Picosulfuric acid
Identification
- Name
- Picosulfuric acid
- Accession Number
- DB09268
- Type
- Small Molecule
- Groups
- Approved
- Description
Picosulfuric acid is found in laxative products. Sodium picosulfate is a used to treat constipation or induce colon cleansing to prepare the large bowels before colonoscopy or surgery. The combination product containing sodium picosulfate and magnesium citrate was introduced to the Canadian market in 2005 and has been used in European countries for many years [4].
- Structure
Structure for Picosulfuric acid (DB09268)
- Synonyms
- Picosulfate
- Picosulphate
- Product Ingredients
Ingredient UNII CAS InChI Key Sodium picosulfate VW106606Y8 10040-45-6 GOZDTZWAMGHLDY-UHFFFAOYSA-L Sodium picosulfate monohydrate LR57574HN8 1307301-38-7 FHYUVJHZGPGDSP-UHFFFAOYSA-L - Active Moieties
Name Kind UNII CAS InChI Key Deacetylbisacodyl unknown R09078E41Y 603-41-8 LJROKJGQSPMTKB-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Citracleen Sodium picosulfate (10 mg) + Citric Acid (10.97 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Laboratorios Casen Fleet, S.L.U. Not applicable Not applicable Canada 
Clenpiq Sodium picosulfate monohydrate (10 mg/160mL) + Citric Acid (12 g/160mL) + Magnesium oxide (3.5 g/160mL) Liquid Oral Ferring Pharmaceuticals 2017-11-28 Not applicable US 
Oral Purgative Sodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Odan Laboratories Ltd 2011-11-16 2017-06-22 Canada Pico-salax Sodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Ferring Pharmaceuticals 2004-11-25 Not applicable Canada Picodan Sodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Odan Laboratories Ltd 2007-10-17 2012-12-31 Canada Picoflo Sodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Pharmascience Inc 2011-03-25 Not applicable Canada Prepopik Sodium picosulfate monohydrate (10 mg/16.2g) + Citric Acid (12 g/16.2g) + Magnesium oxide (3.5 g/16.2g) Powder, metered Oral Ferring Pharmaceuticals Inc. 2014-09-05 Not applicable US Prepopik Sodium picosulfate monohydrate (10 mg/16.1g) + Citric Acid (12 g/16.1g) + Magnesium oxide (3.5 g/16.1g) Powder, metered Oral Ferring Pharmaceuticals Inc. 2012-07-16 Not applicable US Purg-odan Sodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g) Powder, for solution Oral Odan Laboratories Ltd 2009-02-16 Not applicable Canada - International/Other Brands
- Guttalax / Laxoberal / Laxoberon / Namilax / Pico-Salax / Picolax / Picoprep / Prepopik / Purg-Odan / Sodipic Picofast
- Categories
- UNII
- 95D580798S
- CAS number
- 10040-34-3
- Weight
- Average: 437.44
Monoisotopic: 437.023908795 - Chemical Formula
- C18H15NO8S2
- InChI Key
- UJIDKYTZIQTXPM-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H15NO8S2/c20-28(21,22)26-15-8-4-13(5-9-15)18(17-3-1-2-12-19-17)14-6-10-16(11-7-14)27-29(23,24)25/h1-12,18H,(H,20,21,22)(H,23,24,25)
- IUPAC Name
- {4-[(pyridin-2-yl)[4-(sulfooxy)phenyl]methyl]phenyl}oxidanesulfonic acid
- SMILES
- OS(=O)(=O)OC1=CC=C(C=C1)C(C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=N1
Pharmacology
- Indication
Indicated for cleansing of the colon as a preparation for colonoscopy in adults [Label].
- Associated Therapies
- Pharmacodynamics
Sodium picosulfate is a stimulant laxative that in conjunction with magnesium citrate, produces a purgative effect on stools. In a multicentre, observational study comprising of patients undergoing colonoscopy, more than 93.0% of the patients receiving sodium picosulfate-containing preparations reported the colon cleansing effect to be effective [4].
- Mechanism of action
Picosulfuric acid, as sodium picosulfate, is a contact laxative. Sodium picosulfate inhibits the absorption of water and electrolytes, and increases their secretion into the intestinal lumen [3]. It is hydrolyzed by colonic bacterial enzyme, sulfatase [3], to form an active metabolite bis-(p-hydroxy-phenyl)-pyridyl-2-methane (BHPM), which acts directly on the colonic mucosa to stimulate colonic peristalsis [Label].
- Absorption
In healthy volunteers receiving 2 packets of sodium picosulfate in combination with magnesium oxide and anhydrous citric acid every 6 hours, the mean peak plasma concentrations (Cmax) of sodium picosulfate was achieved within 7 hours (Tmax) [Label]. The mean Cmax of its active metabolite, BHPM, was 0.05 ng/mL [Label].
- Volume of distribution
No pharmacokinetic data is available for picosulfuric acid.
- Protein binding
No pharmacokinetic data is available for picosulfuric acid.
- Metabolism
Sodium picosulfate is hydrolyzed by colonic bacteria to form an active metabolite bis-(p-hydroxy-phenyl)-pyridyl-2-methane (BHPM) [Label].
- Route of elimination
Sodium picosulfate and its metabolite BHPM are mainly excreted in urine. The fraction of the absorbed sodium picosulfate dose excreted in urine as unchanged parent compound was 0.19% [Label]. Urinary recovery of BHPM was 0.01% of total administered drug [Label]. A small amount absorbed picosulfate is reported to be excreted in the urine as a glucuronide-conjugate of BHPM [5].
- Half life
The terminal half-life of sodium picosulfate was 7.4 hours [Label].
- Clearance
No pharmacokinetic data is available for picosulfuric acid.
- Toxicity
Overdosage of laxative preparations containing sodium picosulfate may lead to severe electrolyte disturbances, in addition to dehydration and hypovolemia, with signs and symptoms of these disturbances. In case of overdose, monitor for fluid and electrolyte disturbances with symptomatic treatment [Label]. In vitro, 800 and 1600 mg/mL of sodium picosulfate exerted cytotoxic effects on cultured liver cells by inducing dose-dependent vacuolic and fatty change, as well as necrosis combined with a lowered mitotic activity and a slight increase in LDH values of the rapidly growing cultured liver cells of rabbit [1].
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Acetaminophen Acetaminophen may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level. Agmatine The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Agmatine. Alprazolam Alprazolam may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level. Aluminum hydroxide The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Aluminum hydroxide. Amdinocillin The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amdinocillin. Amikacin The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amikacin. Amiloride The risk or severity of adverse effects can be increased when Amiloride is combined with Picosulfuric acid. Aminosalicylic Acid The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Aminosalicylic Acid. Amiodarone The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amiodarone. - Food Interactions
- Not Available
References
- General References
- Nishikawa J, Kast A: Toxicity study with sodium picosulfate in cultured liver cells of rabbit, rat and man. Arzneimittelforschung. 1981;31(2):321-5. [PubMed:7194649]
- Jauch R, Hammer R, Busch U, Kopitar Z, Ohnuma N, Niki T: [Pharmacokinetics and metabolism of sodium picosulfate in the rat (author's transl)]. Arzneimittelforschung. 1977;27(5):1045-50. [PubMed:577869]
- Kim DH, Hyun SH, Shim SB, Kobashi K: The role of intestinal bacteria in the transformation of sodium picosulfate. Jpn J Pharmacol. 1992 May;59(1):1-5. [PubMed:1507649]
- Love J, Bernard EJ, Cockeram A, Cohen L, Fishman M, Gray J, Morgan D: A multicentre, observational study of sodium picosulfate and magnesium citrate as a precolonoscopy bowel preparation. Can J Gastroenterol. 2009 Oct;23(10):706-10. [PubMed:19826647]
- FDA Clinical Pharmacology and Biopharmaceutical Review(s) on PICOPREP [File]
- External Links
- PubChem Compound
- 5243
- PubChem Substance
- 310265163
- ChemSpider
- 5053
- ChEMBL
- CHEMBL1741134
- Wikipedia
- Sodium_picosulfate
- ATC Codes
- A06AB58 — Sodium picosulfate, combinations
- A06AB — Contact laxatives
- A06A — DRUGS FOR CONSTIPATION
- A06 — DRUGS FOR CONSTIPATION
- A — ALIMENTARY TRACT AND METABOLISM
- FDA label
- Download (163 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Liquid Oral Powder, for solution Oral Powder, metered Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US8450338 No 2008-10-10 2028-10-10 US US8481083 No 2008-10-10 2028-10-10 US US9827231 No 2014-06-23 2034-06-23 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0185 mg/mL ALOGPS logP -0.05 ALOGPS logP -1.5 ChemAxon logS -4.4 ALOGPS pKa (Strongest Acidic) -2.5 ChemAxon pKa (Strongest Basic) 4.08 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 140.09 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 101.83 m3·mol-1 ChemAxon Polarizability 40.3 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenylsulfates / Phenoxy compounds / Sulfuric acid monoesters / Pyridines and derivatives / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Diphenylmethane / Phenylsulfate / Arylsulfate / Phenoxy compound / Pyridine / Sulfuric acid monoester / Sulfate-ester / Sulfuric acid ester / Organic sulfuric acid or derivatives / Heteroaromatic compound show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
Enzymes
- Kind
- Protein
- Organism
- Escherichia coli O1:K1 / APEC
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the transfer of sulfuryl groups between phenolic compounds.
- Specific Function
- Aryl sulfotransferase activity
- Gene Name
- assT
- Uniprot ID
- A0A0H2Z368
- Uniprot Name
- Arylsulfate sulfotransferase AssT
- Molecular Weight
- 66545.805 Da
References
- Kim DH, Hyun SH, Shim SB, Kobashi K: The role of intestinal bacteria in the transformation of sodium picosulfate. Jpn J Pharmacol. 1992 May;59(1):1-5. [PubMed:1507649]
Drug created on October 27, 2015 21:06 / Updated on September 23, 2018 18:11