U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C16H15F2N3O4S
Molecular Weight 383.37
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE

SMILES

COC1=C(OC)C(C[S+]([O-])C2=NC3=C(N2)C=C(OC(F)F)C=C3)=NC=C1

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 383.37
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2000
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

2000
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
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.
2000 Oct
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.
2001
Pantoprazole and cyclosporine or tacrolimus.
2001 Apr
No clinical benefit of adding cisapride to pantoprazole for treatment of gastro-oesophageal reflux disease.
2001 Aug
Oral pantoprazole for acid suppression in the treatment of patients with Zollinger-Ellison syndrome.
2001 Dec
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
Switching between intravenous and oral pantoprazole.
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
[Role of Helicobacter pylori infection in insulin-dependent diabetes mellitus].
2001 Jun
Fish oil (Eicosapen) is less effective than metronidazole, in combination with pantoprazole and clarithromycin, for Helicobacter pylori eradication.
2001 Jun
Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes.
2001 Jun
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin.
2001 Mar
Is there any relationship between functional dyspepsia and chronic gastritis associated with Helicobacter pylori infection?
2001 Mar-Apr
Cluster headache without autonomic symptoms?
2001 Nov
A comparison of simplified lansoprazole suspension administered nasogastrically and pantoprazole administered intravenously: effects on 24-h intragastric pH.
2001 Nov
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
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
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
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
[Correlation of Barrett's esophagus and colonic adenomas].
2002 Jun 9
Proton pump activation in stimulated parietal cells is regulated by gastric acid secretory capacity: a human study.
2002 May
Stability of pantoprazole in an extemporaneously compounded oral liquid.
2002 May 15
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:07:32 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:32 GMT 2025
Record UNII
D8TST4O562
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PANTOCID
Preferred Name English
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 [VANDF]
Common Name English
BY-1023
Code English
PANTOPRAZOLE [MART.]
Common Name English
PANTOZOL
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
BY1023
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
Pantoprazole [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175525
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
WHO-VATC QA02BD04
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
WHO-VATC QA02BC02
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
NDF-RT N0000000147
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
EMA ASSESSMENT REPORTS SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
NCI_THESAURUS C29723
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
WHO-ATC A02BD04
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
EMA ASSESSMENT REPORTS PANTOLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
WHO-ATC A02BD11
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
WHO-ATC A02BC02
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
EMA ASSESSMENT REPORTS CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
EMA ASSESSMENT REPORTS PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
EMA ASSESSMENT REPORTS PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
LIVERTOX NBK548461
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
Code System Code Type Description
WIKIPEDIA
PANTOPRAZOLE
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
PUBCHEM
4679
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
HSDB
7292
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
DRUG BANK
DB00213
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
RXCUI
40790
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY RxNorm
LACTMED
Pantoprazole
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
CAS
102625-70-7
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
NSC
759257
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID4023416
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
IUPHAR
7260
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
EVMPD
SUB09608MIG
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
CHEBI
7915
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
DRUG CENTRAL
2054
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
MERCK INDEX
m8387
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY Merck Index
DAILYMED
D8TST4O562
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
MESH
C064276
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
NCI_THESAURUS
C29346
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
INN
6548
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
ChEMBL
CHEMBL1502
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
SMS_ID
100000092491
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
FDA UNII
D8TST4O562
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
USAN
DD-26
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
PRIMARY
CAS
154644-14-1
Created by admin on Mon Mar 31 18:07:32 GMT 2025 , Edited by admin on Mon Mar 31 18:07:32 GMT 2025
SUPERSEDED
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
PLASMA
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC