Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H15F2N3O4S |
Molecular Weight | 383.37 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(C[S+]([O-])C2=NC3=C(N2)C=C(OC(F)F)C=C3)=NC=C1
InChI
InChIKey=IQPSEEYGBUAQFF-UHFFFAOYSA-N
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)
Molecular Formula | C16H15F2N3O4S |
Molecular Weight | 383.37 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11402494 | https://www.ncbi.nlm.nih.gov/pubmed/24301963
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11402494 | https://www.ncbi.nlm.nih.gov/pubmed/24301963
Pantoprazole is a proton pump inhibitor that inhibits gastric acid secretion and used for short-term treatment of erosive esophagitis associated with gastroesophageal reflux disease. Pantoprazole suppresses the final step in gastric acid production by covalently binding to the (H+, K+)-ATPase enzyme system at the secretory surface of the gastric parietal cell. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. The binding to the (H+, K+)-ATPase results in a duration of antisecretory effect that persists longer than 24 hours. Pantoprazole is used for short-term treatment of erosion and ulceration of the esophagus for adults and pediatric patients 5 years of age and older caused by gastroesophageal reflux disease. It can be used as a maintenance therapy for long-term use after initial response is obtained, but there have not been any controlled studies about the use of pantoprazole past a duration of 12 months. Pantoprazole may also be used in combination with antibiotics to treat ulcers caused by Helicobacter pylori. Use of pantoprazole may increase the chance of developing infections such as pneumonia, particularly in hospitalized patients.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11402494
Curator's Comment: # Wyeth-Ayerst Pharmaceuticals
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095173 |
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Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11402494 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PROTONIX Approved UseINDICATIONS AND USAGE. PROTONIX is a proton pump inhibitor indicated for the following: Short-Term Treatment of Erosive Esophagitis Associated with Gastroesophageal Reflux Disease (GERD). Maintenance of Healing of Erosive Esophagitis. Pathological Hypersecretory Conditions Including ZollingerEllison Syndrome. Launch Date2000 |
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Primary | PROTONIX Approved UseINDICATIONS AND USAGE. PROTONIX is a proton pump inhibitor indicated for the following: Short-Term Treatment of Erosive Esophagitis Associated with Gastroesophageal Reflux Disease (GERD). Maintenance of Healing of Erosive Esophagitis. Pathological Hypersecretory Conditions Including ZollingerEllison Syndrome. Launch Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.4 μg/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PANTOPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.8 μg × h/mL |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PANTOPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1 h |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
PANTOPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [Activation 22.3872 uM] | ||||
likely | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >500 uM] | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 93 uM] | ||||
yes [IC50 17.9 uM] | ||||
yes [IC50 2.8 uM] | ||||
yes [IC50 22.9 uM] | ||||
yes [IC50 30.8 uM] | ||||
yes [IC50 4.45 uM] | ||||
yes [IC50 43.2 uM] | ||||
yes [IC50 5.5 uM] | ||||
yes [IC50 63.21 uM] | ||||
yes [Ki 6.5 uM] | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20987_Protonix_pharmr_P7.pdf#page=21 Page: (Pharm_P7) 21 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20987_Protonix_pharmr_P7.pdf#page=22 Page: (Pharm_P7) 22 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20987_Protonix_pharmr_P7.pdf#page=22 Page: (Pharm_P7) 22 |
yes | |||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (Pharm_P7) 22, (ClinP_P1) 25 |
major | |||
Page: (Pharm_P7) 22, (ClinP_P1) 25 |
major | |||
Page: (Pharm_P7) 22, (ClinP_P1) 25 |
minor | |||
Page: (Pharm_P7) 22, (ClinP_P1) 25 |
minor | |||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies. | 2000 Oct |
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Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study. | 2001 |
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Pantoprazole and cyclosporine or tacrolimus. | 2001 Apr |
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No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease. | 2001 Aug |
|
Oral pantoprazole for acid suppression in the treatment of patients with Zollinger-Ellison syndrome. | 2001 Dec |
|
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy. | 2001 Feb |
|
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study. | 2001 Feb |
|
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies. | 2001 Jan |
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Switching between intravenous and oral pantoprazole. | 2001 Jan |
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Bioavailability of a crushed pantoprazole tablet after buffering with sodium hydrogencarbonate or magaldrate relative to the intact enteric coated pantoprazole tablet. | 2001 Jan-Feb |
|
Ranitidine bismuth citrate-based triple therapies after failure of the standard 'Maastricht triple therapy': a promising alternative to the quadruple therapy? | 2001 Jul |
|
[Role of Helicobacter pylori infection in insulin-dependent diabetes mellitus]. | 2001 Jun |
|
Fish oil (Eicosapen) is less effective than metronidazole, in combination with pantoprazole and clarithromycin, for Helicobacter pylori eradication. | 2001 Jun |
|
Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes. | 2001 Jun |
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Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin. | 2001 Mar |
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Is there any relationship between functional dyspepsia and chronic gastritis associated with Helicobacter pylori infection? | 2001 Mar-Apr |
|
Cluster headache without autonomic symptoms? | 2001 Nov |
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A comparison of simplified lansoprazole suspension administered nasogastrically and pantoprazole administered intravenously: effects on 24-h intragastric pH. | 2001 Nov |
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Efficacy and tolerability of pantoprazole versus ranitidine in the treatment of reflux esophagitis and the influence of Helicobacter pylori infection on healing rate. | 2002 |
|
[Microflora of gastric juice in patients after eradication of Helicobacter pylori and treatment with a proton pump inhibitor]. | 2002 |
|
Protonix. First i.v. proton pump inhibitor approved. | 2002 Feb |
|
Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography. | 2002 Jan 5 |
|
Are proton pump inhibitors the first choice for acute treatment of gastric ulcers? A meta analysis of randomized clinical trials. | 2002 Jul 15 |
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Efficacy and tolerability of ranitidine bismuth citrate plus amoxycillin and clarithromycin as first- or second-line therapy to cure Helicobacter pylori infection. | 2002 Jul-Aug |
|
Long-term clinical outcome of elderly patients with reflux esophagitis: a six-month to three-year follow-up study. | 2002 Jul-Aug |
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Pantoprazole-induced recurrent anaphylactic shock. | 2002 Jun |
|
Intravenous proton pump inhibitors in the critical care setting. | 2002 Jun |
|
Stress-related mucosal disease in the critically ill patient: risk factors and strategies to prevent stress-related bleeding in the intensive care unit. | 2002 Jun |
|
A double-blind, randomized comparison of omeprazole Multiple Unit Pellet System (MUPS) 20 mg, lansoprazole 30 mg and pantoprazole 40 mg in symptomatic reflux oesophagitis followed by 3 months of omeprazole MUPS maintenance treatment: a Dutch multicentre trial. | 2002 Jun |
|
Single vs. double dose of a proton pump inhibitor in triple therapy for Helicobacter pylori eradication: a meta-analysis. | 2002 Jun |
|
[Correlation of Barrett's esophagus and colonic adenomas]. | 2002 Jun 9 |
|
Proton pump activation in stimulated parietal cells is regulated by gastric acid secretory capacity: a human study. | 2002 May |
|
Stability of pantoprazole in an extemporaneously compounded oral liquid. | 2002 May 15 |
Sample Use Guides
Oral use: Short-Term Treatment of Erosive Esophagitis Associated With GERD: 40 mg Once daily for up to 8 weeks; Pathological Hypersecretory Conditions Including Zollinger-Ellison Syndrome: 40 mg Twice daily
IV: The recommended adult dose is 40 mg pantoprazole given once daily by intravenous infusion for 7 to 10 days
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24301963
To determine "ex vivo" gastric mucosa gastric acid secretion, pantoprazole (as DMSO solution diluted with serosal fluid) was added to membrane mucosa liquid in the bath tube. Pantoprazole final concentration in serosal fluidwas 5 mkM, incubation time -- 2.5h. Pantoprazole mediated gastric acid secretion inhibition is 24.3% at 5mkM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:07:32 GMT 2025
by
admin
on
Mon Mar 31 18:07:32 GMT 2025
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Record UNII |
D8TST4O562
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175525
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WHO-VATC |
QA02BD04
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WHO-VATC |
QA02BC02
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NDF-RT |
N0000000147
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EMA ASSESSMENT REPORTS |
SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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NCI_THESAURUS |
C29723
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WHO-ATC |
A02BD04
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EMA ASSESSMENT REPORTS |
PANTOLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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WHO-ATC |
A02BD11
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WHO-ATC |
A02BC02
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EMA ASSESSMENT REPORTS |
CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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EMA ASSESSMENT REPORTS |
PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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EMA ASSESSMENT REPORTS |
PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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LIVERTOX |
NBK548461
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Code System | Code | Type | Description | ||
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PANTOPRAZOLE
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4679
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7292
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DB00213
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40790
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PRIMARY | RxNorm | ||
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Pantoprazole
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102625-70-7
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759257
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DTXSID4023416
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7260
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SUB09608MIG
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7915
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2054
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m8387
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D8TST4O562
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C064276
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C29346
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6548
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CHEMBL1502
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100000092491
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D8TST4O562
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DD-26
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154644-14-1
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SUPERSEDED |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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