Pantoprazole

Identification

Summary

Pantoprazole is a proton pump inhibitor used to treat erosive esophagitis, gastric acid hypersecretion, and to promote healing of tissue damage caused by gastric acid.

Brand Names
Protonix, Somac Control, Tecta
Generic Name
Pantoprazole
DrugBank Accession Number
DB00213
Background

Pantoprazole is a first-generation proton pump inhibitor (PPI) used for the management of gastroesophageal reflux disease (GERD), for gastric protection to prevent recurrence of stomach ulcers or gastric damage from chronic use of NSAIDs, and for the treatment of pathological hypersecretory conditions including Zollinger-Ellison (ZE) Syndrome. It can also be found in quadruple regimens for the treatment of H. pylori infections along with other antibiotics including amoxicillin, clarithromycin, and metronidazole, for example.1023 Its efficacy is considered similar to other medications within the PPI class including omeprazole, esomeprazole, lansoprazole, dexlansoprazole, and rabeprazole.

Pantoprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cell. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of pantoprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, pantoprazole's duration of antisecretory effect persists longer than 24 hours.Label

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as pantoprazole have been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients including iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.12

PPIs such as pantoprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.14,15

Pantoprazole doses should be slowly lowered, or tapered, before discontinuing as rapid discontinuation of PPIs such as pantoprazole may cause a rebound effect and a short term increase in hypersecretion.13

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 383.37
Monoisotopic: 383.075133083
Chemical Formula
C16H15F2N3O4S
Synonyms
  • Pantoprazol
  • Pantoprazole
  • Pantoprazolum

Pharmacology

Indication

Pantoprazole Injection:

Treatment of gastroesophageal reflux disease associated with a history of erosive esophagitis

Pantoprazole for injection is indicated for short-term treatment (7-10 days) of patients having gastroesophageal reflux disease (GERD) with a history of erosive esophagitis, as an alternative to oral medication in patients who are unable to continue taking pantoprazole delayed-release tablets. Safety and efficacy of pantoprazole injection as the initial treatment of patients having GERD with a history of erosive esophagitis have not been demonstrated at this time.Label

Pathological Hypersecretion Associated with Zollinger-Ellison Syndrome

Pantoprazole for injection is indicated for the treatment of pathological hypersecretory conditions associated with Zollinger-Ellison Syndrome or other neoplastic conditions.Label

Pantoprazole delayed-release oral suspension:

Short-Term Treatment of erosive esophagitis associated with gastroesophageal reflux disease (GERD)

Indicated in adults and pediatric patients five years of age and above for the short-term treatment (up to 8 weeks) in the healing and symptomatic relief of erosive esophagitis. For adult patients who have not healed after 8 weeks of treatment, an additional 8-week course of pantoprazole may be considered. Safety of treatment beyond 8 weeks in pediatric patients has not been determined.19

Maintenance of healing of erosive esophagitis

Indicated for maintenance of healing of erosive esophagitis and reduction in relapse rates of daytime and nighttime heartburn symptoms in adult patients with GERD.19

Pathological hypersecretory conditions including Zollinger-Ellison syndrome

Indicated for the long-term treatment of the above conditions.19

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofErosive esophagitis••••••••••••
Treatment ofErosive esophagitis••••••••••••
Treatment ofErosive esophagitis••••••••••••
Treatment ofGerd••••••••••••
Treatment ofGerd with erosive esophagitis•••••••••••••••••••• ••• ••• •••••• •• •••••••• •••••• •••••••••••• ••••••••••••••• •••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

This drug acts to decrease gastric acid secretion, which reduces stomach acidity. Pantoprazole administration leads to long-lasting inhibition of gastric acid secretion.16

General Effects

Pantoprazole has been shown to reduce acid reflux-related symptoms, heal inflammation of the esophagus, and improve patient quality of life more effectively than histamine-2 receptor antagonists (H2 blockers). This drug has an excellent safety profile and a low incidence of drug interactions. It can be used safely in various high-risk patient populations, including the elderly and those with renal failure or moderate hepatic dysfunction.1

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as pantoprazole have been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients including iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.12

PPIs such as pantoprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes 14,15.

A note on laboratory testing abnormalities

During treatment with antisecretory medicinal products such as pantoprazole, serum gastrin (a peptide hormone that stimulates secretion of gastric acid) increases in response to the decreased acid secretion caused by proton pump inhibition. The increased gastrin level may interfere with investigations for neuroendocrine tumors. Published evidence suggests that proton pump inhibitors should be stopped 14 days before chromogranin A (CgA) measurements. This permits chromogranin A levels, that might be falsely elevated after proton pump inhibitor treatment, to return to the normal reference range.21

Reports have been made of false-positive results in urine screening tests for tetrahydrocannabinol (THC) in patients receiving the majority of proton pump inhibitors, including pantoprazole. A confirmatory method should be used.21

Mechanism of action

Hydrochloric acid (HCl) secretion into the gastric lumen is a process regulated mainly by the H(+)/K(+)-ATPase of the proton pump, expressed in high quantities by the parietal cells of the stomach.9 ATPase is an enzyme on the parietal cell membrane that facilitates hydrogen and potassium exchange through the cell, which normally results in the extrusion of potassium and formation of HCl (gastric acid).

Proton pump inhibitors such as pantoprazole are substituted benzimidazole derivatives, weak bases, which accumulate in the acidic space of the parietal cell before being converted in the canaliculi (small canal) of the gastric parietal cell, an acidic environment, to active sulfenamide derivatives. This active form then makes disulfide bonds with important cysteines on the gastric acid pump, inhibiting its function.6 Specifically, pantoprazole binds to the sulfhydryl group of H+, K+-ATPase, which is an enzyme implicated in accelerating the final step in the acid secretion pathway. The enzyme is inactivated, inhibiting gastric acid secretion.7 The inhibition of gastric acid secretion is stronger with proton pump inhibitors such as pantoprazole and lasts longer than with the H(2) antagonists.9

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Humans
NN(G),N(G)-dimethylarginine dimethylaminohydrolase 1
inhibitor
Humans
Absorption

Pantoprazole is absorbed after oral administration as an enteric-coated tablet with maximum plasma concentrations attained within 2 – 3 hours and a bioavailability of 77% that does not change with multiple dosing 6. Following an oral dose of 40mg, the Cmax is approximately 2.5 μg/mL with a tmax of 2 to 3 hours. The AUC is approximately 5 μg.h/mL. There is no food effect on AUC (bioavailability) and Cmax.22

Delayed-release tablets are prepared as enteric-coated tablets so that absorption of pantoprazole begins only after the tablet leaves the stomach.

Volume of distribution

The apparent volume of distribution of pantoprazole is approximately 11.0-23.6 L, distributing mainly in the extracellular fluid.Label

Protein binding

Approximately 98%Label

Metabolism

Pantoprazole is heavily metabolized in the liver by the cytochrome P450 (CYP) system. Pantoprazole metabolism is independent of the route of administration (intravenous or oral). The main metabolic pathway is demethylation, by CYP2C19 hepatic cytochrome enzyme, followed by sulfation; other metabolic pathways include oxidation by CYP3A4. There is no evidence that any of the pantoprazole metabolites are pharmacologically active.19

After hepatic metabolism, almost 80% of an oral or intravenous dose is excreted as metabolites in urine; the remainder is found in feces and originates from biliary secretion.8

Hover over products below to view reaction partners

Route of elimination

After a single oral or intravenous (IV) dose of 14C-labeled pantoprazole to healthy, normal metabolizing subjects, about 71% of the dose was excreted in the urine, with 18% excreted in the feces by biliary excretion. There was no kidney excretion of unchanged pantoprazole.19

Half-life

About 1 hour19

Clearance

Adults: With intravenous administration of pantoprazole to extensive metabolizers, total clearance is 7.6-14.0 L/h.16 In a population pharmacokinetic analysis, the total clearance increased with increasing body weight in a non-linear fashion.16

Children: clearance values in the children 1 to 5 years old with endoscopically proven GERD had a median value of 2.4 L/h.19

Adverse Effects
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Toxicity

Rat Oral LD 50 747 mg/kg17

Tumorigenicity

Because of the chronic nature of GERD, there may be a potential for long-term administration of pantoprazole. In long-term rodent studies, pantoprazole was carcinogenic and its administration lead to rare types of gastrointestinal tumors. The relevance of these findings to tumor development in humans is unknown at this time.19

Teratogenic Effects

This drug falls under pregnancy category B category. Reproduction studies have been performed in rats at oral doses up to 88 times the recommended human dose (RHD), as well as in rabbits at oral doses up to 16 times the RHD, and have shown no evidence of impaired fertility or harm to the fetus caused by pantoprazole. No adequate and well-controlled studies in pregnant women have been completed. Because animal reproduction studies are not always predictive of human response, this drug should only be used during pregnancy if clearly required.19

Nursing Mothers

Pantoprazole and its metabolites have been found to be excreted in the milk of rats. Pantoprazole excretion in human milk has been found in a study performed with a single nursing mother after one 40 mg oral dose. The clinical relevance of this finding is not known, however, it is advisable to take note of this finding when considering pantoprazole use during nursing. Many drugs excreted in human breastmilk have a risk for serious adverse effects in nursing infants.19

Pathways
PathwayCategory
Pantoprazole Metabolism PathwayDrug metabolism
Pantoprazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer.Details

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
AbacavirPantoprazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Pantoprazole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Pantoprazole can be increased when combined with Abatacept.
AbemaciclibPantoprazole may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Pantoprazole.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pantoprazole magnesium1AL13B11R4199387-73-0RDRUTBCDIVCMMX-UHFFFAOYSA-N
Pantoprazole magnesium dihydrateNot AvailableNot AvailableNot applicable
Pantoprazole magnesium hemipentahydrateNot AvailableNot AvailableGYTCJCWFCBALFS-UHFFFAOYSA-N
Pantoprazole sodium6871619Q5X164579-32-2BRIJTIAFXDNYOD-UHFFFAOYSA-N
Product Images
International/Other Brands
Pantozol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act PantoprazoleTablet, delayed release40 mgOralActavis Pharma Company2008-06-042018-07-09Canada flag
Controloc ControlTablet, delayed release20 mgOralTakeda2016-09-08Not applicableEU flag
Controloc ControlTablet, delayed release20 mgOralTakeda2016-09-08Not applicableEU flag
Controloc ControlTablet, delayed release20 mgOralTakeda2016-09-08Not applicableEU flag
Controloc ControlTablet, delayed release20 mgOralTakeda2016-09-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Abbott-pantoprazoleTablet, delayed release20 mgOralAbbottNot applicableNot applicableCanada flag
Abbott-pantoprazoleTablet, delayed release40 mgOralAbbott2014-03-172015-12-31Canada flag
Ag-pantoprazoleTablet, delayed release20 mgOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-pantoprazoleTablet, delayed release40 mgOralAngita Pharma Inc.2018-07-17Not applicableCanada flag
Ag-pantoprazole SodiumTablet, delayed release40 mgOralAngita Pharma Inc.2018-12-27Not applicableCanada flag

Categories

ATC Codes
A02BD04 — Pantoprazole, amoxicillin and clarithromycinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleA02BC02 — Pantoprazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Sulfinylbenzimidazoles
Direct Parent
Sulfinylbenzimidazoles
Alternative Parents
Alkyl aryl ethers / Pyridines and derivatives / Benzenoids / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, aromatic ether, sulfoxide, pyridines, benzimidazoles (CHEBI:7915)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
D8TST4O562
CAS number
102625-70-7
InChI Key
IQPSEEYGBUAQFF-UHFFFAOYSA-N
InChI
InChI=1S/C16H15F2N3O4S/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16/h3-7,15H,8H2,1-2H3,(H,20,21)
IUPAC Name
6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
SMILES
COC1=C(OC)C(CS(=O)C2=NC3=C(N2)C=C(OC(F)F)C=C3)=NC=C1

References

Synthesis Reference

Rudolf Linder, "Freeze-dried pantoprazole preparation and pantoprazole injection." U.S. Patent US20030003058, issued January 02, 2003.

US20030003058
General References
  1. Mathews S, Reid A, Tian C, Cai Q: An update on the use of pantoprazole as a treatment for gastroesophageal reflux disease. Clin Exp Gastroenterol. 2010;3:11-6. Epub 2010 Jan 20. [Article]
  2. Dabrowski A, Stabuc B, Lazebnik L: Meta-analysis of the efficacy and safety of pantoprazole in the treatment and symptom relief of patients with gastroesophageal reflux disease - PAN-STAR. Prz Gastroenterol. 2018;13(1):6-15. doi: 10.5114/pg.2018.74556. Epub 2018 Mar 26. [Article]
  3. Strand DS, Kim D, Peura DA: 25 Years of Proton Pump Inhibitors: A Comprehensive Review. Gut Liver. 2017 Jan 15;11(1):27-37. doi: 10.5009/gnl15502. [Article]
  4. Jungnickel PW: Pantoprazole: a new proton pump inhibitor. Clin Ther. 2000 Nov;22(11):1268-93. [Article]
  5. Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
  6. Bardou M, Martin J: Pantoprazole: from drug metabolism to clinical relevance. Expert Opin Drug Metab Toxicol. 2008 Apr;4(4):471-83. doi: 10.1517/17425255.4.4.471 . [Article]
  7. Shin JM, Sachs G: Differences in binding properties of two proton pump inhibitors on the gastric H+,K+-ATPase in vivo. Biochem Pharmacol. 2004 Dec 1;68(11):2117-27. doi: 10.1016/j.bcp.2004.07.035. [Article]
  8. Huber R, Hartmann M, Bliesath H, Luhmann R, Steinijans VW, Zech K: Pharmacokinetics of pantoprazole in man. Int J Clin Pharmacol Ther. 1996 May;34(1 Suppl):S7-16. [Article]
  9. Lewin MJ: Cellular mechanisms and inhibitors of gastric acid secretion. Drugs Today (Barc). 1999 Oct;35(10):743-52. [Article]
  10. Fallone CA, Chiba N, van Zanten SV, Fischbach L, Gisbert JP, Hunt RH, Jones NL, Render C, Leontiadis GI, Moayyedi P, Marshall JK: The Toronto Consensus for the Treatment of Helicobacter pylori Infection in Adults. Gastroenterology. 2016 Jul;151(1):51-69.e14. doi: 10.1053/j.gastro.2016.04.006. Epub 2016 Apr 19. [Article]
  11. Tanus-Santos JE, Pinheiro LC: Proton pump inhibitors: new mechanisms of action. Basic Clin Pharmacol Toxicol. 2019 Apr 13. doi: 10.1111/bcpt.13237. [Article]
  12. Haastrup PF, Thompson W, Sondergaard J, Jarbol DE: Side Effects of Long-Term Proton Pump Inhibitor Use: A Review. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):114-121. doi: 10.1111/bcpt.13023. Epub 2018 May 24. [Article]
  13. Reimer C, Sondergaard B, Hilsted L, Bytzer P: Proton-pump inhibitor therapy induces acid-related symptoms in healthy volunteers after withdrawal of therapy. Gastroenterology. 2009 Jul;137(1):80-7, 87.e1. doi: 10.1053/j.gastro.2009.03.058. Epub 2009 Apr 10. [Article]
  14. Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [Article]
  15. Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [Article]
  16. Pantoprazole Tablets, Monograph [File]
  17. Pfizer Safety Data Sheet [File]
  18. Assessment Report, Pantozol [File]
  19. Protonix delayed release and oral suspension FDA label [File]
  20. Pantoloc EMA label [File]
  21. Sandoz Pantoprazole DRT Monograph [File]
  22. Health Canada Label - Pantoprazole [File]
  23. TOP Guidelines - H pylori [File]
Human Metabolome Database
HMDB0005017
KEGG Drug
D05353
KEGG Compound
C11806
PubChem Compound
4679
PubChem Substance
46504622
ChemSpider
4517
BindingDB
50241342
RxNav
40790
ChEBI
7915
ChEMBL
CHEMBL1502
Therapeutic Targets Database
DAP000724
PharmGKB
PA450774
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pantoprazole
FDA label
Download (183 KB)
MSDS
Download (58.1 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Wyeth pharmaceuticals inc
  • Kudco ireland ltd
  • Sun pharma global inc
  • Teva pharmaceuticals usa inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Cardinal Health
  • Coupler Enterprises Inc.
  • Direct Pharmaceuticals Inc.
  • DispenseXpress Inc.
  • ESI Lederle
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Nycomed Inc.
  • Patheon Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
  • Wasserburger Arzneimittelwerk GmbH
  • Wyeth Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral45.100 mg
InjectionIntravenous
InjectionIntravenous40 mg
Capsule, extended releaseOral4000000 mg
Capsule, extended releaseOral40 mg
TabletOral40.000 mg
Kit; tabletOral
TabletOral40.00 mg
Tablet, delayed releaseOral
TabletOral20 mg
Injection, powder, for solution
Tablet, delayed releaseOral22.6 MG
Tablet, delayed releaseOral45.2 MG
TabletOral20.0 mg
TabletOral40.0 mg
InjectionIntravenous40 mg/ml
Tablet, film coatedOral20 mg
Tablet, film coatedOral40 mg
Tablet, delayed releaseOral20.00 mg
Injection, solutionIntravenous40 mg
Tablet, delayed releaseOral20 mg
Tablet, delayed releaseOral2000000 mg
Tablet, delayed releaseOral4000000 mg
Injection, powder, for solutionParenteral
Tablet, delayed releaseOral
Tablet, coatedOral
Tablet, coatedOral20 mg
Tablet, coatedOral40 MG
For suspensionOral40 mg/1
Injection, powder, for solutionIntravenous
Injection, powder, for solutionIntravenous40 MG
Injection, powder, for solutionIntravenous40 mg/1
Injection, powder, lyophilized, for solutionIntravenous40 mg
Injection, powder, lyophilized, for solutionIntravenous40 mg/1
Injection, powder, lyophilized, for solutionIntravenous40 mg/10mL
Injection, solutionIntravenous40 mg/100mL
Injection, solutionIntravenous40 mg/50mL
Injection, solutionIntravenous80 mg/100mL
TabletOral40 mg/1
Tablet, delayed releaseOral20 mg/1
Tablet, delayed releaseOral40 mg/1
Tablet, delayed releaseOral45.1 Mg
TabletOral
Injection, powder, for solutionParenteral40 MG
Injection, powder, for solution40 mg/1vial
TabletOral40 mg
Capsule, coatedOral40 mg
Tablet, delayed releaseOral40 mg
Tablet, delayed releaseOral22.55 MG
Injection, powder, lyophilized, for solutionIntravenous40 mg/vial
SolutionIntravenous40.000 mg
Powder, for solutionIntravenous40 mg / vial
SolutionParenteral40.000 mg
Injection, powder, lyophilized, for solutionIntravenous
Injection, powder, for solution40 mg
Granule, delayed releaseOral40 mg/1
Injection, powder, for solutionIntravenous40 mg/10mL
TabletOral20.000 mg
TabletOral43.040 mg
Tablet, film coatedOral
Powder40 mg/1vial
Prices
Unit descriptionCostUnit
Protonix iv 40 mg vial14.4USD vial
Protonix 40 mg tablet dr8.91USD tablet
Protonix 20 mg tablet5.43USD tab
Protonix 40 mg Enteric Coated Tabs5.43USD tab
Protonix dr 20 mg tablet5.22USD tablet
Protonix dr 40 mg tablet5.22USD tablet
Pantoprazole Sodium 20 mg Enteric Coated Tabs4.26USD tab
Pantoprazole Sodium 40 mg Enteric Coated Tabs4.26USD tab
Pantoprazole sod dr 20 mg tablet3.93USD tablet
Pantoprazole sod dr 40 mg tablet3.93USD tablet
Pantoloc 40 mg Enteric-Coated Tablet2.28USD tablet
Apo-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Co Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Mylan-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Novo-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Phl-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Pms-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Ran-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Ratio-Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
Sandoz Pantoprazole 40 mg Enteric-Coated Tablet1.27USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4758579No1988-07-192010-07-19US flag
CA2428870No2006-05-232021-11-17Canada flag
CA2092694No2005-04-052011-09-06Canada flag
CA2341031No2006-04-042019-08-12Canada flag
US5997903Yes1999-12-072017-06-07US flag
US8754108Yes2014-06-172022-05-17US flag
US6780881Yes2004-08-242022-05-17US flag
US7351723Yes2008-04-012022-05-17US flag
US7550153Yes2009-06-232025-03-30US flag
US7553498Yes2009-06-302025-03-30US flag
US7838027Yes2010-11-232025-03-30US flag
US7544370Yes2009-06-092026-12-07US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)149-150https://www.pfizer.com/sites/default/files/products/material_safety_data/Pantoprazo;le_sodium_for_injection_20-June-2016.pdf
boiling point (°C)586.9±60.0 °C at 760 mmHghttp://www.chemspider.com/Chemical-Structure.4517.html
water solubilityFreely soluble in water.https://www.ncbi.nlm.nih.gov/pubmed/18433349
logP2.05https://www.pfizer.com/sites/default/files/products/material_safety_data/Pantoprazo;le_sodium_for_injection_20-June-2016.pdf
pKa3.92 and 8.19https://www.ema.europa.eu/documents/assessment-report/pantozol-control-epar-public-assessment-report_en.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.495 mg/mLALOGPS
logP2.11ALOGPS
logP2.18Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.15Chemaxon
pKa (Strongest Basic)3.55Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area86.33 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity90.05 m3·mol-1Chemaxon
Polarizability35.17 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier-0.5777
Caco-2 permeable+0.7262
P-glycoprotein substrateNon-substrate0.6127
P-glycoprotein inhibitor IInhibitor0.5587
P-glycoprotein inhibitor IINon-inhibitor0.9198
Renal organic cation transporterNon-inhibitor0.6285
CYP450 2C9 substrateNon-substrate0.84
CYP450 2D6 substrateNon-substrate0.8683
CYP450 3A4 substrateSubstrate0.7254
CYP450 1A2 substrateInhibitor0.7639
CYP450 2C9 inhibitorNon-inhibitor0.8054
CYP450 2D6 inhibitorNon-inhibitor0.7308
CYP450 2C19 inhibitorInhibitor0.7877
CYP450 3A4 inhibitorNon-inhibitor0.7258
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.903
Ames testNon AMES toxic0.5527
CarcinogenicityNon-carcinogens0.8108
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.3466 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9228
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pb9-2917000000-ff97714a7048457e737c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-fdcf6f79acd06edd5401
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-51e30cd23db38362ad60
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-f102a8245343f84e3b0d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-2e08d1a0248a26126d5e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03fr-0940000000-25352b30e7648d902bc6
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-b7a2f038ef5f90fc95e1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-66cb42b0034f31368f8e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-378124c9a24c3a502e9f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-f102a8245343f84e3b0d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-5e51997385e26e7da0c1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03fr-0950000000-44836f641a9ead0cf572
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-4eb2af1f8bb7c0592920
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0900000000-8da503184069a7677ead
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-8b9e209f5ce292385d34
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0290000000-2953e2577582bbfe2ad8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-ce081988e6394cc11545
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0492000000-ad12657183be4d366241
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f79-0940000000-4c3f08a4a30021511475
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0920000000-f4a7f9db8c3b4fc1476d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-f665417f17af100e2cff
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-87b455243d8a69f87d9a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-b7fa8fc340e8423574aa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0391000000-73c186ec001abcb34f6e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f79-0940000000-ac37fdf680de7ab0411e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0920000000-aac8ca4662593728ba26
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-4a7e27a4f578c164c2b4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-d3074931054ee514dbb8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-30364d1aec50b4c1f89b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0090000000-421c0585dcef1856540f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udr-0950000000-507be5cae74281c438b7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0950000000-4a1f81f36a9c7d1304f9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0049000000-e105cca1369d693ac267
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0954000000-8fcd40d31c9ff0eaf7b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2890000000-a9eed69fb64ac365d8aa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-9820000000-bef2dcd2737ec2d9dbdc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2910000000-6712b1d35f743bd2caa4
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]-202.7193413
predicted
DarkChem Lite v0.1.0
[M-H]-187.74922
predicted
DeepCCS 1.0 (2019)
[M+H]+202.5185413
predicted
DarkChem Lite v0.1.0
[M+H]+190.10724
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.9481413
predicted
DarkChem Lite v0.1.0
[M+Na]+197.15103
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium-exchanging atpase activity
Specific Function
Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
Gene Name
ATP4A
Uniprot ID
P20648
Uniprot Name
Potassium-transporting ATPase alpha chain 1
Molecular Weight
114117.74 Da
References
  1. Moreira Dias L: Pantoprazole: a proton pump inhibitor. Clin Drug Investig. 2009;29 Suppl 2:3-12. doi: 10.2165/1153121-S0-000000000-00000. [Article]
  2. Cheer SM, Prakash A, Faulds D, Lamb HM: Pantoprazole: an update of its pharmacological properties and therapeutic use in the management of acid-related disorders. Drugs. 2003;63(1):101-33. [Article]
  3. Bardou M, Martin J: Pantoprazole: from drug metabolism to clinical relevance. Expert Opin Drug Metab Toxicol. 2008 Apr;4(4):471-83. doi: 10.1517/17425255.4.4.471 . [Article]
  4. Protonix delayed release and oral suspension FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name
DDAH1
Uniprot ID
O94760
Uniprot Name
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
Molecular Weight
31121.5 Da
References
  1. Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [Article]
  2. Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Ogilvie BW, Yerino P, Kazmi F, Buckley DB, Rostami-Hodjegan A, Paris BL, Toren P, Parkinson A: The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: implications for coadministration with clopidogrel. Drug Metab Dispos. 2011 Nov;39(11):2020-33. doi: 10.1124/dmd.111.041293. Epub 2011 Jul 27. [Article]
  2. Meyer UA: Interaction of proton pump inhibitors with cytochromes P450: consequences for drug interactions. Yale J Biol Med. 1996 May-Jun;69(3):203-9. [Article]
  3. Li W, Zeng S, Yu LS, Zhou Q: Pharmacokinetic drug interaction profile of omeprazole with adverse consequences and clinical risk management. Ther Clin Risk Manag. 2013;9:259-71. doi: 10.2147/TCRM.S43151. Epub 2013 May 27. [Article]
  4. El Rouby N, Lima JJ, Johnson JA: Proton pump inhibitors: from CYP2C19 pharmacogenetics to precision medicine. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):447-460. doi: 10.1080/17425255.2018.1461835. Epub 2018 Apr 12. [Article]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Meyer UA: Interaction of proton pump inhibitors with cytochromes P450: consequences for drug interactions. Yale J Biol Med. 1996 May-Jun;69(3):203-9. [Article]
  2. Protonix delayed release and oral suspension FDA label [File]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [Article]
  2. Wedemeyer RS, Blume H: Pharmacokinetic drug interaction profiles of proton pump inhibitors: an update. Drug Saf. 2014 Apr;37(4):201-11. doi: 10.1007/s40264-014-0144-0. [Article]
  3. Oostendorp RL, Buckle T, Beijnen JH, van Tellingen O, Schellens JH: The effect of P-gp (Mdr1a/1b), BCRP (Bcrp1) and P-gp/BCRP inhibitors on the in vivo absorption, distribution, metabolism and excretion of imatinib. Invest New Drugs. 2009 Feb;27(1):31-40. doi: 10.1007/s10637-008-9138-z. Epub 2008 May 1. [Article]
  4. Kunimatsu S, Mizuno T, Fukudo M, Katsura T: Effect of P-glycoprotein and breast cancer resistance protein inhibition on the pharmacokinetics of sunitinib in rats. Drug Metab Dispos. 2013 Aug;41(8):1592-7. doi: 10.1124/dmd.112.050286. Epub 2013 Jun 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Breedveld P, Zelcer N, Pluim D, Sonmezer O, Tibben MM, Beijnen JH, Schinkel AH, van Tellingen O, Borst P, Schellens JH: Mechanism of the pharmacokinetic interaction between methotrexate and benzimidazoles: potential role for breast cancer resistance protein in clinical drug-drug interactions. Cancer Res. 2004 Aug 15;64(16):5804-11. [Article]
  2. Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [Article]
  3. Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Oostendorp RL, van de Steeg E, van der Kruijssen CM, Beijnen JH, Kenworthy KE, Schinkel AH, Schellens JH: Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug Metab Dispos. 2009 Apr;37(4):917-23. doi: 10.1124/dmd.108.024901. Epub 2009 Jan 12. [Article]
  2. Chioukh R, Noel-Hudson MS, Ribes S, Fournier N, Becquemont L, Verstuyft C: Proton pump inhibitors inhibit methotrexate transport by renal basolateral organic anion transporter hOAT3. Drug Metab Dispos. 2014 Dec;42(12):2041-8. doi: 10.1124/dmd.114.058529. Epub 2014 Sep 19. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48