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
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 |
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 |
|||
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 |
|||
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 |
|
No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease. | 2001 Aug |
|
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 |
|
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 |
|
Bioavailability of a crushed pantoprazole tablet after buffering with sodium hydrogencarbonate or magaldrate relative to the intact enteric coated pantoprazole tablet. | 2001 Jan-Feb |
|
Relapse prevention in reflux oesophagitis with regard to Helicobacter pylori status: a double-blind, randomized, multicentre trial to compare the efficacy of pantoprazole versus ranitidine. | 2001 Jul |
|
Cure of Helicobacter pylori infection in elderly patients: comparison of low versus high doses of clarithromycin in combination with amoxicillin and pantoprazole. | 2001 Jul |
|
Persistent eradication of Helicobacter pylori after systemic politherapy associated with periodontal pockets treatment with metronidazole and calcium sulphate. | 2001 Jul-Aug |
|
[Efficacy and safety of intravenously administered pantoprazole in the treatment of gastrinoma]. | 2001 Jul-Aug |
|
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 |
|
Reversible pheripheral edema in female patients taking proton pump inhibitors for peptic acid diseases. | 2001 May |
|
Effect of aggressive therapy on laryngeal symptoms and voice characteristics in patients with gastroesophageal reflux. | 2001 Oct |
|
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 |
|
[Submicroscopic aspects of the mechanism of inhibitors of H+/K+-ATPase in gastric parietal cells]. | 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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Acid suppression in healthy subjects following lansoprazole or pantoprazole. | 2002 Mar |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:58:22 GMT 2023
by
admin
on
Fri Dec 15 17:58:22 GMT 2023
|
Record UNII |
1AL13B11R4
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
1AL13B11R4
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY | |||
|
SUB22265
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY | |||
|
DBSALT000853
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY | |||
|
199387-73-0
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY | |||
|
71587624
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY | |||
|
100000085425
Created by
admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SOLVATE->ANHYDROUS |
|
||
|
SOLVATE->ANHYDROUS |
|
||
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|