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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14F2N3O3S
Molecular Weight 366.362
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of 9-(DIFLUOROMETHOXY)-3,4-DIMETHOXY-5H-PYRIDO(1',2':4,5)(1,2,4)THIADIAZINO(2,3-A)BENZIMIDAZOL-13-IUM

SMILES

COC1=CC=[N+]2C3=NC4=C(C=C(OC(F)F)C=C4)N3SCC2=C1OC

InChI

InChIKey=MKKLIANODHXTFO-UHFFFAOYSA-N
InChI=1S/C16H14F2N3O3S/c1-22-13-5-6-20-12(14(13)23-2)8-25-21-11-7-9(24-15(17)18)3-4-10(11)19-16(20)21/h3-7,15H,8H2,1-2H3/q+1

HIDE SMILES / InChI

Molecular Formula C16H14F2N3O3S
Molecular Weight 366.362
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
Lansoprazole: an update of its place in the management of acid-related disorders.
2001
Comparison of pantoprazole 20 mg to ranitidine 150 mg b.i.d. in the treatment of mild gastroesophageal reflux disease.
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
Pharmacokinetics of pantoprazole in patients with moderate and severe hepatic dysfunction.
2001 Aug
Dyspepsia: challenges in diagnosis and selection of treatment.
2001 Aug
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
Replacement of oral proton pump inhibitors with intravenous pantoprazole to effectively control gastric acid hypersecretion in patients with Zollinger-Ellison syndrome.
2001 Dec
Oral pantoprazole for acid suppression in the treatment of patients with Zollinger-Ellison syndrome.
2001 Dec
Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein.
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
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
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
Possible phototoxicity with subsequent progression to discoid lupus following pantoprazole administration.
2001 Jul
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
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
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
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
Comparable clinical efficacy and tolerability of 20 mg pantoprazole and 20 mg omeprazole in patients with grade I reflux oesophagitis.
2001 Oct
Influence of pantoprazole on oesophageal motility, and bile and acid reflux in patients with oesophagitis.
2001 Sep
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
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
Pantoprazole IV (Protonix IV).
2002 Apr 29
Nonallergic anaphylaxis to pantoprazole.
2002 Feb
Protonix. First i.v. proton pump inhibitor approved.
2002 Feb
Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography.
2002 Jan 5
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
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
[Correlation of Barrett's esophagus and colonic adenomas].
2002 Jun 9
[Intravenous 3-day Helicobacter pylori eradication therapy is highly effective in patients with bleeding peptic ulcer].
2002 Jun-Jul
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
Factors associated with treatment failure of Helicobacter pylori infection in a developing country.
2002 Oct
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 Sat Dec 16 14:24:50 GMT 2023
Edited
by admin
on Sat Dec 16 14:24:50 GMT 2023
Record UNII
U5H68DGQ8L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
9-(DIFLUOROMETHOXY)-3,4-DIMETHOXY-5H-PYRIDO(1',2':4,5)(1,2,4)THIADIAZINO(2,3-A)BENZIMIDAZOL-13-IUM
Systematic Name English
5H-PYRIDO(1',2':4,5)(1,2,4)THIADIAZINO(2,3-A)BENZIMIDAZOL-13-IUM, 9-(DIFLUOROMETHOXY)-3,4-DIMETHOXY-
Systematic Name English
PANTOPRAZOLE METABOLITE ACTIVE SULFENAMIDE
Common Name English
Code System Code Type Description
PUBCHEM
15163517
Created by admin on Sat Dec 16 14:24:51 GMT 2023 , Edited by admin on Sat Dec 16 14:24:51 GMT 2023
PRIMARY
CAS
138786-74-0
Created by admin on Sat Dec 16 14:24:51 GMT 2023 , Edited by admin on Sat Dec 16 14:24:51 GMT 2023
PRIMARY
FDA UNII
U5H68DGQ8L
Created by admin on Sat Dec 16 14:24:51 GMT 2023 , Edited by admin on Sat Dec 16 14:24:51 GMT 2023
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE