Lubiprostone (CED0006949)

Record Information

Version

1.0

Creation Date

2016-05-22 06:36:06 UTC

Update Date

2026-08-20 06:44:20 UTC

Accession Number

CHEM019877

Identification

Common Name

Lubiprostone

Class

Small Molecule

Description

Lubiprostone is an organic compound with the formula C20H32F2O5 and an average molecular weight of 390.47 g/mol. Lubiprostone belongs to the eicosanoids, a subclass of fatty acyls within the organic compounds. It is identified as an inducer of the chloride channel protein 2 (CLCN2). The compound is found in or released from three recorded sources, including healthcare, pharmaceuticals, and veterinary products as drugs for constipation, as well as household cleaning and consumer products such as other smoking requisites and non-electric simulated smoking devices. The recorded exposure route for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amitiza	ChEMBL
7-[(2R,4Ar,5R,7ar)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoate	Generator
0211, SPI	MeSH
Lubiprostone	MeSH
7-[(2R,4AR,5R,7ar)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoate	Generator

Chemical Formula

C₂₀H₃₂F₂O₅

Average Molecular Mass

390.468 g/mol

Monoisotopic Mass

390.222 g/mol

CAS Registry Number

136790-76-6

IUPAC Name

7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

Traditional Name

lubiprostone

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-/m1/s1

InChI Key

WGFOBBZOWHGYQH-MXHNKVEKSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.76	ALOGPS
logP	4.56	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	95.6 m³·mol⁻¹	ChemAxon
Polarizability	42.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abl-0391000000-d507188612a9740a0398	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1973000000-9b4734d4f0a783855588	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gbc-9400000000-04f707ff6d3872eb918f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1097000000-acfe0f9f285ae1ebd734	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000j-2269000000-19bb2b32b6aefcbe4cd4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-7980000000-0fd8f9a14b6b0de95a9f	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
530.0	Log mg/kg	[300:940]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
253	Drugs for constipation	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Lubiprostone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Nuclear receptor subfamily 4 group A member 2	Q06219	Mus musculus	Predicted (SEA)	0.856341
Click to view 3D structure	Nuclear receptor subfamily 4 group A member 2	Q07917	Rattus norvegicus	Predicted (SEA)	0.544945
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Predicted (SEA)	8.87481
Click to view 3D structure	Prostacyclin receptor	P43119	Humans	Predicted (SEA)	5.91654
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P43115	Humans	Predicted (SEA)	17.5939
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P34995	Humans	Predicted (SEA)	17.049
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P35408	Humans	Predicted (SEA)	24.4447
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P35375	Mus musculus	Predicted (SEA)	9.57545
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P30557	Mus musculus	Predicted (SEA)	11.5217
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P32240	Mus musculus	Predicted (SEA)	10.821
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	Q62053	Mus musculus	Predicted (SEA)	9.18621
Click to view 3D structure	Solute carrier organic anion transporter family member 2B1	Q9JHI3	Rattus norvegicus	Predicted (SEA)	1.47914
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	96.9223
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	126.116
Click to view 3D structure	Peroxisome proliferator-activated receptor delta	Q03181	Humans	Predicted (SEA)	107.043
Click to view 3D structure	Thromboxane A2 receptor	P21731	Humans	Predicted (SEA)	57.7641
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	288.198
Click to view 3D structure	Transcriptional activator protein LasR	P25084	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)	Predicted (SEA)	6.30579
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 2	Q9WUD2	Rattus norvegicus	Predicted (SEA)	31.0618
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P43114	Rattus norvegicus	Predicted (SEA)	8.56341
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	Q62928	Rattus norvegicus	Predicted (SEA)	6.15009
Click to view 3D structure	Histone deacetylase 11	Q96DB2	Humans	Predicted (SEA)	616.332
Click to view 3D structure	Prostaglandin D2 receptor	Q13258	Humans	Predicted (SEA)	230.044
Click to view 3D structure	G-protein coupled receptor 84	Q9NQS5	Humans	Predicted (SEA)	22.8098
Click to view 3D structure	Fatty-acid amide hydrolase 1	O00519	Humans	Predicted (SEA)	775.378