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=CC=NC(C[S+]([O-])C2=NC3=C(N2)C=C(OC(F)F)C=C3)=C1OC
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)
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 Date9.7182718E11 |
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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 Date9.7182718E11 |
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 |
---|---|---|
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality. | 2001 |
|
Comparison of pantoprazole 20 mg to ranitidine 150 mg b.i.d. in the treatment of mild gastroesophageal reflux disease. | 2001 |
|
Pantoprazole and cyclosporine or tacrolimus. | 2001 Apr |
|
[H2 receptor antagonists and proton pump inhibitors: principles and rules of use]. | 2001 Apr 15 |
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Resolution of Menetrier's disease after Helicobacter pylori eradication therapy. | 2001 Aug 24 |
|
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats. | 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 |
|
Effects on 24-hour intragastric pH: a comparison of lansoprazole administered nasogastrically in apple juice and pantoprazole administered intravenously. | 2001 Jul |
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Predictors of failure of Helicobacter pylori eradication with the standard 'Maastricht triple therapy'. | 2001 Jul |
|
Ranitidine bismuth citrate-based triple therapies after failure of the standard 'Maastricht triple therapy': a promising alternative to the quadruple therapy? | 2001 Jul |
|
Persistent eradication of Helicobacter pylori after systemic politherapy associated with periodontal pockets treatment with metronidazole and calcium sulphate. | 2001 Jul-Aug |
|
Pantoprazole therapy in the long-term management of severe acid peptic disease: clinical efficacy, safety, serum gastrin, gastric histology, and endocrine cell studies. | 2001 Jun |
|
[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 |
|
Pantoprazole. | 2001 Jun 1 |
|
Functionally impaired, hypertrophic ECL cells accumulate vacuoles and lipofuscin bodies. An ultrastructural study of ECL cells isolated from hypergastrinemic rats. | 2001 Mar |
|
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice. | 2001 Mar 9 |
|
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents. | 2001 May |
|
Shortcomings of the first-generation proton pump inhibitors. | 2001 May |
|
Reversible pheripheral edema in female patients taking proton pump inhibitors for peptic acid diseases. | 2001 May |
|
Resolution of granulomatous rosacea after eradication of Helicobacter pylori with clarithromycin, metronidazole and pantoprazole. | 2001 Nov |
|
Symptom relief in gastroesophageal reflux disease: a randomized, controlled comparison of pantoprazole and nizatidine in a mixed patient population with erosive esophagitis or endoscopy-negative reflux disease. | 2001 Oct |
|
Clinical significance of the cytochrome P450 2C19 genetic polymorphism. | 2002 |
|
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 |
|
Selective colonization by Helicobacter pylori of the deep gastric glands and intracellular canaliculi of parietal cells in the setting of chronic proton pump inhibitor use. | 2002 Apr |
|
Dose-dependent control of intragastric pH by pantoprazole, 10, 20 or 40 mg, in healthy volunteers. | 2002 Apr |
|
Pantoprazole IV (Protonix IV). | 2002 Apr 29 |
|
Efficacy of quadruple therapy with pantoprazole, bismuth, tetracycline and metronidazole as rescue treatment for Helicobacter pylori infection. | 2002 Aug |
|
[Proton pump inhibitors: Pantoprazole]. | 2002 Feb |
|
Nonallergic anaphylaxis to pantoprazole. | 2002 Feb |
|
Protonix. First i.v. proton pump inhibitor approved. | 2002 Feb |
|
Conformational analysis: a new approach by means of chemometrics. | 2002 Jan 30 |
|
Gateways to clinical trials. | 2002 Jan-Feb |
|
Enantioselective disposition of lansoprazole in extensive and poor metabolizers of CYP2C19. | 2002 Jul |
|
Are proton pump inhibitors the first choice for acute treatment of gastric ulcers? A meta analysis of randomized clinical trials. | 2002 Jul 15 |
|
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 |
|
Intravenous proton pump inhibitors in the critical care setting. | 2002 Jun |
|
Pharmacology of acid suppression in the hospital setting: focus on proton pump inhibition. | 2002 Jun |
|
[Correlation of Barrett's esophagus and colonic adenomas]. | 2002 Jun 9 |
|
[Intravenous 3-day Helicobacter pylori eradication therapy is highly effective in patients with bleeding peptic ulcer]. | 2002 Jun-Jul |
|
Proton pump activation in stimulated parietal cells is regulated by gastric acid secretory capacity: a human study. | 2002 May |
|
Combination drug therapy for gastroesophageal reflux disease. | 2002 May |
|
Randomised controlled trial of pantoprazole versus ranitidine for the treatment of uninvestigated heartburn in primary care. | 2002 Oct 21 |
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.
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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
Created by
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PRIMARY | |||
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4679
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PRIMARY | |||
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7292
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PRIMARY | |||
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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 |
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD