U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H15F2N3O4S
Molecular Weight 383.3715
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE

SMILES

COc1ccnc(CS(=O)c2nc3ccc(cc3[nH]2)OC(F)F)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)

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment:: # Wyeth-Ayerst Pharmaceuticals

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROTONIX

Approved Use

INDICATIONS 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 Date

9.7182718E11
Primary
PROTONIX

Approved Use

INDICATIONS 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 Date

9.7182718E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
yes
yes
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
major
minor
minor
yes
yes
PubMed

PubMed

TitleDatePubMed
Lansoprazole: an update of its place in the management of acid-related disorders.
2001
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
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
Six regimens for the eradication of Helicobacter pylori (Hp) in duodenal ulcer patients: three consecutive trials (1995-1999).
2001 Jan-Dec
Bioavailability of a crushed pantoprazole tablet after buffering with sodium hydrogencarbonate or magaldrate relative to the intact enteric coated pantoprazole tablet.
2001 Jan-Feb
Healing and relapse rates in gastroesophageal reflux disease treated with the newer proton-pump inhibitors lansoprazole, rabeprazole, and pantoprazole compared with omeprazole, ranitidine, and placebo: evidence from randomized clinical trials.
2001 Jul
Possible phototoxicity with subsequent progression to discoid lupus following pantoprazole administration.
2001 Jul
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
Effects on 24-hour intragastric pH: a comparison of lansoprazole administered nasogastrically in apple juice and pantoprazole administered intravenously.
2001 Jul
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
[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
Is there any relationship between functional dyspepsia and chronic gastritis associated with Helicobacter pylori infection?
2001 Mar-Apr
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.
2001 May
Shortcomings of the first-generation proton pump inhibitors.
2001 May
Proton pump inhibitors and their drug interactions: an evidence-based approach.
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
Efficacy of medical therapy and antireflux surgery to prevent Barrett's metaplasia in patients with gastroesophageal reflux disease.
2001 Nov
A comparison of simplified lansoprazole suspension administered nasogastrically and pantoprazole administered intravenously: effects on 24-h intragastric pH.
2001 Nov
Systematic review of proton pump inhibitors for the acute treatment of reflux oesophagitis.
2001 Nov
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
Influence of pantoprazole on oesophageal motility, and bile and acid reflux in patients with oesophagitis.
2001 Sep
[Comparative study of proton pump inhibitors].
2001 Sep 9
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
Pantoprazole IV (Protonix IV).
2002 Apr 29
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
Enantioselective disposition of lansoprazole in extensive and poor metabolizers of CYP2C19.
2002 Jul
Proton pump inhibitors: an update.
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
Pantoprazole-induced recurrent anaphylactic shock.
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
[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
Randomised controlled trial of pantoprazole versus ranitidine for the treatment of uninvestigated heartburn in primary care.
2002 Oct 21
Patents

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
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.
Name Type Language
PANTOPRAZOLE
EMA EPAR   HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
PANTOPRAZOLE [HSDB]
Common Name English
5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDINYL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
Systematic Name English
ZOVANTA
Brand Name English
PANTOPRAZOLE [WHO-DD]
Common Name English
PANTOPRAZOLE [VANDF]
Common Name English
BY-1023
Code English
PANTOPRAZOLE [MART.]
Common Name English
PANTOZOL
Brand Name English
PANTOCID
Brand Name English
PANTOPRAZOLE [INN]
Common Name English
SK&F-96022
Code English
(+/-)-PANTOPRAZOLE
Common Name English
2-(((3,4-DIMETHOXYPYRIDIN-2-YL)METHYL)SULFINYL)-5-DIFLUOROMETHOXY-1H-BENZIMIDAZOLE
Systematic Name English
BY 1023
Code English
1H-BENZIMIDAZOLE, 5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDINYL)METHYL)SULFINYL)-
Systematic Name English
5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE
Systematic Name English
NSC-759257
Code English
ALTOPAN
Common Name English
PANTOPRAZOLE [MI]
Common Name English
PANTOPRAZOLE [EMA EPAR]
Common Name English
6-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDINYL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
Systematic Name English
PANTOLOC
Brand Name English
SKF-96022
Code English
PANTOPRAZOLE [USAN]
Common Name English
1H-BENZIMIDAZOLE, 5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDYL)METHYL)SULFINYL)-
Systematic Name English
SK&F 96022
Code English
Classification Tree Code System Code
NDF-RT N0000175525
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
WHO-VATC QA02BD04
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
WHO-VATC QA02BC02
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
NDF-RT N0000000147
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
EMA ASSESSMENT REPORTS SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
NCI_THESAURUS C29723
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
WHO-ATC A02BD04
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
EMA ASSESSMENT REPORTS PANTOLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
WHO-ATC A02BD11
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
WHO-ATC A02BC02
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
EMA ASSESSMENT REPORTS CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
EMA ASSESSMENT REPORTS PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
EMA ASSESSMENT REPORTS PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
LIVERTOX 737
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
Code System Code Type Description
WIKIPEDIA
PANTOPRAZOLE
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
PUBCHEM
4679
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
HSDB
7292
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
DRUG BANK
DB00213
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
RXCUI
40790
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY RxNorm
LACTMED
Pantoprazole
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
CAS
102625-70-7
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
EPA CompTox
102625-70-7
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
IUPHAR
7260
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
EVMPD
SUB09608MIG
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
DRUG CENTRAL
2054
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
MERCK INDEX
M8387
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY Merck Index
MESH
C064276
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
NCI_THESAURUS
C29346
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
INN
6548
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL1502
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
FDA UNII
D8TST4O562
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
PRIMARY
CAS
154644-14-1
Created by admin on Fri Jun 25 22:01:15 UTC 2021 , Edited by admin on Fri Jun 25 22:01:15 UTC 2021
SUPERSEDED