3,10-DIMETHOXY-2,4-DIMETHYL-5H-BENZO(4,5)IMIDAZO(1,2-B)PYRIDO(1,2-D)(1,2,4)THIADIAZIN-13-IUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18N3O2S
Molecular Weight	328.409
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure of 3,10-DIMETHOXY-2,4-DIMETHYL-5H-BENZO(4,5)IMIDAZO(1,2-B)PYRIDO(1,2-D)(1,2,4)THIADIAZIN-13-IUM

Structure Search

SMILES

COC1=CC=C2N3SCC4=C(C)C(OC)=C(C)C=[N+]4C3=NC2=C1

InChI

InChIKey=ULDYIZLGTORGDF-UHFFFAOYSA-N

InChI=1S/C17H18N3O2S/c1-10-8-19-15(11(2)16(10)22-4)9-23-20-14-6-5-12(21-3)7-13(14)18-17(19)20/h5-8H,9H2,1-4H3/q+1

HIDE SMILES / InChI

Molecular Formula	C17H18N3O2S
Molecular Weight	328.409
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 38 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411559	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Heartburn 24 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=477cfda2-44cf-4d0e-bdc4-e30bf16bfea9	Primary	Approved 8583	NEXIUM 24HR Approved Use treats frequent heartburn (occurs 2 or more days a week) Launch Date 2014
Duodenal ulcer 49 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8583	PRILOSEC Approved Use PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date 2008
Gastric ulcer 74 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8583	PRILOSEC Approved Use PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date 2008
Gastroesophageal reflux disease 68 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8583	PRILOSEC Approved Use PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date 1989
Pathological hypersecretory conditions 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8583	PRILOSEC Approved Use PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date 2008

C_max

Value	Dose	Co-administered	Analyte	Population
668 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		OMEPRAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
7.5 μM EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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	Analyte	Population
1200 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217	20 mg single, oral dose: 20 mg route of administration: oral experiment type: single co-administered:	OMEPRAZOLE plasma	Homo sapiens population: healthy age: adults sex: food status:
1220 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	OMEPRAZOLE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
1179 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OMEPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
16.2 μM × h EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.58 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OMEPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.4 h EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/	unhealthy, 45.2 Health Status: unhealthy Age Group: 45.2 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/	Other AEs: Nausea, Diarrhoea... Other AEs: Nausea (7%) Diarrhoea (6%) Headache (3%) Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	Other AEs: Headache, Abdominal pain... Other AEs: Headache (6.9%) Abdominal pain (5.2%) Nausea (4%) Diarrhea (3.7%) Vomiting (3.2%) Flatulence (2.7%) Esophageal acid reflux (1.9%) Upper respiratory infection (1.9%) Constipation (1.5%) Dizziness (1.5%) Rash (1.5%) Asthenia (1.3%) Back pain (1.1%) Cough (1.1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP2C19 2057 CYP1A2 2153 BCRP 910 OATP1B1 1079 OAT3 747 OAT1 725 MATE1 415 MATE2 267 OCT2 779 OCT1 620 OCT3 159 CYP2B6 926 CYP2C8 1057	P-gp 2052 CYP2C19 1119 CYP2C8 810 CYP2C18 149	MRP3 83 CYP1A1 151 CYP1A2 832 CYP1B1 71

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/ \| https://pubmed.ncbi.nlm.nih.gov/30845361/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/ \| https://pubmed.ncbi.nlm.nih.gov/30845361/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16248835/ \| https://pubmed.ncbi.nlm.nih.gov/10584979/	weak [Ki 150 uM]	weak (co-administration study) Comment: Omeprazole exerts a concentration-dependent inhibition of CYP1A2 activity in man. However, even after single oral doses up to 80 mg, this effect is weak and without clinical relevance Sources: https://pubmed.ncbi.nlm.nih.gov/16248835/ \| https://pubmed.ncbi.nlm.nih.gov/10584979/
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	weak [Ki 367.5 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	weak [Ki 745.1 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/	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/
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 15.7 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19076159/	yes [IC50 17.6 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	yes [IC50 17.7 uM]
OCT3 161	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 22 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 4.32 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 6.7 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 6.8 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25975815/	yes [IC50 84.3 uM]	unlikely (co-administration study) Comment: Coaministration with simvastatin acid unlikely results in DDIs Sources: https://pubmed.ncbi.nlm.nih.gov/25975815/
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16248835/ \| https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf	yes [Ki 7.1 uM]	yes (co-administration study) Comment: Omeprazole increased Cmax and AUC of cilostazol by 18% and 26% respectively Sources: https://pubmed.ncbi.nlm.nih.gov/16248835/ \| https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/10445394/	yes
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP1B1 93	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	yes
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MATE2 267	inhibitor 4027 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MRP1 232	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/30349304/	yes
P-gp 1932	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/33049093/ \| https://pubmed.ncbi.nlm.nih.gov/30349304/	yes
MRP3 326	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/	yes	yes (expression study) Comment: livers of patients treated with omeprazole showed higher MRP3 protein expression Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16093273/ \| https://pubmed.ncbi.nlm.nih.gov/9353355/ \| https://pubmed.ncbi.nlm.nih.gov/10901708/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf	major	yes (co-administration study) Comment: When voriconazole was given with omeprazole to healthy subjects, it significantly increased the steady-state Cmax and AUC0-24 of omeprazole, an average of 2 times and 4 times, respectively Sources: https://pubmed.ncbi.nlm.nih.gov/16093273/ \| https://pubmed.ncbi.nlm.nih.gov/9353355/ \| https://pubmed.ncbi.nlm.nih.gov/10901708/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16093273/ \| https://pubmed.ncbi.nlm.nih.gov/9353355/ \| https://pubmed.ncbi.nlm.nih.gov/10901708/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf	major	yes (co-administration study) Comment: Drugs known to induce CYP2C19 or CYP3A4 (such as rifampin) may lead to decreased omeprazole serum levels. In a cross-over study in 12 healthy male subjects, St John’s wort, an inducer of CYP3A4, decreased the systemic exposure of omeprazole in CYP2C19 poor metabolisers (Cmax and AUC decreased by 37.5% and 37.9%, respectively) and extensive metabolisers (Cmax and AUC decreased by 49.6% and 43.9%, respectively) Sources: https://pubmed.ncbi.nlm.nih.gov/16093273/ \| https://pubmed.ncbi.nlm.nih.gov/9353355/ \| https://pubmed.ncbi.nlm.nih.gov/10901708/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019810s096lbl.pdf
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf
CYP2C19 1119	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/books/NBK100896/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://www.ncbi.nlm.nih.gov/books/NBK100896/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50275	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50275
MolPort	MolPort-023-330-012	https://www.molport.com/shop/molecule-link/MolPort-023-330-012
ZINC	ZINC000004693574	http://zinc15.docking.org/substances/ZINC000004693574

PubMed

Title	Date	PubMed
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.	2000 Apr	10783826
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.	2000 Oct	11012560
Hypercalcaemia and acute interstitial nephritis associated with omeprazole therapy.	2000 Sep	10978407
Pharmacokinetic study of esomeprazole in the elderly.	2001	11286324
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.	2001	11223960
Antireflux surgery in children suffering from reflux-associated respiratory disease?	2001 Apr	11288221
Pantoprazole and cyclosporine or tacrolimus.	2001 Apr	11284790
Maximal acid reflux control for Barrett's oesophagus: feasible and effective.	2001 Apr	11284781
Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance.	2001 Apr	11284780
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.	2001 Apr 1	11283137
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.	2001 Feb	11281181
Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression.	2001 Feb	11232721
Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy?	2001 Feb	11232676
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.	2001 Feb	11232672
Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer.	2001 Feb	11227677
Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease.	2001 Feb	11220717
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.	2001 Feb	11210394
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.	2001 Feb	11172654
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.	2001 Feb	11167654
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.	2001 Feb	11159802
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.	2001 Feb	11156634
Meta-analysis of randomized controlled trials comparing standard clinical doses of omeprazole and lansoprazole in erosive oesophagitis.	2001 Feb	11148442
Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia.	2001 Feb	11148437
Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection.	2001 Feb 2	11165251
Management of GERD: medical versus surgical.	2001 Jan	11215853
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	11197282
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?	2001 Jan	11157153
Allergic contact dermatitis due to lansoprazole, a proton pump inhibitor.	2001 Jan	11156022
Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer.	2001 Jan	11154169
Switching between intravenous and oral pantoprazole.	2001 Jan	11154164
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.	2001 Jan 15	11212260
Propylene glycol toxicosis in a llama.	2001 Jan 15	11195832
Current approaches to reducing gastrointestinal toxicity of low-dose aspirin.	2001 Jan 8	11166003
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	11166000
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	11208510
Level of malondialdehyde after short-time omeprazole administration.	2001 Jan-Feb	11208500
Effect of polaprezinc on impaired healing of chronic gastric ulcers in adjuvant-induced arthritic rats--role of insulin-like growth factors (IGF)-1.	2001 Jan-Feb	11208487
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals.	2001 Mar	11284340
Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial.	2001 Mar	11280530
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	11240980
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin.	2001 Mar	11240974
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001 Mar	11231401
Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection.	2001 Mar	11207518
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate.	2001 Mar	11207517
One-week ranitidine bismuth citrate-based triple therapy for the eradication of Helicobacter pylori in Hong Kong with high prevalence of metronidazole resistance.	2001 Mar	11207516
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	11207509
Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated.	2001 Mar 6	11242498
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.	2001 Mar 9	11292068
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.	2001 Mar-Apr	11182043

Patents

Sample Use Guides

In Vivo Use Guide

Active Duodenal Ulcer: 20 mg Once daily for 4 weeks. Some patients may require an addition 4 weeks. Gastric Ulcer: oral dose is 40 mg once daily for 4-8 weeks. Gastroesophageal Reflux Disease: The recommended adult oral dose for the treatment of patients with symptomatic GERD and no esophageal lesions is 20 mg daily for up to 4 weeks. The recommended adult oral dose for the treatment of patients with erosive esophagitis and accompanying symptoms due to GERD is 20 mg daily for 4 to 8 weeks.

Route of Administration: Oral

In Vitro Use Guide

Pretreatment of omeprazole (10-6 - 10-4M) dose-dependently inhibits neutrophil adherence and respiratory burst induced by H. pylori. These evidences imply that omeprazole may exhibit a beneficial effect on H. pylori-associated gastric mucosal damage caused by activated neutrophils.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 10:38:37 GMT 2025` Edited by `admin` on `Wed Apr 02 10:38:37 GMT 2025`
Record UNII	ZVL67L3RDK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

3,10-DIMETHOXY-2,4-DIMETHYL-5H-BENZO(4,5)IMIDAZO(1,2-B)PYRIDO(1,2-D)(1,2,4)THIADIAZIN-13-IUM

Systematic Name

English

ESOMEPRAZOLE METABOLITE ACTIVE SULFENAMIDE

Preferred Name

English

OMEPRAZOLE METABOLITE ACTIVE SULFENAMIDE

Common Name

English

Code System Code Type Description

FDA UNII

ZVL67L3RDK

Created by admin on Wed Apr 02 10:38:37 GMT 2025 , Edited by admin on Wed Apr 02 10:38:37 GMT 2025

PRIMARY

PUBCHEM

13553714

Created by admin on Wed Apr 02 10:38:37 GMT 2025 , Edited by admin on Wed Apr 02 10:38:37 GMT 2025

PRIMARY

Related Record Type Details


					ZVL67L3RDK

3,10-DIMETHOXY-2,4-DIMETHYL-5H-BENZO(4,5)IMIDAZO(1,2-B)PYRIDO(1,2-D)(1,2,4)THIADIAZIN-13-IUM

IONIC MOIETY

Amount:


					GAN63K57YG

H+/K+ ATPASE

TARGET -> INHIBITOR

Amount:

Related Record Type Details


					N3PA6559FT

ESOMEPRAZOLE

PRODRUG -> METABOLITE ACTIVE

Amount:


					KG60484QX9

OMEPRAZOLE

PRODRUG -> METABOLITE ACTIVE

Amount:

Related Record Type Details


					ZVL67L3RDK

3,10-DIMETHOXY-2,4-DIMETHYL-5H-BENZO(4,5)IMIDAZO(1,2-B)PYRIDO(1,2-D)(1,2,4)THIADIAZIN-13-IUM

ACTIVE MOIETY

Amount:

AE	Significance	Dose	Population
Headache	3%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/	unhealthy, 45.2 Health Status: unhealthy Age Group: 45.2 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/
Diarrhoea	6%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/	unhealthy, 45.2 Health Status: unhealthy Age Group: 45.2 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/
Nausea	7%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/	unhealthy, 45.2 Health Status: unhealthy Age Group: 45.2 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11563998/
Back pain	1.1%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Cough	1.1%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Asthenia	1.3%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Constipation	1.5%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Dizziness	1.5%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Rash	1.5%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Esophageal acid reflux	1.9%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Upper respiratory infection	1.9%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Flatulence	2.7%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Vomiting	3.2%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Diarrhea	3.7%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Nausea	4%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Abdominal pain	5.2%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf
Headache	6.9%	20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019810s088,022056s003lbl.pdf

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

C_max

T_1/2

Drug as perpetrator