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

Molecular Formula C16H15F2N3O4S
Molecular Weight 383.3715
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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

971827200000
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

971827200000
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 >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
yes
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
minor
minor
yes
yes
PubMed

PubMed

TitleDatePubMed
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:01:15 UTC 2021
Edited
by admin
on Fri Jun 25 22:01:15 UTC 2021
Record UNII
D8TST4O562
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC