OMEPRAZOLE SODIUM

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H18N3O3S.Na
Molecular Weight	367.398
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].COC1=CC2=C([N-]C(=N2)[S+]([O-])CC3=NC=C(C)C(OC)=C3C)C=C1

InChI

InChIKey=RYXPMWYHEBGTRV-UHFFFAOYSA-N

InChI=1S/C17H18N3O3S.Na/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;/q-1;+1

HIDE SMILES / InChI

Description

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	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Heartburn 24	Primary	Approved 8,583	NEXIUM 24HR
Duodenal ulcer 49	Primary	Approved 8,583	PRILOSEC
Gastric ulcer 74	Primary	Approved 8,583	PRILOSEC
Gastroesophageal reflux disease 68	Primary	Approved 8,583	PRILOSEC
Pathological hypersecretory conditions 9	Primary	Approved 8,583	PRILOSEC

C_max

Value	Dose	Co-administered	Analyte	Population
668 ng/mL	1 mg/kg single, oral		OMEPRAZOLE plasma	Homo sapiens
7.5 μM	40 mg 1 times / day multiple, intravenous		ESOMEPRAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1200 nM*h	20 mg single, oral	OMEPRAZOLE plasma	Homo sapiens
1220 ng × h/mL	1 mg/kg single, oral	OMEPRAZOLE plasma	Homo sapiens
1179 nM × h	20 mg 1 times / day multiple, oral	OMEPRAZOLE plasma	Homo sapiens
16.2 μM × h	40 mg 1 times / day multiple, intravenous	ESOMEPRAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.58 h	20 mg 1 times / day multiple, oral		OMEPRAZOLE plasma	Homo sapiens
1.4 h	40 mg 1 times / day multiple, intravenous		ESOMEPRAZOLE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2	Other AEs: Nausea, Diarrhoea...
20 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Abdominal pain...

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AEs

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AE	Significance	Dose	Population
Headache	3%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2
Diarrhoea	6%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2
Nausea	7%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2
Back pain	1.1%	20 mg 1 times / day multiple, oral Recommended	unhealthy
Cough	1.1%	20 mg 1 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946	inhibitor 2,438 substrate 1,193	inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,741 CYP2C19 2,057 CYP1A2 2,153 BCRP 910 OATP1B1 1,079 OAT3 747 OAT1 725 MATE1 415 MATE2 267 OCT2 779 OCT1 620 OCT3 159 CYP2B6 926 CYP2C8 1,057	P-gp 2,052 CYP2C19 1,119 CYP2C8 810 CYP2C18 149	MRP3 83 CYP1A1 151 CYP1A2 832 CYP1B1 71

Drug as perpetrator

Show entries

Target	Modality	Activity	Clinical evidence
CYP2C19 2,141	inhibitor 4,027	strong [IC50 3.7 uM]	yes (co-administration study)
CYP1A2 2,333	inhibitor 4,027	weak [IC50 >40 uM]
CYP2B6 1,160	inhibitor 4,027	weak [IC50 >40 uM]
CYP2C8 1,117	inhibitor 4,027	weak [IC50 >40 uM]
CYP2C9 2,497	inhibitor 4,027	weak [IC50 >40 uM]

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Drug as victim

Show entries

Target	Modality	Activity	Clinical evidence
CYP2C19 1,119	substrate 4,014	major	yes (co-administration study)
CYP3A4 1,946	substrate 4,014	major	yes (co-administration study)
CYP2C18 149	substrate 4,014	minor
CYP2C8 810	substrate 4,014	minor
CYP2C9 1,193	substrate 4,014	minor

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Reversible renal failure after treatment with omeprazole.	2000 Aug	10924942
Omeprazole-induced delirium.	2000 Jan	10701899
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.	2000 Jul	10859152
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.	2001	11173893
Antireflux surgery in children suffering from reflux-associated respiratory disease?	2001 Apr	11288221

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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.

Show entries

Name

Type

Language

OMEPRAZOLE SODIUM

Official Name

English

LOSEC SODIUM

Preferred Name

English

1H-BENZIMIDAZOLE, 5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, SODIUM SALT

Common Name

English

OMEPRAZOLE SODIUM [EP MONOGRAPH]

Common Name

English

OMEPRAZOLE SODIUM [MART.]

Common Name

English

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Classification Tree

Code System

Code

Anti-ulcer Agent

NCI_THESAURUS

C29723

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Show entries

Code System

Code

Type

Description

CAS

95510-70-6

PRIMARY

NCI_THESAURUS

C74598

PRIMARY

PUBCHEM

10959536

PRIMARY

USAN

DD-47

PRIMARY

EPA CompTox

DTXSID10635761

PRIMARY

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ACTIVE MOIETY


					KG60484QX9

OMEPRAZOLE

SUBSTANCE RECORD


					KV03YZ6QLW

OMEPRAZOLE SODIUM

SMILES

InChI

CNS Activity

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator