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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 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 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

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
Lansoprazole: an update of its place in the management of acid-related disorders.
2001
Dyspepsia: challenges in diagnosis and selection of treatment.
2001 Aug
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
Amoxycillin, clarithromycin and either sucralfate or pantoprazole for eradication of Helicobacter pylori in duodenal ulcer (a randomized controlled trial).
2001 Dec 17
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.
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
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
Effects on 24-hour intragastric pH: a comparison of lansoprazole administered nasogastrically in apple juice and pantoprazole administered intravenously.
2001 Jul
Cure of Helicobacter pylori infection in elderly patients: comparison of low versus high doses of clarithromycin in combination with amoxicillin and pantoprazole.
2001 Jul
Predictors of failure of Helicobacter pylori eradication with the standard 'Maastricht triple therapy'.
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
Proton pump inhibitors: a study of GPs' prescribing.
2001 Jun
Is there any relationship between functional dyspepsia and chronic gastritis associated with Helicobacter pylori infection?
2001 Mar-Apr
Shortcomings of the first-generation proton pump inhibitors.
2001 May
Proton pump inhibitors and their drug interactions: an evidence-based approach.
2001 May
Resolution of granulomatous rosacea after eradication of Helicobacter pylori with clarithromycin, metronidazole and pantoprazole.
2001 Nov
Systematic review of proton pump inhibitors for the acute treatment of reflux oesophagitis.
2001 Nov
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
[Microflora of gastric juice in patients after eradication of Helicobacter pylori and treatment with a proton pump inhibitor].
2002
Efficacy of quadruple therapy with pantoprazole, bismuth, tetracycline and metronidazole as rescue treatment for Helicobacter pylori infection.
2002 Aug
Protonix. First i.v. proton pump inhibitor approved.
2002 Feb
Gateways to clinical trials.
2002 Jan-Feb
Proton pump inhibitors: an update.
2002 Jul 15
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
Different effects of short-term omeprazole, lansoprazole or pantoprazole on the accuracy of the (13)C-urea breath test.
2002 Mar
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 Thu Jul 06 01:59:28 UTC 2023
Edited
by admin
on Thu Jul 06 01:59:28 UTC 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 Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
NCI_THESAURUS C29723
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
EMA ASSESSMENT REPORTS PANTECTA CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
EMA ASSESSMENT REPORTS CONTROLOC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
EMA ASSESSMENT REPORTS SOMAC CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
EMA ASSESSMENT REPORTS PANTOZOL CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID90936960
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
PUBCHEM
11954257
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
USAN
LL-37
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
DRUG BANK
DBSALT000386
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
SMS_ID
100000091062
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
RXCUI
236632
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
FDA UNII
6871619Q5X
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
EVMPD
SUB03624MIG
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
CAS
164579-32-2
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
NCI_THESAURUS
C61877
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
EVMPD
SUB21564
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL1502
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
RXCUI
253191
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
ALTERNATIVE
CHEBI
50270
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
DAILYMED
6871619Q5X
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
RS_ITEM_NUM
1494895
Created by admin on Thu Jul 06 01:59:28 UTC 2023 , Edited by admin on Thu Jul 06 01:59:28 UTC 2023
PRIMARY
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ACTIVE MOIETY