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

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 31 Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411559	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8429	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 67 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8429	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 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8429	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 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022056lbl.pdf	Primary	Approved 8429	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

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 1587 substrate 1737	inhibitor 1767 substrate 1037	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP2C19 1478 CYP1A2 1524 BCRP 699 OATP1B1 788 OAT3 642 OAT1 599 MATE1 306 MATE2 263 OCT2 647 OCT1 512 OCT3 150	P-gp 1537 CYP2C19 991 CYP2C8 693 CYP2C18 138	MRP3 53 CYP1A1 108 CYP1A2 701 CYP1B1 51

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 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 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	weak [Ki 367.5 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	weak [Ki 745.1 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 15.7 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19076159/	yes [IC50 17.6 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	yes [IC50 17.7 uM]
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 22 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 4.32 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://pubmed.ncbi.nlm.nih.gov/21779389/	yes [IC50 6.7 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25239859/	yes [IC50 6.8 uM]
OATP1B1 803	inhibitor 3277 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 1553	inhibitor 3277 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 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/10445394/	yes
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP1B1 67	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/	yes
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/ \| https://pubmed.ncbi.nlm.nih.gov/16248835/	yes
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/20053795/ \| https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MATE2 263	inhibitor 3277 Sources: https://faseb.onlinelibrary.wiley.com/doi/abs/10.1096/fasebj.2020.34.s1.09069	yes
MRP3 207	inducer 1573 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 991	substrate 3367 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 1737	substrate 3367 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 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8894508/	minor
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11770010/	no

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
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.	2001	11223960
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001 Apr	11266411
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.	2001 Apr 1	11283137
From the Food and Drug Administration.	2001 Apr 4	11277810
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
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
Aggressive acid control: minimizing progression of Barrett's esophagus.	2001 Feb	11225348
[A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment].	2001 Feb	11218406
[Usefulness of new triple therapy containing PPI].	2001 Feb	11218404
[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
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
Management of GERD: medical versus surgical.	2001 Jan	11215853
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.	2001 Jan	11136281
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.	2001 Jan 15	11212260
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.	2001 Jan 5	11137875
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
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
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
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
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
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
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.

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