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Details

Stereochemistry RACEMIC
Molecular Formula 2C16H14F2N3O4S.2Na.3H2O
Molecular Weight 864.7525
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE SODIUM

SMILES

COc1ccnc(CS(=O)c2nc3ccc(cc3[n-]2)OC(F)F)c1OC.COc1ccnc(CS(=O)c2nc3ccc(cc3[n-]2)OC(F)F)c1OC.[Na+].[Na+].O.O.O

InChI

InChIKey=VNKNFEINTHUQGZ-UHFFFAOYSA-N
InChI=1S/2C16H14F2N3O4S.2Na.3H2O/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;;;3*1H2/q2*-1;2*+1;;;

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Proton pump inhibitors and gastric acid secretion.
2001 Dec
Oral pantoprazole for acid suppression in the treatment of patients with Zollinger-Ellison syndrome.
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
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
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
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.
2001 May
Shortcomings of the first-generation proton pump inhibitors.
2001 May
Cluster headache without autonomic symptoms?
2001 Nov
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
[Comparative study of proton pump inhibitors].
2001 Sep 9
[Submicroscopic aspects of the mechanism of inhibitors of H+/K+-ATPase in gastric parietal cells].
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
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
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
Gateways to clinical trials.
2002 Jan-Feb
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
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
[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
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 20:58:44 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:44 UTC 2021
Record UNII
6871619Q5X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PANTOPRAZOLE SODIUM
MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
PANTOPRAZOLE SODIUM SESQUIHYDRATE [WHO-DD]
Common Name English
PANTOPRAZOLE SODIUM [MART.]
Common Name English
5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE, SODIUM SALT, SESQUIHYDRATE
Common Name English
PANTOPRAZOLE (AS SODIUM)
Common Name English
PANTOPRAZOLE SODIUM [VANDF]
Common Name English
PANTOPRAZOLE SODIUM [USAN]
Common Name English
PANTOPRAZOLE SODIUM [USP-RS]
Common Name English
SODIUM 5-(DIFLUOROMETHOXY)-2-((RS)-((3,4-DIMETHOXYPYRIDIN-2-YL)METHYL)SULFINYL)BENZIMIDAZOL-1-IDE SESQUIHYDRATE
Common Name English
PROTONIX
Brand Name English
SOMAC CONTROL
Brand Name English
PANTOPRAZOLE SODIUM [ORANGE BOOK]
Common Name English
PANTOPRAZOLE SODIUM HYDRATE
JAN  
Common Name English
1H-BENZIMIDAZOLE, 5-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDYL)METHYL)SULFINYL)-, SODIUM SALT, HYDRATE (2:3)
Common Name English
CONTROLOC CONTROL
Brand Name English
PANTOPRAZOLE SODIUM SESQUIHYDRATE [EP MONOGRAPH]
Common Name English
PANTOPRAZOLE SODIUM [USP MONOGRAPH]
Common Name English
PANTOPRAZOLE SODIUM HYDRATE [JAN]
Common Name English
1H-BENZIMIDAZOLE, 6-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDINYL)METHYL)SULFINYL)-, SODIUM SALT, HYDRATE (2:2:3)
Systematic Name English
PANTOZOL CONTROL
Brand Name English
PANTOPRAZOLE SODIUM SESQUIHYDRATE
EP   WHO-DD  
Common Name English
PANTOPRAZOLE (AS SODIUM SESQUIHYDRATE)
Common Name English
PANTOLOC CONTROL
Brand Name English
PANTOPRAZOLE SODIUM [USP]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS PANTOLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
NCI_THESAURUS C29723
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
EMA ASSESSMENT REPORTS PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
EMA ASSESSMENT REPORTS CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
EMA ASSESSMENT REPORTS SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
EMA ASSESSMENT REPORTS PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
Code System Code Type Description
USP_CATALOG
1494895
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY USP-RS
PUBCHEM
11954257
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
DRUG BANK
DBSALT000386
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
RXCUI
236632
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
FDA UNII
6871619Q5X
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
EVMPD
SUB03624MIG
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
CAS
164579-32-2
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
NCI_THESAURUS
C61877
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
EVMPD
SUB21564
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL1502
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
PRIMARY
RXCUI
253191
Created by admin on Fri Jun 25 20:58:45 UTC 2021 , Edited by admin on Fri Jun 25 20:58:45 UTC 2021
ALTERNATIVE
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
PARENT -> SALT/SOLVATE
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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At 305 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Sum of related compounds D and F-0.2 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
sum of impurities D and F- 0.2 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Sum of related compounds D and F-0.2 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
sum of impurities D and F- 0.2 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY