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Details

Stereochemistry RACEMIC
Molecular Formula 2C16H14F2N3O4S.2Na.3H2O
Molecular Weight 864.749
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE SODIUM

SMILES

O.O.O.[Na+].[Na+].COC1=CC=NC(C[S+]([O-])C2=NC3=C([N-]2)C=C(OC(F)F)C=C3)=C1OC.COC4=CC=NC(C[S+]([O-])C5=NC6=C([N-]5)C=C(OC(F)F)C=C6)=C4OC

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

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

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
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality.
2001
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.
2001
[H2 receptor antagonists and proton pump inhibitors: principles and rules of use].
2001 Apr 15
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
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.
2001 Feb
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
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
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
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
Pantoprazole versus lansoprazole in French patients with reflux esophagitis.
2001 Mar
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin.
2001 Mar
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.
2001 Mar 9
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.
2001 May
Cluster headache without autonomic symptoms?
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
Comparable clinical efficacy and tolerability of 20 mg pantoprazole and 20 mg omeprazole in patients with grade I reflux oesophagitis.
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
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
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
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
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
[Intravenous 3-day Helicobacter pylori eradication therapy is highly effective in patients with bleeding peptic ulcer].
2002 Jun-Jul
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 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 Fri Dec 15 18:48:36 GMT 2023
Edited
by admin
on Fri Dec 15 18:48:36 GMT 2023
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 [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 sesquihydrate [WHO-DD]
Common Name English
PANTOPRAZOLE SODIUM HYDRATE
JAN  
Common Name English
PANTOPRAZOLE SODIUM [USP IMPURITY]
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
Classification Tree Code System Code
EMA ASSESSMENT REPORTS PANTOLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
NCI_THESAURUS C29723
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
EMA ASSESSMENT REPORTS PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
EMA ASSESSMENT REPORTS CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
EMA ASSESSMENT REPORTS SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
EMA ASSESSMENT REPORTS PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90936960
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
PUBCHEM
11954257
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
USAN
LL-37
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
DRUG BANK
DBSALT000386
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
SMS_ID
100000091062
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
RXCUI
236632
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
FDA UNII
6871619Q5X
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
EVMPD
SUB03624MIG
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
CAS
164579-32-2
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
NCI_THESAURUS
C61877
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
EVMPD
SUB21564
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL1502
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
RXCUI
253191
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
ALTERNATIVE
CHEBI
50270
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
DAILYMED
6871619Q5X
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
RS_ITEM_NUM
1494895
Created by admin on Fri Dec 15 18:48:36 GMT 2023 , Edited by admin on Fri Dec 15 18:48:36 GMT 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
At 305 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP