Structure via PubChem · Public domain (PubChem)
lubiprostone
Sign in to saveAlso known as Amitiza®, SPI-0211, (2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-heptanoic acid
Lubiprostone, sold under the brand name Amitiza among others, is a medication used in the management of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. The drug is owned by Mallinckrodt and is marketed by Takeda Pharmaceutical Company.
Key facts
- Drug.KEGG
- D04790
- Drug.ChEMBL
- 1201134
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462094224
- Drug.image
- Lubiprostone.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 280
- Drug.tradename
- Amitiza
- Drug.MedlinePlus
- a607034
- Drug.DailyMedID
- Lubiprostone
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- A06
- Drug.ATC_suffix
- AX03
- Drug.legal_CA
- Rx-only
- Drug.legal_US
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- Negligible
via Wikipedia infobox
Chemical data
- Formula
- C20H32F2O5
- Molecular weight
- 390.5 g/mol
- 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
- SMILES
- CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)O)(F)F
- InChIKey
- WGFOBBZOWHGYQH-MXHNKVEKSA-N
- XLogP
- 4
- Polar surface area
- 83.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2006
- Admin. routes
- oral
- Indications
- irritable bowel syndrome, Constipation, HIV infection, Chronic pain
via ChEMBL · EBI
Research
481 papers- Lubiprostone.2006
- Lubiprostone.2012
- Comparative profiles of lubiprostone, linaclotide, and elobixibat for chronic constipation: a systematic literature review with meta-analysis and number needed to treat/harm.BMC gastroenterology · 2024
- Lubiprostone in chronic kidney disease: Insights into mitochondrial function and polyamines from a randomized phase 2 clinical trial.Science advances · 2025
- Lubiprostone.Drugs · 2006
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 390.222
- Has use
- medication
Show 6 more facts
- medical condition treated
- constipation
- chemical formula
- C₂₀H₃₂F₂O₅
- canonical SMILES
- CCCCC(C1(CCC2C(O1)CC(=O)C2CCCCCCC(=O)O)O)(F)F
- isomeric SMILES
- CCCCC(F)(F)[C@@]1(O)CC[C@H]2[C@@H](CC(=O)[C@@H]2CCCCCCC(O)=O)O1
- NCI Thesaurus ID
- C66040
- Commons category
- Lubiprostone
Sources (6)
via Wikidata · CC0
~5 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Adverse effects
- Contraindications
- Mechanism of action
- Pharmacokinetics
- Society and culture
- Economics
- Brand names
- References
Lubiprostone, sold under the brand name Amitiza among others, is a medication used in the management of chronic idiopathic constipation, predominantly irritable bowel syndrome-associated constipation in women and opioid-induced constipation. The drug is owned by Mallinckrodt and is marketed by Takeda Pharmaceutical Company.
The drug was developed by Sucampo Pharmaceuticals and approved by the Food and Drug Administration (FDA) in 2006. It was recommended for use in the UK by the National Institute for Health and Care Excellence (NICE) in July 2014. Health Canada approved the drug in 2015. Lubiprostone received approval from the Food and Drug Administration in 2008, to treat irritable bowel syndrome with constipation (IBS-C), and in 2013, for the treatment of opioid-induced constipation in adults with chronic noncancer pain. It is available as a generic medication.
Excerpted from Wikipedia’s “lubiprostone” article, available under the CC BY-SA 4.0 licence.