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Details

Stereochemistry RACEMIC
Molecular Formula C16H14F2N3O4S.Na
Molecular Weight 405.352
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE SODIUM ANHYDROUS

SMILES

[Na+].COC1=CC=NC(C[S+]([O-])C2=NC3=C([N-]2)C=C(OC(F)F)C=C3)=C1OC

InChI

InChIKey=YNWDKZIIWCEDEE-UHFFFAOYSA-N
InChI=1S/C16H14F2N3O4S.Na/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;/q-1;+1

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

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
Comparison of pantoprazole 20 mg to ranitidine 150 mg b.i.d. in the treatment of mild gastroesophageal reflux disease.
2001
[H2 receptor antagonists and proton pump inhibitors: principles and rules of use].
2001 Apr 15
Dyspepsia: challenges in diagnosis and selection of treatment.
2001 Aug
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
Bioavailability of a crushed pantoprazole tablet after buffering with sodium hydrogencarbonate or magaldrate relative to the intact enteric coated pantoprazole tablet.
2001 Jan-Feb
Persistent eradication of Helicobacter pylori after systemic politherapy associated with periodontal pockets treatment with metronidazole and calcium sulphate.
2001 Jul-Aug
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
Proton pump inhibitors: a study of GPs' prescribing.
2001 Jun
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
Is there any relationship between functional dyspepsia and chronic gastritis associated with Helicobacter pylori infection?
2001 Mar-Apr
Proton pump inhibitors and their drug interactions: an evidence-based approach.
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
Effect of aggressive therapy on laryngeal symptoms and voice characteristics in patients with gastroesophageal reflux.
2001 Oct
[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
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
Nonallergic anaphylaxis to pantoprazole.
2002 Feb
Protonix. First i.v. proton pump inhibitor approved.
2002 Feb
Conformational analysis: a new approach by means of chemometrics.
2002 Jan 30
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
Drug points: Severe myalgia from an interaction between treatments with pantoprazole and methotrexate.
2002 Jun 22
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
Combination drug therapy for gastroesophageal reflux disease.
2002 May
Stability of pantoprazole in an extemporaneously compounded oral liquid.
2002 May 15
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.
Name Type Language
PANTOPRAZOLE SODIUM ANHYDROUS
WHO-DD  
Common Name English
PANTOPRAZOLE SODIUM SALT [MI]
Common Name English
1H-BENZIMIDAZOLE, 6-(DIFLUOROMETHOXY)-2-(((3,4-DIMETHOXY-2-PYRIDINYL)METHYL)SULFINYL)-, SODIUM SALT (1:1)
Systematic Name English
Pantoprazole sodium anhydrous [WHO-DD]
Common Name English
PANTOPRAZOLE SODIUM SALT
MI  
Common Name English
Code System Code Type Description
CAS
138786-67-1
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY
MERCK INDEX
m8387
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY Merck Index
PUBCHEM
15008962
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID7044215
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY
EVMPD
SUB26257
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY
FDA UNII
S9363155XL
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY
SMS_ID
100000090359
Created by admin on Fri Dec 15 19:13:34 GMT 2023 , Edited by admin on Fri Dec 15 19:13:34 GMT 2023
PRIMARY