Identification

Name
Pantoprazole
Accession Number
DB00213  (APRD00073)
Type
Small Molecule
Groups
Approved
Description

Pantoprazole is a proton pump inhibitor drug used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease.

Structure
Thumb
Synonyms
  • Pantoprazol
  • Pantoprazolum
Product Ingredients
IngredientUNIICASInChI Key
Pantoprazole magnesium1AL13B11R4199387-73-0RDRUTBCDIVCMMX-UHFFFAOYSA-N
Pantoprazole magnesium hemipentahydrateNot AvailableNot AvailableNot applicable
Pantoprazole sodiumS9363155XL138786-67-1YNWDKZIIWCEDEE-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act PantoprazoleTablet, delayed release40 mgOralActavis Pharma Company2008-06-04Not applicableCanada
Controloc ControlTablet, delayed release20 mgOralTakeda2009-06-12Not applicableEu
Controloc ControlTablet, delayed release20 mgOralTakeda2009-06-12Not applicableEu
Controloc ControlTablet, delayed release20 mgOralTakeda2009-06-12Not applicableEu
Controloc ControlTablet, delayed release20 mgOralTakeda2009-06-12Not applicableEu
M-pantoprazoleTablet, delayed release40 mgOralMantra Pharma Inc2017-11-01Not applicableCanada
Panto IVPowder, for solution40 mgIntravenousTakeda1999-04-062017-02-27Canada
Panto-bykTablet, delayed release20 mgOralNycomedNot applicableNot applicableCanada
Panto-bykTablet, delayed release40 mgOralNycomedNot applicableNot applicableCanada
PantolocTablet, delayed release40 mgOralTakeda1997-03-05Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-pantoprazoleTablet, delayed release40 mgOralAbbott2014-03-172015-12-31Canada
Abbott-pantoprazoleTablet, delayed release20 mgOralAbbottNot applicableNot applicableCanada
Apo-pantoprazoleTablet, delayed release20 mgOralApotex Corporation2008-03-05Not applicableCanada
Apo-pantoprazoleTablet, delayed release40 mgOralApotex Corporation2008-03-05Not applicableCanada
Auro-pantoprazoleTablet, delayed release40 mgOralAuro Pharma Inc2016-02-06Not applicableCanada
Ava-pantoprazoleTablet, delayed release40 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-pantoprazoleTablet, delayed release20 mgOralAvanstra Inc2011-09-192014-08-21Canada
Bio-pantoprazoleTablet, delayed release40 mgOralBiomed Pharma2016-11-24Not applicableCanada
Dom-pantoprazoleTablet, delayed release20 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-pantoprazoleTablet, delayed release40 mgOralDominion Pharmacal2012-10-25Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Pantecta ControlPantoprazole (20 mg)Tablet, delayed releaseOralTakeda2009-06-122016-11-15Eu
Pantecta ControlPantoprazole (20 mg)Tablet, delayed releaseOralTakeda2009-06-122016-11-15Eu
Pantecta ControlPantoprazole (20 mg)Tablet, delayed releaseOralTakeda2009-06-122016-11-15Eu
Pantecta ControlPantoprazole (20 mg)Tablet, delayed releaseOralTakeda2009-06-122016-11-15Eu
International/Other Brands
Pantozol
Categories
UNII
D8TST4O562
CAS number
102625-70-7
Weight
Average: 383.37
Monoisotopic: 383.075133083
Chemical Formula
C16H15F2N3O4S
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

Pharmacology

Indication

Short-term (up to 16 weeks) treatment of erosive esophagitis.

Associated Conditions
Pharmacodynamics

Pantoprazole is a substituted benzimidazole indicated for the short-term treatment (up to 16 weeks) in the healing and symptomatic relief of erosive esophagitis. Pantoprazole is a proton pump inhibitor (PPI) that suppresses the final step in gastric acid production.

Mechanism of action

Pantoprazole is a proton pump inhibitor (PPI) that suppresses the final step in gastric acid production by forming a covalent bond to two sites of the (H+,K+ )- ATPase enzyme system at the secretory surface of the gastric parietal cell. This effect is dose- related and leads to inhibition of both basal and stimulated gastric acid secretion irrespective of the stimulus.

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Human
Absorption

Pantoprazole is well absorbed. It undergoes little first-pass metabolism resulting in an absolute bioavailability of approximately 77%.

Volume of distribution
  • 11.0 to 23.6 L
Protein binding

98%

Metabolism

Pantoprazole is extensively metabolized in the liver through the cytochrome P450 (CYP) system. The main metabolic pathway is demethylation, by CYP2C19, with subsequent sulfation; other metabolic pathways include oxidation by CYP3A4. There is no evidence that any of the pantoprazole metabolites have significant pharmacologic activity.

Route of elimination

After administration of a single intravenous dose of 14C-labeled pantoprazole to healthy, normal metabolizer subjects, approximately 71% of the dose was excreted in the urine with 18% excreted in the feces through biliary excretion.

Half life

1 hour

Clearance
  • 7.6-14.0 L/h
Toxicity

Single intravenous doses of pantoprazole at 378, 230, and 266 mg/kg (38, 46, and 177 times the recommended human dose based on body surface area) were lethal to mice, rats and dogs, respectively. The symptoms of toxicity included hypoactivity, ataxia, hunched sitting, limb-splay, lateral position, segregation, absence of ear reflex, and tremor. There is limited experience regarding cases of human overdosage, and treatment should be symptomatic and supportive.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Pantoprazole Action PathwayDrug action
Pantoprazole Metabolism PathwayDrug metabolism
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Pantoprazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Pantoprazole.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be increased when combined with Pantoprazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Pantoprazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Pantoprazole.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Pantoprazole.
6-Deoxyerythronolide BThe metabolism of Pantoprazole can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Pantoprazole.
AbacavirPantoprazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibPantoprazole may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

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

US20030003058
General References
Not Available
External Links
Human Metabolome Database
HMDB0005017
KEGG Drug
D05353
KEGG Compound
C11806
PubChem Compound
4679
PubChem Substance
46504622
ChemSpider
4517
BindingDB
50241342
ChEBI
7915
ChEMBL
CHEMBL1502
Therapeutic Targets Database
DAP000724
PharmGKB
PA450774
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pantoprazole
ATC Codes
A02BC02 — PantoprazoleA02BD04 — Pantoprazole, amoxicillin and clarithromycinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazole
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (183 KB)
MSDS
Download (58.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableDrug Interactions1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceBacterial Infections1
1CompletedBasic ScienceDrug Interaction Potentiation1
1CompletedBasic ScienceDrug Interactions / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceGastroesophageal Reflux Disease1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedTreatmentAcute Coronary Syndromes (ACS)1
1CompletedTreatmentAdvanced Solid Tumours1
1CompletedTreatmentDisseminated Sclerosis1
1CompletedTreatmentFasting1
1CompletedTreatmentFed1
1CompletedTreatmentHealthy Volunteers12
1CompletedTreatmentReflux, Gastroesophageal1
1Not Yet RecruitingTreatmentMetastatic Colorectal Cancers1
1Unknown StatusBasic ScienceBMI >30 kg/m2 / Gastro-esophageal Reflux Disease (GERD)1
1Unknown StatusTreatmentHealthy Male Subjects1
1WithdrawnTreatmentInvasive Aspergillosis1
1, 2RecruitingTreatmentMalignant Neoplasm of Pancreas1
2Active Not RecruitingSupportive CareNephrotoxicity / Ototoxicity / Sarcoma, Osteogenic1
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedPreventionPeptic ulcer haemorrhage1
2CompletedTreatmentCerebrovascular Accident, Acute / Edema of the cerebrum1
2CompletedTreatmentDiabetes, Diabetes Mellitus Type 11
2CompletedTreatmentGastrinoma / Zollinger-Ellison Syndrome1
2Not Yet RecruitingTreatmentMetastatic Colorectal Cancers1
2, 3CompletedTreatmentGastroesophageal Reflux Disease1
2, 3CompletedTreatmentType 2 Diabetes Mellitus1
2, 3RecruitingTreatmentAcute Exacerbation of Psychosis / Psychosis / Schizophrenic Disorders1
3Active Not RecruitingPreventionPrevention & Control1
3CompletedPreventionPeptic ulcer haemorrhage1
3CompletedPreventionStress Ulcer Prophylaxis1
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Peptic Ulcers1
3CompletedTreatmentPeptic Ulcers1
3CompletedTreatmentPeptic Ulcers / Upper Gastrointestinal Hemorrhage1
3CompletedTreatmentReflux, Gastroesophageal6
3Not Yet RecruitingPreventionGastrointestinal Hemorrhage (Clinically Important, Upper)1
3RecruitingTreatmentAcute and Chronic Inflammation / Indigestion1
3RecruitingTreatmentHemorrhage, Gastrointestinal1
3RecruitingTreatmentLaryngopharyngeal Reflux Disease1
3TerminatedTreatmentEsophageal Metaplasia1
3Unknown StatusTreatmentChronic Use of Acid Suppressive Medication / Gastro-esophageal Reflux Disease (GERD) / GORD / Peptic Ulcers / Reflux1
3Unknown StatusTreatmentDiabetes Mellitus (DM)1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3Unknown StatusTreatmentPeptic Ulcers1
3WithdrawnTreatmentCongestive Heart Failure (CHF)1
3WithdrawnTreatmentGastric pH Control1
3WithdrawnTreatmentGastroesophageal Reflux Disease1
4Active Not RecruitingOtherPsychotic Disorder NOS / Reflux, Gastroesophageal1
4CompletedNot AvailableHealthy Volunteers1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedOtherAcute Kidney Injury (AKI) / Critical Illness / End-Stage Renal Disease (ESRD) / Proton Pump Inhibitor / Renal Replacement Therapies1
4CompletedPreventionGastrointestinal Bleedings / Stress Ulcers1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedPreventionPeptic Ulcer/Erosions1
4CompletedPreventionPeptic ulcer haemorrhage1
4CompletedTreatmentAcid Reflux Disease / Obstructive Sleep Apnea (OSA)1
4CompletedTreatmentAcid Regurgitation / Heartburn / Nausea / Upper Abdominal Pain1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4CompletedTreatmentBioavailability / Concomitant Medication After Renal Transplantation / Drug Interactions / Immunosuppressive Medication After Renal Transplantation1
4CompletedTreatmentEmergency / Indigestion / Pain1
4CompletedTreatmentEsophagitis1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / GORD / Reflux, Gastroesophageal1
4CompletedTreatmentGastroesophageal Reflux Disease3
4CompletedTreatmentHaemorrhage / Varices, Esophageal1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentIndigestion1
4CompletedTreatmentPeptic ulcer haemorrhage1
4CompletedTreatmentReflux, Gastroesophageal2
4CompletedTreatmentVasoconstrictor Choice on Acute Variceal Bleeding1
4Not Yet RecruitingPreventionGastric Ulcer Induced by Antiplatelet Agent / Proton Pump Inhibitor / Ulcer of the Gastrointestinal Tract1
4Not Yet RecruitingTreatmentPostoperative pain1
4RecruitingTreatmentDysbiosis1
4RecruitingTreatmentGastroesophageal Reflux Disease / Presumptive or Proven Gastroesophageal Reflux Disease (GERD)1
4RecruitingTreatmentNSAID-induced Gastropathy1
4RecruitingTreatmentRib Fractures / Wounds and Injuries1
4TerminatedTreatmentFunctional Dyspepsia1
4TerminatedTreatmentGastroesophageal Reflux Disease / Non-erosive Reflux Disease (NERD)1
4Unknown StatusPreventionAcute Coronary Syndromes (ACS)1
4Unknown StatusScreening30 Healthy People1
4Unknown StatusTreatmentCoronary Artery Disease1
4Unknown StatusTreatmentEsophageal Variceal Rebleeding1
4Unknown StatusTreatmentNonulcer Dyspepsia1
4WithdrawnTreatmentCoronary Artery Disease1
4WithdrawnTreatmentCoronary artery thrombosis / Positive Helicobacter Pylori Serology / Supra-aortic Artery Thrombosis1
4WithdrawnTreatmentEustachian Tube Dysfunction / Laryngopharyngeal Reflux1
4WithdrawnTreatmentPeptic Ulcers1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableErosive Gastroesophageal Reflux Disease / Non-erosive Reflux Disease (NERD)1
Not AvailableCompletedNot AvailableGastroesophageal Reflux Disease2
Not AvailableCompletedNot AvailableGastroesophageal Reflux Disease / Non-erosive Reflux Disease (NERD) / Sleep disorders and disturbances1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableHelicobacter Infections1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedSupportive CareAntiplatelet Effect1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Cerebrovascular Disorders1
Not AvailableCompletedTreatmentGastric Ulcer (GU)1
Not AvailableCompletedTreatmentGastrointestinal Diseases / Indigestion1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)2
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableRecruitingDiagnosticNon-erosive Reflux Disease (NERD) / Reflux, Gastroesophageal1
Not AvailableRecruitingPreventionPeptic Ulcers1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableRecruitingTreatmentElbow Trauma Requiring Operative Management1
Not AvailableTerminatedTreatmentNeoplasms Metastasis / Spinal Cord Compression1
Not AvailableTerminatedTreatmentUpper Gastrointestinal Bleed1
Not AvailableUnknown StatusPreventionDelayed Bleeding1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableUnknown StatusTreatmentEndoscopy / Haemorrhage / Peptic Ulcers / Proton Pump Inhibitors1
Not AvailableUnknown StatusTreatmentHemochromatosis1

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
Tablet, delayed releaseOral20 mg
Tablet, delayed releaseOral40 mg
Injection, powder, for solutionIntravenous40 mg/1
Injection, powder, lyophilized, for solutionIntravenous40 mg/1
TabletOral40 mg/1
Tablet, delayed releaseOral20 mg/1
Tablet, delayed releaseOral40 mg/1
Powder, for solutionIntravenous40 mg
Granule, delayed releaseOral40 mg/1
Injection, powder, for solutionIntravenous40 mg/10mL
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)
US4758579No1993-07-192010-07-19Us
CA2428870No2006-05-232021-11-17Canada
CA2092694No2005-04-052011-09-06Canada
CA2341031No2006-04-042019-08-12Canada
US5997903Yes1997-06-072017-06-07Us
US8754108Yes2002-05-172022-05-17Us
US6780881Yes2002-05-172022-05-17Us
US7351723Yes2002-05-172022-05-17Us
US7550153Yes2005-03-302025-03-30Us
US7553498Yes2005-03-302025-03-30Us
US7838027Yes2005-03-302025-03-30Us
US7544370Yes2006-12-072026-12-07Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)Because of gradual degradation of pantoprazole sodium during heating, the melting point cannot be determined.Not Available
water solubilityFreely soluble in water.Not Available
logP0.5Not Available
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-MSNot Available
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
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

Taxonomy

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
Sulfinylbenzimidazole / Alkyl aryl ether / Pyridine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Sulfoxide / Azacycle / Sulfinyl compound
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, aromatic ether, sulfoxide, pyridines, benzimidazoles (CHEBI:7915)

Targets

Kind
Protein
Organism
Human
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. [PubMed:19938880]
  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. [PubMed:12487624]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:21795468]
  3. 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. [PubMed:9165689]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. [PubMed:11770010]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. [PubMed:15313923]
  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. [PubMed:19076159]
  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. [PubMed:19541926]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 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. [PubMed:19139163]

Drug created on June 13, 2005 07:24 / Updated on September 22, 2018 22:42