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omeprazole 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antiulcer, benzimidazole derivatives	1990	73590-58-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: omeprazole sodium omeprazole omeprazole magnesium omeprazole sodium bicarbonate	A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Molecular weight: 345.42 Formula: C17H19N3O3S CLOGP: 2.56 LIPINSKI: 0 HAC: 6 HDO: 1 TPSA: 77.10 ALOGS: -2.98 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

omeprazole sodium
omeprazole
omeprazole magnesium
omeprazole sodium bicarbonate

A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.

Molecular weight: 345.42
Formula: C17H19N3O3S
CLOGP: 2.56
LIPINSKI: 0
HAC: 6
HDO: 1
TPSA: 77.10
ALOGS: -2.98
ROTB: 5

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
20	mg	O
20	mg	P

ADMET properties:

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Property	Value	Reference
CL (Clearance)	8.40 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	5.79 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	0.58 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	0.50 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K
Vd (Volume of distribution)	0.24 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.05 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.02 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
Sept. 14, 1989	FDA	ASTRAZENECA PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pemphigus	1272.70	10.29	13	464456	183713	62840840
Drug ineffective	1221.60	10.29	3775	460694	1040990	61983563
Contraindicated product administered	1109.30	10.29	142	464327	217506	62807047
Synovitis	1062.14	10.29	80	464389	186838	62837715
Drug intolerance	1038.23	10.29	480	463989	308181	62716372
Hand deformity	1003.24	10.29	37	464432	159420	62865133
Systemic lupus erythematosus	862.72	10.29	231	464238	208687	62815866
Glossodynia	861.66	10.29	138	464331	178738	62845815
Treatment failure	822.01	10.29	220	464249	198823	62825730
Anti-cyclic citrullinated peptide antibody positive	810.35	10.29	7	464462	116205	62908348

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypomagnesaemia	618.62	10.93	856	305210	20995	34629870
Off label use	440.80	10.93	2035	304031	417489	34233376
Drug abuse	422.97	10.93	169	305897	98927	34551938
Drug ineffective	364.10	10.93	2427	303639	454324	34196541
Chronic kidney disease	296.85	10.93	914	305152	40296	34610569
Hypocalcaemia	245.71	10.93	610	305456	23679	34627186
Toxicity to various agents	225.75	10.93	945	305121	199417	34451448
Tubulointerstitial nephritis	203.23	10.93	519	305547	20505	34630360
Hypertrichosis	150.00	10.93	73	305993	340	34650525
Completed suicide	144.88	10.93	412	305654	97756	34553109

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypomagnesaemia	1314.12	10.04	1725	621684	45186	79075793
Drug ineffective	1130.51	10.04	4495	618914	1076418	78044561
Synovitis	892.29	10.04	77	623332	150657	78970322
Drug intolerance	805.08	10.04	538	622871	263581	78857398
Off label use	710.79	10.04	4177	619232	903038	78217941
Pemphigus	682.08	10.04	21	623388	99561	79021418
Hand deformity	658.51	10.04	38	623371	103881	79017098
Treatment failure	635.82	10.04	268	623141	170218	78950761
Tubulointerstitial nephritis	632.65	10.04	1100	622309	37135	79083844
Anti-cyclic citrullinated peptide antibody positive	616.20	10.04	6	623403	83137	79037842

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A02BC01	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Proton pump inhibitors
ATC	A02BD01	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD05	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD16	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
CHEBI has role	CHEBI:35623	anticonvulsants
CHEBI has role	CHEBI:49200	proton pump inhibitors
CHEBI has role	CHEBI:49201	anti-ulcer drugs
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:77746	Homo sapiens metabolite
FDA EPC	N0000175525	Proton Pump Inhibitor

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Peptic ulcer	indication	13200003	DOID:750
Reduction of risk of upper gastrointestinal bleeding	indication	37372002
Erosive esophagitis	indication	40719004
Duodenal ulcer disease	indication	51868009	DOID:1724
Zollinger-Ellison syndrome	indication	53132006	DOID:0050782
Peptic reflux disease	indication	57643001
Gastroesophageal reflux disease	indication	235595009	DOID:8534
Gastric ulcer	indication	397825006	DOID:10808
Duodenal Ulcer due to H. Pylori	indication
Maintenance of Healing Erosive Esophagitis	indication

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🐶 Veterinary Drug Use

Species	Use	Relation
Horses	Gastric ulcers	Indication

🐶 Veterinary products

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Product	Applicant	Ingredients
GastroGard	Boehringer lngelheim Animal Health USA Inc.	1
UlcerGard	Boehringer lngelheim Animal Health USA Inc.	1

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.71	acidic
pKa2	4.44	Basic
pKa3	2.53	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	11135172	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9050263	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9498445	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9603806	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
325MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	6926907	Feb. 28, 2023	TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	8206741	Feb. 28, 2023	TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	9987231	Jan. 2, 2033	FOR SECONDARY PREVENTION OF CARDIOVASCULAR AND CEREBROVASCULAR EVENTS IN PATIENTS AT RISK OF DEVELOPING ASPIRIN-ASSOCIATED GASTRIC ULCERS
325MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	9539214	March 13, 2033	TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	6926907	Feb. 28, 2023	TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS
81MG;40MG	YOSPRALA	GENUS LIFESCIENCES	N205103	Sept. 14, 2016	DISCN	TABLET, DELAYED RELEASE	ORAL	8206741	Feb. 28, 2023	TREATMENT OR SECONDARY PREVENTION OF CARDIOVASCULAR DISEASE, CARDIOVASCULAR EVENTS, OR CEREBROVASCULAR EVENTS AND RISK-REDUCTION OF ASPIRIN-ASSOCIATED GASTRIC ULCERS

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Potassium-transporting ATPase	Transporter	P20648 P51164	ATP4A_HUMAN ATP4B_HUMAN	INHIBITOR	IC50	5.70	CHEMBL	CHEMBL
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	4.05	WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	4.75	CHEMBL
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		Ki	4.35	WOMBAT-PK
Cytochrome P450 1A2	Enzyme	P05177	CP1A2_HUMAN		IC50	4.74	WOMBAT-PK
Cytochrome P450 2C19	Enzyme	P33261	CP2CJ_HUMAN		Ki	5.30	WOMBAT-PK
Fatty acid synthase	Enzyme	P49327	FAS_HUMAN		Ki	5.47	CHEMBL
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Enzyme	O94760	DDAH1_HUMAN		IC50	4.70	CHEMBL
Glutathione S-transferase omega-1	Unclassified	P78417	GSTO1_HUMAN		IC50	5.34	CHEMBL
Cytosolic endo-beta-N-acetylglucosaminidase	Enzyme	Q8NFI3	ENASE_HUMAN		IC50	4.60	CHEMBL

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External reference:

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ID	Source
1C6	PDB_CHEM_ID
003476	NDDF
005065	NDDF
006090	NDDF
174165	MMSL
1792108	RXNORM
25673006	SNOMEDCT_US
34509	MMSL
38031	MMSL
384973006	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Acid Reducer	Human OTC Drug Label	1	0363-1008	TABLET, DELAYED RELEASE	20 mg	ORAL	ANDA	16 sections
Acid Reducer	Human OTC Drug Label	1	0536-1322	TABLET, DELAYED RELEASE	20 mg	ORAL	ANDA	16 sections
Basic Care Omeprazole	HUMAN OTC DRUG LABEL	1	0113-7401	TABLET, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
basic care omeprazole	HUMAN OTC DRUG LABEL	1	0113-7520	TABLET, ORALLY DISINTEGRATING, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
Basic Care Omeprazole	HUMAN OTC DRUG LABEL	1	0113-7915	TABLET, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
good sense omeprazole	HUMAN OTC DRUG LABEL	1	0113-0520	TABLET, ORALLY DISINTEGRATING, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
Good Sense Omeprazole	HUMAN OTC DRUG LABEL	1	0113-0915	TABLET, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
Good Sense Omeprazole	HUMAN OTC DRUG LABEL	1	0113-1723	TABLET, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections
Good Sense Omeprazole and Sodium Bicarbonate	HUMAN OTC DRUG LABEL	2	0113-0058	CAPSULE, GELATIN COATED	20 mg	ORAL	ANDA	15 sections
good sense omeprazole delayed release	HUMAN OTC DRUG LABEL	1	0113-1803	TABLET, DELAYED RELEASE	20 mg	ORAL	NDA	15 sections

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