02	-0.01	-0.06

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Eisenoxyd	E00585	56841934	Colorant
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Lubiprostone 0.024 mg capsule	0.024 mg	Oral Capsule	Oral
Lubiprostone 0.008 mg capsule	0.008 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4242).
• [2] 2006 drug approvals: finding the niche. Nat Rev Drug Discov. 2007 Feb;6(2):99-101.
• [3] Long-term safety and effectiveness of lubiprostone, a chloride channel (ClC-2) activator, in patients with chronic idiopathic constipation. Dig Dis Sci. 2011 Sep;56(9):2639-45.
• [4] Emerging drugs for postoperative ileus. Expert Opin Emerg Drugs. 2007 Nov;12(4):619-26.
• [5] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [6] Lubiprostone stimulates secretion from tracheal submucosal glands of sheep, pigs, and humans. Am J Physiol Lung Cell Mol Physiol. 2009 May;296(5):L811-24.
• [7] Expression of CLCN voltage-gated chloride channel genes in human blood vessels. J Mol Cell Cardiol. 1999 Mar;31(3):657-66.
• [8] Mutations in CLCN2 encoding a voltage-gated chloride channel are associated with idiopathic generalized epilepsies. Nat Genet. 2003 Apr;33(4):527-32.
• [9] Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
• [10] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 699).
• [11] ClC-2 Cl- channels in human lung epithelia: activation by arachidonic acid, amidation, and acid-activated omeprazole. Am J Physiol Cell Physiol. 2001 Jul;281(1):C46-54.