Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Optical Activity | ( - ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(NC(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1
InChI
InChIKey=SUBDBMMJDZJVOS-DEOSSOPVSA-N
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Esomeprazole strontium is a proton pump inhibitor. It suppresses gastric acid secretion by specific inhibition H+/K+ ATPase in the gastric parietal cell. The S- and R-isomers of omeprazole are protonated and converted in the acidic compartment of the parietal cell forming the active inhibitor, the achiral sulphenamide. By acting specifically on the proton pump, esomeprazole blocks the final step in acid production, thus reducing gastric acidity. The drug is indicated for the treatment of gastroesophageal reflux disease, reduction the risk of NSAID-associated gastric ulcer, eradication of H.pylori, and pathological hypersecretory conditions.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
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7.5 μM |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.2 μM × h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
strong [IC50 3.7 uM] | yes (co-administration study) Comment: Esomeprazole administration resulted in a significant increase (1.67‐fold) in the AUC0–∞ of proguanil and a significant decrease (0.522‐fold) in that of cycloguanil |
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weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
yes [IC50 1.2 uM] | likely (co-administration study) Comment: The frequency of delayed MTX elimination in patients administered esomeprazole was 71.4% Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/ |
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yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (co-administration study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations |
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yes | yes (pharmacogenomic study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations; The CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15–20% of Asians lack CYP2C19 and are termed poor metabolizers. At steady state, the ratio of AUC in poor metabolizers to AUC in the rest of the population (normal metabolizers) is approximately 2 |
PubMed
Title | Date | PubMed |
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Omeprazole-induced acute interstitial nephritis. | 1999 Nov |
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Pharmacokinetic study of esomeprazole in the elderly. | 2001 |
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Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole? | 2001 Apr |
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Antireflux surgery in children suffering from reflux-associated respiratory disease? | 2001 Apr |
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Pantoprazole and cyclosporine or tacrolimus. | 2001 Apr |
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Maximal acid reflux control for Barrett's oesophagus: feasible and effective. | 2001 Apr |
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Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance. | 2001 Apr |
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Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue. | 2001 Apr |
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A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 2001 Apr |
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Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection. | 2001 Apr 1 |
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From the Food and Drug Administration. | 2001 Apr 4 |
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Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats. | 2001 Feb |
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Improved high performance liquid chromatographic analysis of omeprazole in human plasma. | 2001 Feb |
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Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression. | 2001 Feb |
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Recurrent ulcer bleeding: is intravenous omeprazole the solution? | 2001 Feb |
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Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy. | 2001 Feb |
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Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 2001 Feb |
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Aggressive acid control: minimizing progression of Barrett's esophagus. | 2001 Feb |
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Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease. | 2001 Feb |
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Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase. | 2001 Feb |
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Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection. | 2001 Feb 2 |
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[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege]. | 2001 Jan |
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Esomeprazole once daily for 6 months is effective therapy for maintaining healed erosive esophagitis and for controlling gastroesophageal reflux disease symptoms: a randomized, double-blind, placebo-controlled study of efficacy and safety. | 2001 Jan |
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Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis. | 2001 Jan |
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Helicobacter pylori effects on gastritis, gastrin and enterochromaffin-like cells in Zollinger-Ellison syndrome and non-Zollinger-Ellison syndrome acid hypersecretors treated long-term with lansoprazole. | 2001 Jan |
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Accuracy of the stool antigen test in the diagnosis of Helicobacter pylori infection before treatment and in patients on omeprazole therapy. | 2001 Jan |
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Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis. | 2001 Jan 15 |
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Helicobacter pylori and nonsteroidal anti-inflammatory drugs: interaction with proton pump inhibitor therapy for prevention of nonsteroidal anti-inflammatory drug ulcers and ulcer complications--future research needs. | 2001 Jan 8 |
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Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases? | 2001 Jan-Feb |
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The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
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Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals. | 2001 Mar |
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Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial. | 2001 Mar |
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Pharmacodynamic modeling of lansoprazole using an indirect irreversible response model. | 2001 Mar |
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Effect of genotypic differences in CYP2C19 on cure rates for Helicobacter pylori infection by triple therapy with a proton pump inhibitor, amoxicillin, and clarithromycin. | 2001 Mar |
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Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin. | 2001 Mar |
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Esomeprazole 20 mg maintains symptom control in endoscopy-negative gastro-oesophageal reflux disease: a controlled trial of 'on-demand' therapy for 6 months. | 2001 Mar |
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[Heartburn. Only a harmless symptom?]. | 2001 Mar 8 |
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Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice. | 2001 Mar 9 |
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New OTC drugs and devices 2000: a selective review. | 2001 Mar-Apr |
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Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication. | 2001 Mar-Apr |
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c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma. | 2001 Mar-Apr |
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 23:08:08 UTC 2023
by
admin
on
Thu Jul 06 23:08:08 UTC 2023
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Record UNII |
N3PA6559FT
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QB01AC56
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WHO-ATC |
B01AC56
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WHO-ATC |
A02BC05
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NDF-RT |
N0000175525
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WHO-VATC |
QM01AE52
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WHO-ATC |
A02BD06
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LIVERTOX |
370
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WHO-ATC |
M01AE52
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NDF-RT |
N0000000147
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WHO-VATC |
QA02BC05
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NCI_THESAURUS |
C29723
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FDA ORPHAN DRUG |
684119
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WHO-VATC |
QA02BD06
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EMA ASSESSMENT REPORTS | NEXIUM CONTROL (AUTHOIRIZED: GASTROESOPHAGEAL REFLUX) |
Code System | Code | Type | Description | ||
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M8209
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PRIMARY | Merck Index | ||
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5488
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8158
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1055
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PRIMARY | |||
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N0000182140
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PRIMARY | Cytochrome P450 2C19 Inhibitors [MoA] | ||
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N3PA6559FT
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CHEMBL1201320
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9568614
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283742
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PRIMARY | RxNorm | ||
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DB00736
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100000087252
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ESOMEPRAZOLE
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SUB01960MIG
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DTXSID4044292
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Esomeprazole
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7766
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50275
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C65538
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119141-88-7
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N3PA6559FT
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D064098
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT |
Metabolism of esomeprazole occurs via the hepatic CYP isoforms CYP2C19 and CYP3A4, which produce the 2 main pharmacologically inactive hydroxy and sulphone metabolites, respectively
MAJOR
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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PEDIATRICS PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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CHILDREN |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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