Picosulfuric acid

Identification

Name
Picosulfuric acid
Accession Number
DB09268
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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 437.44
Monoisotopic: 437.023908795
Chemical Formula
C18H15NO8S2
Synonyms
  • Picosulfate
  • Picosulphate

Pharmacology

Pharmacology
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Indication

Indicated for cleansing of the colon as a preparation for colonoscopy in adults Label.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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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.

Hover over products below to view reaction partners

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.

Adverse Effects
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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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Picosulfuric acid.
Acetyl sulfisoxazoleThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
AcrivastinePicosulfuric acid may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Interactions
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Food Interactions
  • Avoid alcohol.
  • Avoid solid foods. When using picosulfuric acid in preparation for a colonoscopy, only consume clear fluids the day before the procedure.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Sodium picosulfate monohydrateLR57574HN81307301-38-7FHYUVJHZGPGDSP-UHFFFAOYSA-L
Sodium picosulphate anhydrousVW106606Y810040-45-6GOZDTZWAMGHLDY-UHFFFAOYSA-L
Active Moieties
NameKindUNIICASInChI Key
DeacetylbisacodylunknownR09078E41Y603-41-8LJROKJGQSPMTKB-UHFFFAOYSA-N
International/Other Brands
Guttalax / Laxoberal / Laxoberon / Picolax / Picoprep
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Skilax Drops 7.5mg/mlSolution / dropsOralMILRIN PHARMACEUTICAL CO. (M) SDN BHD2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AGAROLSodium picosulfate monohydrate (33.34 mg) + Mineral oil (28.22 mg)EmulsionOral2018-06-22Not applicableColombia flag
CitracleenSodium picosulfate monohydrate (10 mg) + Citric acid (10.97 g) + Magnesium oxide (3.5 g)Powder, for solutionOralLaboratorios Casen Fleet, S.L.U.Not applicableNot applicableCanada flag
CITRAFLEET 0.01 G/ 3.50 G/ 10.97 G ORAL ÇÖZELTI HAZIRLAMAK IÇIN TOZ IÇEREN SAŞE , 2 ADETSodium picosulfate monohydrate (0.01 g) + Citric acid (10.97 g) + Magnesium oxide (3.5 g)Powder, for solutionOralRECORDATİ İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ClenpiqSodium picosulfate monohydrate (10 mg/160mL) + Citric acid (12 g/160mL) + Magnesium oxide (3.5 g/160mL)LiquidOralASM Aerosol-Service AG2017-11-28Not applicableUS flag
ClenpiqSodium picosulfate monohydrate (10 mg/160mL) + Citric acid (12 g/160mL) + Magnesium oxide (3.5 g/160mL)LiquidOralFerring Pharmaceuticals Inc.2018-06-29Not applicableUS flag
Oral PurgativeSodium picosulfate monohydrate (10 mg) + Citric acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralOdan Laboratories Ltd2011-11-162017-06-22Canada flag
Pico-salaxSodium picosulfate monohydrate (10 mg) + Citric acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralFerring Pharmaceuticals2004-11-25Not applicableCanada flag
PICO-SALAX Powder for Oral SolutionSodium picosulfate monohydrate (10 mg) + Citric acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralFerring Sdn. Bhd.2020-09-08Not applicableMalaysia flag
PicodanSodium picosulfate monohydrate (10 mg) + Citric acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralOdan Laboratories Ltd2007-10-172012-12-31Canada flag
PicofloSodium picosulfate monohydrate (10 mg) + Citric acid (12 g) + Magnesium oxide (3.5 g)Powder, for solutionOralPharmascience Inc2011-03-25Not applicableCanada flag

Categories

ATC Codes
A06AB08 — Sodium picosulfateA06AB58 — Sodium picosulfate, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteromonocyclic compound / Arylsulfate / Azacycle / Diphenylmethane / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic sulfuric acid or derivatives
show 10 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
95D580798S
CAS number
10040-34-3
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

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]
PubChem Compound
5243
PubChem Substance
310265163
ChemSpider
5053
RxNav
1546457
ChEMBL
CHEMBL1741134
ZINC
ZINC000003873921
Wikipedia
Sodium_picosulfate
FDA label
Download (163 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentPatients Undergoing Elective Colonoscopy1
4CompletedNot AvailableBowel preparation therapy1
4CompletedNot AvailableBowel preparation therapy / Colonoscopy1
4CompletedDiagnosticColonoscopy2
4CompletedDiagnosticHemodynamics / Hyponatremia1
4CompletedScreeningColorectal Cancers1
4CompletedTreatmentCathartic Colon1
4CompletedTreatmentColon Cleansing1
4CompletedTreatmentColon Cleansing for Colonoscopy1
4CompletedTreatmentColonoscopy3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelOral
EmulsionOral
SuspensionOral
Powder, for solutionOral
LiquidOral
Capsule, liquid filledOral
Capsule, gelatin coated
Tablet, chewableOral
Tablet, effervescent
Solution / dropsOral
Solution / drops; suspension / drops
Capsule2.5 mg
Powder, meteredOral
Capsule
Powder
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8450338No2013-05-282028-10-10US flag
US8481083No2013-07-092028-10-10US flag
US9827231No2017-11-282034-06-23US flag
US10624879No2014-06-232034-06-23US flag

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

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 28, 2015 03:06 / Updated on June 13, 2020 16:24