Lubiprostone

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Cat Number

API136790766

CAS Number

136790-76-6

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Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

136790-76-6

EINECS

603-977-7

Storage

Store at 2-8°C

Synonyms

Lubiprostone hemiketal; SPI-0211; lubiprostona; 7662KG2R6K

Molecular Formula

C20H32F2O5

Molecular Weight

390.5

Smiles

CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)O)(F)F

Appearance

White to light yellow powder to crystal

Melting Point

56-59°C

Boiling Point

539.1±50.0°C (Predicted)

Relative Density

1.143±0.06 (Predicted)

General Description

Lubiprostone is a bicyclic fatty acid derivative of prostaglandin E1, specifically a prostaglandin E1 analog with a 8‑methylene‑17‑oxide structure. The molecule contains a 13,14‑double bond and a 15‑hydroxy group, but the 15‑hydroxy is configured as the R epimer, which differs from naturally occurring PGE1. This structural modification confers selectivity for the type‑2 chloride channel (ClC‑2).

Mechanism of Action

Lubiprostone activates ClC‑2 chloride channels on the apical membrane of intestinal epithelial cells, increasing chloride efflux into the lumen. The resultant increase in luminal chloride draws sodium and water passively via paracellular pathways, softening the stool and increasing intestinal motility. Unlike traditional laxatives, it does not directly affect smooth muscle contractility. The drug also activates prostaglandin EP4 receptors, which may contribute to pro‑motility effects.

Application

Lubiprostone is indicated for chronic idiopathic constipation (CIC), irritable bowel syndrome with constipation (IBS‑C), and opioid‑induced constipation (OIC) in patients with chronic non‑cancer pain.

In mice, lubiprostone stimulated a chloride secretory current that was independent of CFTR (minimally affected by CFTRinh172) and dependent on basolateral bumetanide and barium. In the colon, lubiprostone reduced the thickness of the inner mucus layer in both proximal and distal segments. It also altered the gut microbiome, increasing the abundance of Lactobacillus and Alistipes. The authors conclude that lubiprostone activates non‑CFTR chloride secretion and modifies both colonic mucus and the enteric microbiome.

Fig. 1 Bacterial population analysis for +/ΔF and ΔF/ΔF mice using 16S rRNA clone libraries. (Musch MW, et al., 2013)

References

Musch MW, et al. Lubiprostone decreases mouse colonic inner mucus layer thickness and alters intestinal microbiota. Dig Dis Sci. 2013;58(3):668-677.

In a 48‑week randomized placebo‑controlled trial (116 patients with metabolic dysfunction‑associated steatotic liver disease), lubiprostone 24 µg twice daily significantly reduced liver fat content measured by MRI‑PDFF (P=0.04) compared with placebo, despite greater weight loss in the placebo group. Fibrosis score and ALT levels did not differ. One patient discontinued due to severe diarrhea. Lubiprostone was well tolerated and appears promising for reducing liver fat in MASLD, warranting larger studies.

Fig. 2 Flow chart of patient recruitment and study procedure. (El-Kassas M, et al., 2025)

References

El-Kassas M, et al. Lubiprostone Reduces Fat Content on MRI-PDFF in Patients With MASLD: A 48-Week Randomised Controlled Trial. Aliment Pharmacol Ther. 2025;61(4):628-635.

Does Lubiprostone require refrigerated storage as a prostaglandin analog?

Yes, it must be stored at 2-8°C. The compound is thermally labile; at room temperature, it degrades via isomerization and hydrolysis of the lactone ring.

Is Lubiprostone sensitive to light and moisture during storage?

Yes, it is both photosensitive and hygroscopic. Store in original, tightly sealed, light-resistant containers with desiccant under refrigeration.

What is the stability of Lubiprostone in soft gelatin capsule formulations?

Capsules are stable when packaged in moisture-protective blisters and stored under refrigeration.

How is the impurity lubiprostone free acid (hydrolysis product) monitored?

This primary degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.