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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Picosulfuric acid (DB09268)

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Synonyms

• Picosulfate
• Picosulphate

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Sodium picosulfate monohydrate	LR57574HN8	1307301-38-7	FHYUVJHZGPGDSP-UHFFFAOYSA-L
Sodium picosulphate anhydrous	VW106606Y8	10040-45-6	GOZDTZWAMGHLDY-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 monohydrate (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
Clenpiq	Sodium picosulfate monohydrate (10 mg/160mL) + Citric Acid (12 g/160mL) + Magnesium oxide (3.5 g/160mL)	Liquid	Oral	Ferring Pharmaceuticals Inc.	2017-11-28	Not applicable
Oral Purgative	Sodium picosulfate monohydrate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)	Powder, for solution	Oral	Odan Laboratories Ltd	2011-11-16	2017-06-22
Pico-salax	Sodium picosulfate monohydrate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)	Powder, for solution	Oral	Ferring Pharmaceuticals	2004-11-25	Not applicable
Picodan	Sodium picosulfate monohydrate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)	Powder, for solution	Oral	Odan Laboratories Ltd	2007-10-17	2012-12-31
Picoflo	Sodium picosulfate monohydrate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)	Powder, for solution	Oral	Pharmascience Inc	2011-03-25	Not applicable
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
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
Purg-odan	Sodium picosulfate monohydrate (10 mg) + Citric Acid (12 g) + Magnesium oxide (3.5 g)	Powder, for solution	Oral	Odan Laboratories Ltd	2009-02-16	Not applicable

International/Other Brands

Guttalax / Laxoberal / Laxoberon / Namilax / Pico-Salax / Picolax / Picoprep / Prepopik / Purg-Odan / Sodipic Picofast

Categories

• Acids, Acyclic
• Alimentary Tract and Metabolism
• Contact Laxatives
• Drugs for Constipation
• Gastrointestinal Agents
• Laxatives
• Pyridines
• Tricarboxylic Acids

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

• Bowel preparation therapy

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

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
6-Deoxyerythronolide B	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with 6-Deoxyerythronolide B.
Abacavir	Abacavir may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Acarbose	Acarbose may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Acetazolamide	The risk or severity of adverse effects can be increased when Acetazolamide is combined with Picosulfuric acid.
Acetyl sulfisoxazole	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Picosulfuric acid which could result in a higher serum level.
Aclidinium	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Aclidinium.

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, combinations

• A06AB — Contact laxatives
• A06A — DRUGS FOR CONSTIPATION
• A06 — DRUGS FOR CONSTIPATION
• A — ALIMENTARY TRACT AND METABOLISM

A06AB08 — Sodium picosulfate

• 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

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Healthy Volunteers	1
1, 2	Completed	Treatment	Need for Bowel Preparation	1
2	Completed	Screening	Healthy Volunteers	1
2	Recruiting	Diagnostic	Bowel Preperation / Polyethylene Glycol With Ascorbic Acid / Sodium Picosulfate and Magnesium Citrate	1
3	Completed	Not Available	Bowel preparation therapy	1
3	Completed	Other	Bowel preparation therapy	1
3	Completed	Treatment	Bowel preparation therapy	3
3	Completed	Treatment	Colonoscopy	1
3	Completed	Treatment	Occasional Constipation	1
3	Unknown Status	Diagnostic	Colonoscopy	1
4	Active Not Recruiting	Treatment	Patients Undergoing Elective Colonoscopy	1
4	Completed	Not Available	Bowel preparation therapy	1
4	Completed	Diagnostic	Colonoscopy	2
4	Completed	Diagnostic	Hemodynamics / Hyponatremias	1
4	Completed	Treatment	Cathartic Colon	1
4	Completed	Treatment	Colonoscopy	1
4	Recruiting	Diagnostic	Bowel Preparation Solutions	1
4	Unknown Status	Treatment	Bowel Preparation Solutions / Endoscopy	1
Not Available	Completed	Not Available	Bowel Cleanliness	1
Not Available	Completed	Not Available	Colonoscopy Preparation	1
Not Available	Completed	Treatment	Inflammatory Bowel Diseases (IBD)	1
Not Available	Not Yet Recruiting	Prevention	Colostomy Stoma / Hirschprung's Disease / Ileostomy - Stoma / Inflammatory Bowel Diseases (IBD) / Intestinal Obstruction / Jejunostomy Stoma / Meconium Ileus / NEC	1
Not Available	Recruiting	Not Available	Bowel preparation therapy	1
Not Available	Recruiting	Diagnostic	Colonoscopy	1
Not Available	Unknown Status	Diagnostic	Bowel preparation therapy	1
Not Available	Withdrawn	Screening	Patients Undergoing Screening or Surveillance Colonoscopy	1

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
US8481083	No	2008-10-10	2028-10-10
US9827231	No	2014-06-23	2034-06-23

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 oxidesHydrocarbon derivatives

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Substituents

Diphenylmethane / Phenylsulfate / Arylsulfate / Phenoxy compound / Pyridine / Sulfuric acid monoester / Sulfate-ester / Sulfuric acid ester / Organic sulfuric acid or derivatives / Heteroaromatic compoundAzacycle / Organoheterocyclic compound / Hydrocarbon derivative / Organic oxide / Organopnictogen compound / Organooxygen compound / Organonitrogen compound / Organic oxygen compound / Organic nitrogen compound / Aromatic heteromonocyclic compound

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Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Drug created on October 27, 2015 21:06 / Updated on November 02, 2018 08:57