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
Thumb
Synonyms
  • Picosulfate
  • Picosulphate
Product Ingredients
IngredientUNIICASInChI Key
Sodium picosulfateVW106606Y810040-45-6GOZDTZWAMGHLDY-UHFFFAOYSA-L
Sodium picosulfate monohydrateLR57574HN81307301-38-7FHYUVJHZGPGDSP-UHFFFAOYSA-L
Active Moieties
NameKindUNIICASInChI Key
DeacetylbisacodylunknownR09078E41Y603-41-8LJROKJGQSPMTKB-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CitracleenSodium picosulfate (10 mg) + Citric Acid (10.97 g) + Magnesium oxide (3.5 g)Powder, for solutionOralLaboratorios Casen Fleet, S.L.U.Not applicableNot applicableCanada
ClenpiqSodium picosulfate monohydrate (10 mg/160mL) + Citric Acid (12 g/160mL) + Magnesium oxide (3.5 g/160mL)LiquidOralFerring Pharmaceuticals2017-11-28Not applicableUs
Oral PurgativeSodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralOdan Laboratories Ltd2011-11-162017-06-22Canada
Pico-salaxSodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralFerring Pharmaceuticals2004-11-25Not applicableCanada
PicodanSodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralOdan Laboratories Ltd2007-10-172012-12-31Canada
PicofloSodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralPharmascience Inc2011-03-25Not applicableCanada
PrepopikSodium picosulfate monohydrate (10 mg/16.2g) + Citric Acid (12 g/16.2g) + Magnesium oxide (3.5 g/16.2g)Powder, meteredOralFerring Pharmaceuticals Inc.2014-09-05Not applicableUs
PrepopikSodium picosulfate monohydrate (10 mg/16.1g) + Citric Acid (12 g/16.1g) + Magnesium oxide (3.5 g/16.1g)Powder, meteredOralFerring Pharmaceuticals Inc.2012-07-16Not applicableUs
Purg-odanSodium picosulfate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralOdan Laboratories Ltd2009-02-16Not applicableCanada
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
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AgmatineThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Agmatine.
AlprazolamAlprazolam may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Aluminum hydroxideThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Aluminum hydroxide.
AmdinocillinThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amdinocillin.
AmikacinThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amikacin.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Picosulfuric acid.
Aminosalicylic AcidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Aminosalicylic Acid.
AmiodaroneThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amiodarone.
Food Interactions
Not Available

References

General References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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, combinationsA06AB08 — Sodium picosulfate
FDA label
Download (163 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedTreatmentNeed for Bowel Preparation1
2CompletedScreeningHealthy Volunteers1
2RecruitingDiagnosticBowel Preperation / Polyethylene Glycol With Ascorbic Acid / Sodium Picosulfate and Magnesium Citrate1
3CompletedNot AvailableBowel preparation therapy1
3CompletedOtherBowel preparation therapy1
3CompletedTreatmentBowel preparation therapy3
3CompletedTreatmentColonoscopy1
3CompletedTreatmentOccasional Constipation1
3Unknown StatusDiagnosticColonoscopy1
4Active Not RecruitingTreatmentPatients Undergoing Elective Colonoscopy1
4CompletedNot AvailableBowel preparation therapy1
4CompletedDiagnosticColonoscopy2
4CompletedDiagnosticHemodynamics / Hyponatremias1
4CompletedTreatmentCathartic Colon1
4CompletedTreatmentColonoscopy1
4Not Yet RecruitingDiagnosticBowel Preparation Solutions1
4Unknown StatusTreatmentBowel Preparation Solutions / Endoscopy1
Not AvailableCompletedNot AvailableBowel Cleanliness1
Not AvailableCompletedNot AvailableColonoscopy Preparation1
Not AvailableCompletedTreatmentInflammatory Bowel Diseases (IBD)1
Not AvailableNot Yet RecruitingPreventionColostomy Stoma / Hirschprung's Disease / Ileostomy - Stoma / Inflammatory Bowel Diseases (IBD) / Intestinal Obstruction / Jejunostomy Stoma / Meconium Ileus / NEC1
Not AvailableRecruitingNot AvailableBowel preparation therapy1
Not AvailableRecruitingDiagnosticColonoscopy1
Not AvailableUnknown StatusDiagnosticBowel preparation therapy1
Not AvailableWithdrawnScreeningPatients Undergoing Screening or Surveillance Colonoscopy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidOral
Powder, for solutionOral
Powder, meteredOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8450338No2008-10-102028-10-10Us
US8481083No2008-10-102028-10-10Us
US9827231No2014-06-232034-06-23Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0185 mg/mLALOGPS
logP-0.05ALOGPS
logP-1.5ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)-2.5ChemAxon
pKa (Strongest Basic)4.08ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area140.09 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity101.83 m3·mol-1ChemAxon
Polarizability40.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
  1. 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