OMEPRAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H19N3O3S
Molecular Weight	345.416
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(NC(=N2)[S+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1

InChI

InChIKey=SUBDBMMJDZJVOS-UHFFFAOYSA-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)

HIDE SMILES / InChI

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

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

Omeprazole belongs to a class of antisecretory compounds, which suppress gastric acid secretion by specific inhibition of the H+ /K+ ATPase enzyme system at the secretory surface of the gastric parietal cell. Because this enzyme system is regarded as the acid (proton) pump within the gastric mucosa, omeprazole has been characterized as a gastric acid-pump inhibitor, in that it blocks the final step of acid production. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus. Omeprazole is used under brand names Prilosec and Losec for treatment of duodenal ulcer in adults, gastric ulcer in adults, Gastroesophageal Reflux Disease. In addition it used for maintenance of healing of erosive esophagitis in pediatric patients and adults and for treatment of pathological hypersecretory conditions in adults (eg, Zollinger-Ellison syndrome, multiple endocrine adenomas and systemic mastocytosis). The most frequent significant adverse effects occurring in at least of patients include headache; upper respiratory tract infection, abdominal pain, diarrhea, back pain, weakness and rash.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 30 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411559	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8307	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 1.20597119E12
Gastric ulcer 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8307	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 1.20597119E12
Gastroesophageal reflux disease 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8307	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 6.217344E11
Pathological hypersecretory conditions 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8307	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 1.20597119E12

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

AUC

Value	Dose	Analyte	Population
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
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:

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

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 n = 161 Health Status: unhealthy Condition: reflux oesophagitis Age Group: 45.2 Sex: M+F Population Size: 161 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 n = 3096 Health Status: unhealthy Condition: Duodenal ulcer \| Resistant ulcer \| Zollinger-Ellison syndrome Population Size: 3096 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 1532 substrate 1670	inhibitor 1695 substrate 985	inhibitor 1789

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1401 CYP2C19 1410 CYP1A2 1463 BCRP 678 OATP1B1 770 OAT3 625 OAT1 584 MATE1 302 MATE2 259 OCT2 630 OCT1 498 OCT3 143	P-gp 1491 CYP2C19 955 CYP2C8 670 CYP2C18 138	MRP3 53 CYP1A1 103 CYP1A2 671 CYP1B1 50

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1620	inhibitor 3185 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 1857	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	weak [Ki 367.5 uM]
CYP2D6 1826	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	weak [Ki 745.1 uM]
OCT1 513	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 15.7 uM]
BCRP 751	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/19076159/	yes [IC50 17.6 uM]
P-gp 1588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	yes [IC50 17.7 uM]
OCT3 143	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 22 uM]
OAT1 588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 4.32 uM]
OCT2 631	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 6.7 uM]
OAT3 627	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 6.8 uM]
OATP1B1 785	inhibitor 3185 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 1484	inhibitor 3185 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 206	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/10445394/	yes
CYP1A2 1620	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP1B1 66	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP2C9 1747	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	yes
MATE1 304	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MATE2 259	inhibitor 3185 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MRP3 206	inducer 1515 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 955	substrate 3264 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 1670	substrate 3264 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 138	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C8 670	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C9 985	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	no

PubMed

Title	Date	PubMed
Clarithromycin-induced acute psychoses in peptic ulcer disease.	1999 Jan	10192720
Omeprazole-induced delirium.	2000 Jan	10701899
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.	2000 Mar	10750652
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.	2000 Oct	11012560
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.	2001	11178116
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?	2001 Apr	11300989
Pantoprazole and cyclosporine or tacrolimus.	2001 Apr	11284790
A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer.	2001 Apr	11266390
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.	2001 Feb	11293500
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.	2001 Feb	11272330
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001 Feb	11227668
[Selection of antibiotics and planning of eradication for H. pylori infection].	2001 Feb	11218403
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.	2001 Feb	11172654
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.	2001 Feb	11159802
Meta-analysis of randomized controlled trials comparing standard clinical doses of omeprazole and lansoprazole in erosive oesophagitis.	2001 Feb	11148442
The prescribing of acid suppressants prior to the endoscopic diagnosis of Barrett's oesophagus and oesophagitis.	2001 Feb	11148441
Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia.	2001 Feb	11148437
The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy.	2001 Feb	11148433
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
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies.	2001 Jan	11197288
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
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
Accuracy of the stool antigen test in the diagnosis of Helicobacter pylori infection before treatment and in patients on omeprazole therapy.	2001 Jan	11136280
Propylene glycol toxicosis in a llama.	2001 Jan 15	11195832
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.	2001 Jan 5	11137875
Level of malondialdehyde after short-time omeprazole administration.	2001 Jan-Feb	11208500
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
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
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
[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
New OTC drugs and devices 2000: a selective review.	2001 Mar-Apr	11297337
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

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 `Fri Dec 16 22:45:15 UTC 2022` Edited by `admin` on `Fri Dec 16 22:45:15 UTC 2022`
Record UNII	KG60484QX9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OMEPRAZOLE

Official Name

English

OMEPRAZOLE [JAN]

Common Name

English

OMEPRAZOLE COMPONENT OF ZEGERID

Common Name

English

5-METHOXY-2-(((4-METHOXY-3,5,-DIMETHYL-2-PYRIDINYL)-METHYL)SULPHINYL)-1H-BENZIMIDAZOLE

Common Name

English

NSC-759192

Code

English

NSC-751450

Code

English

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

Systematic Name

English

OMEPRAZOLE COMPONENT OF YOSPRALA

Brand Name

English

OMEPRAZOLE [USP-RS]

Common Name

English

OMEPRAZOLE [USP MONOGRAPH]

Common Name

English

OMEPRAZOLE [HSDB]

Common Name

English

OMEPRAZOLE [MART.]

Common Name

English

OMEPRAZOLE [USP IMPURITY]

Common Name

English

LOSEC

Brand Name

English

H-168/68

Code

English

5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]benzimidazole

Systematic Name

English

OMEPRAZOLE [MI]

Common Name

English

OMEPRAZOLE [GREEN BOOK]

Common Name

English

ZEGERID COMPONENT OMEPRAZOLE

Common Name

English

(RS)-6-METHOXY-2-((4-METHOXY-3,5-DIMETHYLPYRIDIN-2-YL) METHYLSULFINYL)-1H-BENZO(D)IMIDAZOLE

Systematic Name

English

omeprazole [INN]

Common Name

English

H 168/68

Code

English

Omeprazole [WHO-DD]

Common Name

English

OMEPRAZOLE [VANDF]

Common Name

English

OMEPRAZOLE [ORANGE BOOK]

Common Name

English

OMEPRAZOLE [USAN]

Common Name

English

YOSPRALA COMPONENT OMEPRAZOLE

Brand Name

English

Classification Tree Code System Code

WHO-ATC

A02BD05