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Details

Stereochemistry MIXED
Molecular Formula 2C16H14F2N3O4S.Mg.2H2O
Molecular Weight 825.059
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pantoprazole Magnesium dihydrate

SMILES

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

InChI

InChIKey=HBYMHJOUGBMDHH-UHFFFAOYSA-N
InChI=1S/2C16H14F2N3O4S.Mg.2H2O/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;;2*1H2/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 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 C16H14F2N3O4S
Molecular Weight 382.362
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
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
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
Proton pump inhibitors and gastric acid secretion.
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
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.
2001 Feb
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
Predictors of failure of Helicobacter pylori eradication with the standard 'Maastricht triple therapy'.
2001 Jul
[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
Pharmacological and pharmacodynamic essentials of H(2)-receptor antagonists and proton pump inhibitors for the practising physician.
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
Pantoprazole versus lansoprazole in French patients with reflux esophagitis.
2001 Mar
Functionally impaired, hypertrophic ECL cells accumulate vacuoles and lipofuscin bodies. An ultrastructural study of ECL cells isolated from hypergastrinemic rats.
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
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
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
Comparable clinical efficacy and tolerability of 20 mg pantoprazole and 20 mg omeprazole in patients with grade I reflux oesophagitis.
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
Effect of pantoprazole versus other proton pump inhibitors on 24-hour intragastric pH and basal acid output in Zollinger-Ellison syndrome.
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
Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography.
2002 Jan 5
Gateways to clinical trials.
2002 Jan-Feb
Pantoprazole-induced recurrent anaphylactic shock.
2002 Jun
Intravenous proton pump inhibitors in the critical care setting.
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
Review article: rabeprazole-based therapy in Helicobacter pylori eradication.
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
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 23:58:44 UTC 2023
Edited
by admin
on Thu Jul 06 23:58:44 UTC 2023
Record UNII
9G7ZX364TY
Record Status Validated (UNII)
Record Version
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Name Type Language
Pantoprazole Magnesium dihydrate
Common Name English
1H-Benzimidazole, 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-, magnesium salt, hydrate
Systematic Name English
1H-Benzimidazole, 6-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-, magnesium salt, hydrate (2:1:2)
Systematic Name English
Code System Code Type Description
PUBCHEM
164512899
Created by admin on Thu Jul 06 23:58:45 UTC 2023 , Edited by admin on Thu Jul 06 23:58:45 UTC 2023
PRIMARY
FDA UNII
9G7ZX364TY
Created by admin on Thu Jul 06 23:58:45 UTC 2023 , Edited by admin on Thu Jul 06 23:58:45 UTC 2023
PRIMARY
CAS
471293-63-7
Created by admin on Thu Jul 06 23:58:45 UTC 2023 , Edited by admin on Thu Jul 06 23:58:45 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY