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Details

Stereochemistry RACEMIC
Molecular Formula 2C16H14F2N3O4S.Mg
Molecular Weight 789.029
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOPRAZOLE MAGNESIUM

SMILES

[Mg++].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=RDRUTBCDIVCMMX-UHFFFAOYSA-N
InChI=1S/2C16H14F2N3O4S.Mg/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;/q2*-1;+2

HIDE SMILES / InChI

Molecular Formula Mg
Molecular Weight 24.305
Charge 2
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

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
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
Effect of inhibition of gastric acid secretion on antropyloroduodenal motor activity and duodenal acid hypersensitivity in functional dyspepsia.
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
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
Bioavailability of a crushed pantoprazole tablet after buffering with sodium hydrogencarbonate or magaldrate relative to the intact enteric coated pantoprazole tablet.
2001 Jan-Feb
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
Cure of Helicobacter pylori infection in elderly patients: comparison of low versus high doses of clarithromycin in combination with amoxicillin and pantoprazole.
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
Functionally impaired, hypertrophic ECL cells accumulate vacuoles and lipofuscin bodies. An ultrastructural study of ECL cells isolated from hypergastrinemic rats.
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
Reversible pheripheral edema in female patients taking proton pump inhibitors for peptic acid diseases.
2001 May
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
[Submicroscopic aspects of the mechanism of inhibitors of H+/K+-ATPase in gastric parietal cells].
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
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
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
Conformational analysis: a new approach by means of chemometrics.
2002 Jan 30
Early relief of upper gastrointestinal dyspeptic symptoms: a survey of empirical therapy with pantoprazole in Canadian clinical practice.
2002 Jul
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
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
Long-term clinical outcome of elderly patients with reflux esophagitis: a six-month to three-year follow-up study.
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
[Correlation of Barrett's esophagus and colonic adenomas].
2002 Jun 9
Acid suppression in healthy subjects following lansoprazole or pantoprazole.
2002 Mar
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 17:58:22 GMT 2023
Edited
by admin
on Fri Dec 15 17:58:22 GMT 2023
Record UNII
1AL13B11R4
Record Status Validated (UNII)
Record Version
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Name Type Language
PANTOPRAZOLE MAGNESIUM
WHO-DD  
Common Name English
Pantoprazole magnesium [WHO-DD]
Common Name English
PANTOPRAZOLE HEMIMAGNESIUM
Common Name English
MAGNESIUM PANTOPRAZOLE
Common Name English
Code System Code Type Description
FDA UNII
1AL13B11R4
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
EVMPD
SUB22265
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
DRUG BANK
DBSALT000853
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
CAS
199387-73-0
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
PUBCHEM
71587624
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
SMS_ID
100000085425
Created by admin on Fri Dec 15 17:58:22 GMT 2023 , Edited by admin on Fri Dec 15 17:58:22 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE