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| 1mg |
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| 2mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
15-Hydroxy Lubiprostone acts as a chloride channel opener, specifically targeting the type 2 chloride channel (ClC-2) in the gastrointestinal tract. By opening these channels, the compound increases chloride ion secretion into the intestinal lumen, which promotes fluid secretion and enhances gastrointestinal motility. This mechanism is responsible for the laxative effects of lubiprostone and its metabolites in the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation. The compound is a prostaglandin E analog with biological activity similar to the parent compound.
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| ln Vitro |
15-Hydroxy Lubiprostone is the active metabolite of lubiprostone and retains chloride channel-opening activity. As a prostaglandin E analog, it activates ClC-2 chloride channels in intestinal epithelial cells, leading to increased chloride and fluid secretion. The compound's activity has been characterized in various in vitro models of intestinal epithelial function. Its potency and efficacy in stimulating chloride secretion are comparable to the parent compound. The metabolite contributes to the overall pharmacological effect of lubiprostone therapy.
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| ln Vivo |
As an active metabolite of lubiprostone, 15-hydroxy lubiprostone contributes to the in vivo pharmacological effects of the parent drug. Following oral administration of lubiprostone, the compound is metabolized to 15-hydroxy lubiprostone, which retains chloride channel-opening activity. The metabolite, along with the parent compound, mediates the therapeutic effects on gastrointestinal motility and fluid secretion. In clinical use, lubiprostone is effective for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation.
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| Enzyme Assay |
As a reference standard and metabolite, 15-hydroxy lubiprostone is used in analytical method development and validation rather than in primary pharmacological assays. However, chloride channel activity can be assessed using electrophysiological techniques such as Ussing chamber studies with intestinal epithelial monolayers. The compound's ability to stimulate chloride secretion is measured by monitoring short-circuit current changes. Standard pharmacological assays for prostaglandin E analogs may also be employed.
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| Cell Assay |
Cell-based assays for 15-hydroxy lubiprostone typically employ intestinal epithelial cell lines such as T84 or Caco-2 cells grown on permeable supports to form polarized monolayers. Chloride secretion is measured in Ussing chambers by monitoring short-circuit current (Isc) in response to compound addition. Alternatively, fluorescent chloride-sensitive dyes can be used to measure intracellular chloride levels. The compound's activity is compared with the parent compound lubiprostone. Concentration-response curves are generated to determine potency and efficacy.
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| Animal Protocol |
In vivo activity of 15-hydroxy lubiprostone is evaluated in animal models of gastrointestinal motility and constipation, such as rodent models of loperamide-induced constipation. The compound would be administered orally or intraperitoneally, and gastrointestinal transit time, fecal output, and intestinal fluid content would be measured. However, as 15-hydroxy lubiprostone is a metabolite rather than a primary therapeutic agent, most in vivo data are derived from studies with the parent compound lubiprostone.
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| ADME/Pharmacokinetics |
15-Hydroxy Lubiprostone has molecular formula C20H34F2O5 and molecular weight 392.48. It is the 15-hydroxy metabolite of lubiprostone, formed by metabolic reduction of the 15-keto group. As an active metabolite, it contributes to the overall pharmacokinetic and pharmacodynamic profile of lubiprostone. The compound is used as a reference standard for analytical method development, method validation, and quality control applications in pharmaceutical manufacturing.
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| Toxicity/Toxicokinetics |
Toxicological data for 15-hydroxy lubiprostone are generally derived from studies of the parent compound lubiprostone. As a prostaglandin E analog, potential adverse effects may include nausea, diarrhea, abdominal pain, and headache. The compound should be handled with appropriate laboratory safety precautions. As an active pharmaceutical ingredient metabolite, its safety profile is well-characterized through the clinical development of lubiprostone.
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| Additional Infomation |
15-Hydroxy Lubiprostone is an active metabolite of lubiprostone, a FDA-approved drug for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation. The compound is used as a reference standard for analytical method development and quality control in pharmaceutical manufacturing. It is a halogenated bioactive lipid and prostaglandin E analog with chloride channel-opening activity.
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| Molecular Formula |
C20H34F2O5
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|---|---|
| Molecular Weight |
392.477774143219
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| Exact Mass |
392.237
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| CAS # |
475992-30-4
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| PubChem CID |
9800692
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
559.8±50.0 °C at 760 mmHg
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| Flash Point |
292.4±30.1 °C
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| Vapour Pressure |
0.0±3.5 mmHg at 25°C
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| Index of Refraction |
1.483
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| LogP |
1.87
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
27
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| Complexity |
469
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| Defined Atom Stereocenter Count |
4
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| SMILES |
CCCCC(C(CCC1C(CC(=O)C1CCCCCCC(=O)O)O)O)(F)F
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| InChi Key |
PNVYHTHOCKTJCO-JOCBIADPSA-N
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| InChi Code |
InChI=1S/C20H34F2O5/c1-2-3-12-20(21,22)18(25)11-10-15-14(16(23)13-17(15)24)8-6-4-5-7-9-19(26)27/h14-15,17-18,24-25H,2-13H2,1H3,(H,26,27)/t14-,15-,17-,18-/m1/s1
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| Chemical Name |
7-[(1R,2R,3R)-2-[(3R)-4,4-difluoro-3-hydroxyoctyl]-3-hydroxy-5-oxocyclopentyl]heptanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5479 mL | 12.7395 mL | 25.4790 mL | |
| 5 mM | 0.5096 mL | 2.5479 mL | 5.0958 mL | |
| 10 mM | 0.2548 mL | 1.2740 mL | 2.5479 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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