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
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.	2001	11223960
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?	2001 Apr	11300989
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
Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease.	2001 Feb	11220717
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.	2001 Feb	11167654
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.	2001 Feb	11156634
Leishmania plasma membrane Mg2+-ATPase is a H+/K+-antiporter involved in glucose symport. Studies with sealed ghosts and vesicles of opposite polarity.	2001 Feb 23	11087746
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature.	2001 Jan	11248910
Approach to the patient with unexplained chest pain.	2001 Jan	11216468
Duration of effect of lansoprazole on gastric pH and acid secretion in normal male volunteers.	2001 Jan	11136283
Propylene glycol toxicosis in a llama.	2001 Jan 15	11195832
Current approaches to reducing gastrointestinal toxicity of low-dose aspirin.	2001 Jan 8	11166003
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
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
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
New OTC drugs and devices 2000: a selective review.	2001 Mar-Apr	11297337
Omeprazole therapy and salivary flow rate in duodenal ulcer patients.	2001 Mar-Apr	11257735
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

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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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:


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H+/K+ ATPASE

TARGET -> INHIBITOR

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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