Picosulfuric acid

Identification

Summary

Picosulfuric acid is a stimulant laxative used for cleansing of the colon as a preparation for colonoscopy in adults.

Brand Names
Clenpiq, Pico-salax, Picoflo, Purg-odan
Generic Name
Picosulfuric acid
DrugBank Accession Number
DB09268
Background

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.3

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

Pharmacology

Indication

Sodium picosulfate, in combination with magnesium oxide and anhydrous citric acid, is indicated for cleansing of the colon as a preparation for colonoscopy in adults and pediatric patients ages 9 years and older.4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofConstipation••• •••••••••• ••••••••
Treatment ofConstipation••••••••••••••••• ••••••• •• ••• •••••••••••••••• ••••••••
Treatment ofConstipation•••••••••••••••• ••••••••••••
Treatment ofConstipation••••••••••••••••••••••••••••
Treatment ofConstipation•••••••••••••••
Associated Therapies
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.3

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.2 It is hydrolyzed by colonic bacterial enzyme, sulfatase 2, to form an active metabolite bis-(p-hydroxy-phenyl)-pyridyl-2-methane (BHPM), which acts directly on the colonic mucosa to stimulate colonic peristalsis.4

Absorption

After the first dose of an oral sodium picosulfate, magnesium oxide, and anhydrous citric acid product, healthy volunteers had a picosulfate mean peak plasma concentration (Cmax) of 2.3 ng/mL that was reached at 2 hours (tmax). After the administration of two doses separated by 6 hours, the mean Cmax for picosulfate was 3.2 ng/mL, with a tmax of 7 hours.4,5

Volume of distribution

Not available.

Protein binding

Not available.

Metabolism

Sodium picosulfate is hydrolyzed by colonic bacteria to form an active metabolite bis-(p-hydroxy-phenyl)-pyridyl-2-methane (BHPM).4

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Route of elimination

Sodium picosulfate and its metabolite bis-(p-hydroxy-phenyl)-pyridyl-2-methane (BHPM) are mainly excreted in urine. The majority of BHPM is excreted as a glucuronide-conjugate. Approximately 0.1% of the sodium picosulfate dose is excreted unchanged in urine.4

Half-life

The terminal half-life of sodium picosulfate is 7.4 hours in adults and 7 hours in pediatric patients.4

Clearance

Not available.

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.4 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

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 dehydration can be increased when Acetazolamide is combined with Picosulfuric acid.
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

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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)EmulsionOralCOASPHARMA S.A.S.2018-06-22Not applicableColombia flag
CitracleenSodium picosulfate monohydrate (10 mg / 15.08 g) + Citric acid (10.97 g / 15.08 g) + Magnesium oxide (3.5 g / 15.08 g)Powder, for solutionOralLaboratorios Casen Fleet, S.L.U.Not applicableNot applicableCanada flag
CITRAFLEETSodium picosulfate monohydrate (10 mg/15.08g) + Citric acid (10.97 mg/15.08g) + Magnesium oxide (3.5 g/15.08g)Powder, for solutionOralCasen Recordati Sl2014-07-08Not applicableItaly flag
CITRAFLEETSodium picosulfate monohydrate (10 mg/15.08g) + Citric acid (10.97 mg/15.08g) + Magnesium oxide (3.5 g/15.08g)Powder, for solutionOralCasen Recordati Sl2014-07-08Not applicableItaly 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.2017-06-04Not applicableTurkey 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
Affected organisms
  • Humans and other mammals

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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. FDA Approved Drug Products: CLENPIQ (sodium picosulfate, magnesium oxide, and anhydrous citric acid) oral solution [Link]
  5. FDA Clinical Pharmacology and Biopharmaceutical Review(s) on PICOPREP [File]
Human Metabolome Database
HMDB0256534
PubChem Compound
5243
PubChem Substance
310265163
ChemSpider
5053
RxNav
1546457
ChEMBL
CHEMBL1741134
ZINC
ZINC000003873921
Wikipedia
Sodium_picosulfate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentPatients Undergoing Elective Colonoscopy1
4CompletedNot AvailableBowel preparation therapy1
4CompletedNot AvailableBowel preparation therapy / Colonoscopy1
4CompletedDiagnosticColonoscopy2
4CompletedDiagnosticHemodynamics / Hyponatremia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelOral36 mg/100ml
EmulsionOral
SuspensionOral
LiquidOral
Capsule, liquid filledOral2.5 mg
Capsule, gelatin coated
Capsule, gelatin coated2.5 mg
Solution / dropsOral750 MG/100ML
Tablet, chewableOral3.5 MG
Tablet, chewableOral
Tablet, effervescent
Solution / dropsOral
Solution / dropsOral7.5 MG/ML
Solution / drops; suspension / drops
SolutionOral750.000 mg
TabletOral5.00 mg
Capsule2.5 mg
Powder, for solutionOral
Powder, for solutionOral12 g
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
US10624879No2020-04-212034-06-23US flag
US11191753No2021-12-072034-06-23US 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, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1000900000-290835f734b1513174c6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0001900000-f22ec8b31d22b339fe91
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-3000900000-f3953bd89219b6546c81
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-059f-0029800000-6730344d48e522ae4caf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-e8a96f42272b50398b41
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0195000000-805be934072f6e0f85b5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-222.3631149
predicted
DarkChem Lite v0.1.0
[M-H]-189.58849
predicted
DeepCCS 1.0 (2019)
[M+H]+222.5293149
predicted
DarkChem Lite v0.1.0
[M+H]+191.94647
predicted
DeepCCS 1.0 (2019)
[M+Na]+222.6128149
predicted
DarkChem Lite v0.1.0
[M+Na]+198.03963
predicted
DeepCCS 1.0 (2019)

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. [Article]

Drug created at October 28, 2015 03:06 / Updated at November 08, 2022 23:43