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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
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.
2000 Oct
Comparison of pantoprazole 20 mg to ranitidine 150 mg b.i.d. in the treatment of mild gastroesophageal reflux disease.
2001
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.
2001
Pharmacokinetics of pantoprazole in patients with moderate and severe hepatic dysfunction.
2001 Aug
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
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.
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
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?
2001 Jan
Switching between intravenous and oral pantoprazole.
2001 Jan
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
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
Pharmacodynamic effects and kinetic disposition of rabeprazole in relation to CYP2C19 genotypes.
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
Reversible pheripheral edema in female patients taking proton pump inhibitors for peptic acid diseases.
2001 May
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
Comparable clinical efficacy and tolerability of 20 mg pantoprazole and 20 mg omeprazole in patients with grade I reflux oesophagitis.
2001 Oct
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
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
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
Acid suppression in healthy subjects following lansoprazole or pantoprazole.
2002 Mar
Review article: rabeprazole-based therapy in Helicobacter pylori eradication.
2002 Mar
Combination drug therapy for gastroesophageal reflux disease.
2002 May
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 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