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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42	Primary	Approved 8,429	PRILOSEC
Gastric ulcer 67	Primary	Approved 8,429	PRILOSEC
Gastroesophageal reflux disease 59	Primary	Approved 8,429	PRILOSEC
Pathological hypersecretory conditions 2	Primary	Approved 8,429	PRILOSEC

C_max

Value	Dose	Co-administered	Analyte	Population
668 ng/mL	1 mg/kg single, oral		OMEPRAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
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
1200 nM*h	20 mg single, oral	OMEPRAZOLE 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

Doses

Show entries

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2 n = 161	Other AEs: Nausea, Diarrhoea...
20 mg 1 times / day multiple, oral Recommended	unhealthy n = 3096	Other AEs: Headache, Abdominal pain...

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AEs

Show entries

AE	Significance	Dose	Population
Headache	3%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2 n = 161
Diarrhoea	6%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2 n = 161
Nausea	7%	20 mg 1 times / day multiple, oral Recommended	unhealthy, 45.2 n = 161
Back pain	1.1%	20 mg 1 times / day multiple, oral Recommended	unhealthy n = 3096
Cough	1.1%	20 mg 1 times / day multiple, oral Recommended	unhealthy n = 3096

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 substrate 1,737	inhibitor 1,767 substrate 1,037	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461 CYP2C19 1,478 CYP1A2 1,524 BCRP 699 OATP1B1 788 OAT3 642 OAT1 599 MATE1 306 MATE2 263 OCT2 647 OCT1 512 OCT3 150	P-gp 1,537 CYP2C19 991 CYP2C8 693 CYP2C18 138	MRP3 53 CYP1A1 108 CYP1A2 701 CYP1B1 51

Drug as perpetrator

Show entries

Target	Modality	Activity	Clinical evidence
CYP1A2 1,692	inhibitor 3,277	weak [Ki 150 uM]	weak (co-administration study)
CYP3A4 1,925	inhibitor 3,277	weak [Ki 367.5 uM]
CYP2D6 1,891	inhibitor 3,277	weak [Ki 745.1 uM]
OCT1 543	inhibitor 3,277	yes [IC50 15.7 uM]
BCRP 773	inhibitor 3,277	yes [IC50 17.6 uM]

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Drug as victim

Show entries

Target	Modality	Activity	Clinical evidence
CYP2C19 991	substrate 3,367	major	yes (co-administration study)
CYP3A4 1,737	substrate 3,367	major	yes (co-administration study)
CYP2C18 138	substrate 3,367	minor
CYP2C8 693	substrate 3,367	minor
CYP2C9 1,037	substrate 3,367	minor

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PubMed

Show entries

Title	Date	PubMed
Pharmacokinetic study of esomeprazole in the elderly.	2001	11286324
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
Antireflux surgery in children suffering from reflux-associated respiratory disease?	2001 Apr	11288221
Pantoprazole and cyclosporine or tacrolimus.	2001 Apr	11284790

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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.