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=CC2=C(C=C1)N3SCC4=C(C)C(OC)=C(C)C=[N+]4C3=N2

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: https://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.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heartburn 24 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=477cfda2-44cf-4d0e-bdc4-e30bf16bfea9	Primary		Approved 8429	NEXIUM 24HR Approved Use treats frequent heartburn (occurs 2 or more days a week) Launch Date 2014

C_max

Value	Dose	Co-administered	Analyte	Population
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	Co-administered	Analyte	Population
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
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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 642 CYP2C19 1478 CYP2B6 810 CYP2C8 911 CYP1A2 1524	CYP2C19 991

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 1553	inhibitor 3277 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 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
OAT3 644	inhibitor 3277 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/
MRP1 172	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/30349304/	yes
P-gp 1650	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/33049093/ \| https://pubmed.ncbi.nlm.nih.gov/30349304/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 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 991	substrate 3367 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
[Losec was probably the cause of interstitial nephritis].	1999 Apr 7	10222687
Clarithromycin-induced acute psychoses in peptic ulcer disease.	1999 Jan	10192720
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.	2000 Jul	10859152
Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance.	2001 Apr	11284780
From the Food and Drug Administration.	2001 Apr 4	11277810
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.	2001 Feb	11272330
Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression.	2001 Feb	11232721
Recurrent ulcer bleeding: is intravenous omeprazole the solution?	2001 Feb	11232716
A randomized, pharmacokinetic and pharmacodynamic, cross-over study of duodenal or jejunal administration compared to nasogastric administration of omeprazole suspension in patients at risk for stress ulcers.	2001 Feb	11232677
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
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001 Feb	11227668
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
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
Approach to the patient with unexplained chest pain.	2001 Jan	11216468
Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis.	2001 Jan	11180676
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
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	11136282
[Ulcer therapy with a new proton pump inhibitor. One week of treatment is enough].	2001 Jan 11	11216011
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
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
Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals.	2001 Mar	11284340
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.	2001 Mar	11256484
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
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
Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen.	2001 Mar 29	11274623
[Heartburn. Only a harmless symptom?].	2001 Mar 8	11277116
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
Omeprazole therapy and salivary flow rate in duodenal ulcer patients.	2001 Mar-Apr	11257735
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma.	2001 Mar-Apr	11182042

Patents

Sample Use Guides

In Vivo Use Guide

The drug is administered orally, once daily. The dose depends on the condition treated.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:18:12 GMT 2023` Edited by `admin` on `Sat Dec 16 18:18:12 GMT 2023`
Record UNII	ZVL67L3RDK
Record Status	`Validated (UNII)`
Record Version

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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

OMEPRAZOLE METABOLITE ACTIVE SULFENAMIDE

Common Name

English

ESOMEPRAZOLE METABOLITE ACTIVE SULFENAMIDE

Common Name

English

Code System Code Type Description

FDA UNII

ZVL67L3RDK

Created by admin on Sat Dec 16 18:18:13 GMT 2023 , Edited by admin on Sat Dec 16 18:18:13 GMT 2023

PRIMARY

PUBCHEM

13553714

Created by admin on Sat Dec 16 18:18:13 GMT 2023 , Edited by admin on Sat Dec 16 18:18:13 GMT 2023

PRIMARY

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IONIC MOIETY

Amount:


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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:

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

Approval Year

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

C_max

T_1/2

Drug as perpetrator