Details
Stereochemistry | MIXED |
Molecular Formula | 4C16H14F2N3O4S.2Mg.5H2O |
Molecular Weight | 1668.134 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.[Mg++].[Mg++].COC1=CC=NC(C[S+]([O-])C2=NC3=CC(OC(F)F)=CC=C3[N-]2)=C1OC.COC4=CC=NC(C[S+]([O-])C5=NC6=CC(OC(F)F)=CC=C6[N-]5)=C4OC.COC7=CC=NC(C[S+]([O-])C8=NC9=CC(OC(F)F)=CC=C9[N-]8)=C7OC.COC%10=CC=NC(C[S+]([O-])C%11=NC%12=CC(OC(F)F)=CC=C%12[N-]%11)=C%10OC
InChI
InChIKey=UKKGINHPEZBIFY-UHFFFAOYSA-N
InChI=1S/4C16H14F2N3O4S.2Mg.5H2O/c4*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;;;;;;;/h4*3-7,15H,8H2,1-2H3;;;5*1H2/q4*-1;2*+2;;;;;
Molecular Formula | C16H14F2N3O4S |
Molecular Weight | 382.362 |
Charge | -1 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Mg |
Molecular Weight | 24.305 |
Charge | 2 |
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 |
|||
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 |
|
Lansoprazole: an update of its place in the management of acid-related disorders. | 2001 |
|
Comparison of pantoprazole 20 mg to ranitidine 150 mg b.i.d. in the treatment of mild gastroesophageal reflux disease. | 2001 |
|
No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease. | 2001 Aug |
|
Resolution of Menetrier's disease after Helicobacter pylori eradication therapy. | 2001 Aug 24 |
|
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 |
|
Amoxycillin, clarithromycin and either sucralfate or pantoprazole for eradication of Helicobacter pylori in duodenal ulcer (a randomized controlled trial). | 2001 Dec 17 |
|
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats. | 2001 Feb |
|
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies. | 2001 Jan |
|
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 |
|
[Efficacy and safety of intravenously administered pantoprazole in the treatment of gastrinoma]. | 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 |
|
Pharmacological and pharmacodynamic essentials of H(2)-receptor antagonists and proton pump inhibitors for the practising physician. | 2001 Jun |
|
Proton pump inhibitors: a study of GPs' prescribing. | 2001 Jun |
|
Pantoprazole. | 2001 Jun 1 |
|
Proton pump inhibitors and their drug interactions: an evidence-based approach. | 2001 May |
|
Cluster headache without autonomic symptoms? | 2001 Nov |
|
Resolution of granulomatous rosacea after eradication of Helicobacter pylori with clarithromycin, metronidazole and pantoprazole. | 2001 Nov |
|
Efficacy of medical therapy and antireflux surgery to prevent Barrett's metaplasia in patients with gastroesophageal reflux disease. | 2001 Nov |
|
Systematic review of proton pump inhibitors for the acute treatment of reflux oesophagitis. | 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 |
|
[Microflora of gastric juice in patients after eradication of Helicobacter pylori and treatment with a proton pump inhibitor]. | 2002 |
|
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 |
|
Nonallergic anaphylaxis to pantoprazole. | 2002 Feb |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Factors associated with treatment failure of Helicobacter pylori infection in a developing country. | 2002 Oct |
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
Sat Dec 16 19:22:03 GMT 2023
by
admin
on
Sat Dec 16 19:22:03 GMT 2023
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Record UNII |
PHN3JS5S59
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Record Status |
Validated (UNII)
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Record Version |
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-
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Systematic Name | English |
Code System | Code | Type | Description | ||
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166177259
Created by
admin on Sat Dec 16 19:22:03 GMT 2023 , Edited by admin on Sat Dec 16 19:22:03 GMT 2023
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PHN3JS5S59
Created by
admin on Sat Dec 16 19:22:03 GMT 2023 , Edited by admin on Sat Dec 16 19:22:03 GMT 2023
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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