Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C16H14F2N3O4S.Mg |
Molecular Weight | 789.029 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].COC1=CC=NC(C[S+]([O-])C2=NC3=C([N-]2)C=C(OC(F)F)C=C3)=C1OC.COC4=CC=NC(C[S+]([O-])C5=NC6=C([N-]5)C=C(OC(F)F)C=C6)=C4OC
InChI
InChIKey=RDRUTBCDIVCMMX-UHFFFAOYSA-N
InChI=1S/2C16H14F2N3O4S.Mg/c2*1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16;/h2*3-7,15H,8H2,1-2H3;/q2*-1;+2
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 |
|||
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 |
---|---|---|
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality. | 2001 |
|
Prophylaxis and treatment of non-steroidal anti-inflammatory drug-induced upper gastrointestinal side-effects. | 2001 Dec |
|
Proton pump inhibitors and gastric acid secretion. | 2001 Dec |
|
Replacement of oral proton pump inhibitors with intravenous pantoprazole to effectively control gastric acid hypersecretion in patients with Zollinger-Ellison syndrome. | 2001 Dec |
|
Oral pantoprazole for acid suppression in the treatment of patients with Zollinger-Ellison syndrome. | 2001 Dec |
|
Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. | 2001 Dec |
|
Effect of inhibition of gastric acid secretion on antropyloroduodenal motor activity and duodenal acid hypersensitivity in functional dyspepsia. | 2001 Dec |
|
Amoxycillin, clarithromycin and either sucralfate or pantoprazole for eradication of Helicobacter pylori in duodenal ulcer (a randomized controlled trial). | 2001 Dec 17 |
|
Persistent eradication of Helicobacter pylori after systemic politherapy associated with periodontal pockets treatment with metronidazole and calcium sulphate. | 2001 Jul-Aug |
|
Cluster headache without autonomic symptoms? | 2001 Nov |
|
[Submicroscopic aspects of the mechanism of inhibitors of H+/K+-ATPase in gastric parietal cells]. | 2002 |
|
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 |
|
Effect of pantoprazole versus other proton pump inhibitors on 24-hour intragastric pH and basal acid output in Zollinger-Ellison syndrome. | 2002 Apr |
|
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 |
|
The novel use of an intravenous proton pump inhibitor in a patient with short bowel syndrome. | 2002 Jan |
|
Conformational analysis: a new approach by means of chemometrics. | 2002 Jan 30 |
|
Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography. | 2002 Jan 5 |
|
Gateways to clinical trials. | 2002 Jan-Feb |
|
Early relief of upper gastrointestinal dyspeptic symptoms: a survey of empirical therapy with pantoprazole in Canadian clinical practice. | 2002 Jul |
|
Enantioselective disposition of lansoprazole in extensive and poor metabolizers of CYP2C19. | 2002 Jul |
|
Proton pump inhibitors: an update. | 2002 Jul 15 |
|
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 |
|
Long-term clinical outcome of elderly patients with reflux esophagitis: a six-month to three-year follow-up study. | 2002 Jul-Aug |
|
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 |
|
Pharmacology of acid suppression in the hospital setting: focus on proton pump inhibition. | 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 |
|
Drug points: Severe myalgia from an interaction between treatments with pantoprazole and methotrexate. | 2002 Jun 22 |
|
[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 |
|
Different effects of short-term omeprazole, lansoprazole or pantoprazole on the accuracy of the (13)C-urea breath test. | 2002 Mar |
|
Acid suppression in healthy subjects following lansoprazole or pantoprazole. | 2002 Mar |
|
Review article: rabeprazole-based therapy in Helicobacter pylori eradication. | 2002 Mar |
|
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 |
|
Stability of pantoprazole in an extemporaneously compounded oral liquid. | 2002 May 15 |
|
Factors associated with treatment failure of Helicobacter pylori infection in a developing country. | 2002 Oct |
|
Randomised controlled trial of pantoprazole versus ranitidine for the treatment of uninvestigated heartburn in primary care. | 2002 Oct 21 |
|
Short-term therapeutic trial of proton pump inhibitors in suspected extraesophageal reflux. | 2002 Sep |
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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1AL13B11R4
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SUB22265
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DBSALT000853
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199387-73-0
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71587624
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100000085425
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD