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Showing drug card for Omeprazole (DB00338)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:28
Primary Accession Number DB00338
Secondary Accession Number
  • APRD00446
Name Omeprazole
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]
Synonyms
  1. OMEP
  2. OMP
  3. OMZ
  4. Omeprazol [INN-Spanish]
  5. Omeprazole magnesium
  6. Omeprazolum [INN-Latin]
  7. omeprazole
Brand Names
  1. Antra
  2. Audazol
  3. Aulcer
  4. Belmazol
  5. Ceprandal
  6. Danlox
  7. Demeprazol
  8. Desec
  9. Dizprazol
  10. Dudencer
  11. Elgam
  12. Emeproton
  13. Epirazole
  14. Erbolin
  15. Exter
  16. Gasec
  17. Gastrimut
  18. Gastroloc
  19. Gibancer
  20. Indurgan
  21. Inhibitron
  22. Inhipump
  23. Lensor
  24. Logastric
  25. Lomac
  26. Losec
  27. Mepral
  28. Miol
  29. Miracid
  30. Mopral
  31. Morecon
  32. Nilsec
  33. Nopramin
  34. Ocid
  35. Olexin
  36. Omapren
  37. Omebeta 20
  38. Omed
  39. Omegast
  40. Omepral
  41. Omeprazon
  42. Omeprol
  43. Omesek
  44. Omezol
  45. Omezolan
  46. Omid
  47. Omisec
  48. Omizac
  49. Ompanyt
  50. Ortanol
  51. Osiren
  52. Ozoken
  53. Paprazol
  54. Parizac
  55. Pepticum
  56. Pepticus
  57. Peptilcer
  58. Prazentol
  59. Prazidec
  60. Prazolit
  61. Prilosec
  62. Procelac
  63. Proclor
  64. Prysma
  65. Ramezol
  66. Regulacid
  67. Result
  68. Sanamidol
  69. Secrepina
  70. Tedec Ulceral
  71. Ulceral
  72. Ulcesep
  73. Ulcometion
  74. Ulcozol
  75. Ulcsep
  76. Ulsen
  77. Ultop
  78. Ulzol
  79. Victrix
  80. Zefxon
  81. Zegerid
  82. Zepral
  83. Zimor
  84. Zoltum
Brand Mixtures Not Available
Chemical IUPAC Name 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
Chemical Formula C17H19N3O3S
Chemical Structure Structure
CAS Registry Number 73590-58-6
InChI Identifier InChI=1/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)/f/h20H
InChI Key SUBDBMMJDZJVOS-UYBDAZJACN
KEGG Drug D00455 Link Image
KEGG Compound C07324 Link Image
PubChem Compound 4594 Link Image
PubChem Substance 189970 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02260867 Link Image
RxList Link http://www.rxlist.com/cgi/generic/omepra.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pri1350.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Omeprazole Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference U. K. Junggren, S. E. Sjostrand, U.S. Pat. 4,255,431 (1979)
Average Molecular Weight 345.4160
Monoisotopic Molecular Weight 345.1147
State Solid
Melting Point 156 oC
Experimental Water Solubility 82.3 mg/L Source: PhysProp
Predicted Water Solubility 3.59e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.6 Source: PhysProp
Predicted LogP 1.91 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.98 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES COC1=CC2=C(C=C1)N=C(N2)[S@@](=O)CC1=NC=C(C)C(OC)=C1C
Canonical SMILES COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C
Drug Category
  • Anti-Ulcer Agents
  • Enzyme Inhibitors
  • Proton-pump Inhibitors
ATC Codes
AHFS Codes
  • 56:28.36
Indication For the treatment of gastroesophageal reflux disease.
Pharmacology Omeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Omeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that 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.
Mechanism of Action Omeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, omeprazole blocks the final step in acid production, thus reducing gastric acidity.
Absorption Absorption is rapid, absolute bioavailability (compared to intravenous administration) is about 30-40% at doses of 20-40 mg.
Toxicity Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Protein Binding 95%
Biotransformation Hepatic.
Half Life 0.5-1 hour
Dosage Forms
Form Route
Capsule Oral
Capsule, delayed release Oral
Tablet, delayed release Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Alprazolam Omeprazole increases the effect of benzodiazepine
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Chlordiazepoxide Omeprazole increases the effect of benzodiazepine
Cilostazol Omeprazole increases the effect of cilostazol
Clonazepam Omeprazole increases the effect of benzodiazepine
Clorazepate Omeprazole increases the effect of benzodiazepine
Cyclosporine Omeprazole increases the effect and toxicity of cyclosporine
Dasatinib Possible decreased levels of dasatinib
Diazepam Omeprazole increases the effect of benzodiazepine
Disopyramide The beta-blocker increases toxicity of disopyramide
Enoxacin The agent decreases the absorption of enoxacin
Estazolam Omeprazole increases the effect of benzodiazepine
Ethotoin Omeprazole increases the effect of hydantoin
Flurazepam Omeprazole increases the effect of benzodiazepine
Fosphenytoin Omeprazole increases the effect of hydantoin
Halazepam Omeprazole increases the effect of benzodiazepine
Indinavir Omeprazole decreases the absorption of indinavir
Itraconazole The proton pump inhibitor decreases the absorption of the imidazole
Ketazolam Omeprazole increases the effect of benzodiazepine
Ketoconazole The proton pump inhibitor decreases the absorption of the imidazole
Mephenytoin Omeprazole increases the effect of hydantoin
Methotrexate Omeprazole increases the levels of methotrexate
Midazolam Omeprazole increases the effect of benzodiazepine
Phenytoin Omeprazole increases the effect of hydantoin
Prazepam Omeprazole increases the effect of benzodiazepine
Quazepam Omeprazole increases the effect of benzodiazepine
St. John's Wort St. John's Wort decreases the levels/effects of omeprazole
Triazolam Omeprazole increases the effect of benzodiazepine
Voriconazole Voriconazole increases the effect and toxicity of omeprazole
Food Interactions
  • Avoid alcohol.
  • Take 30-60 minutes before meals.
Pathways
Name SMPDB Link KEGG Link
Omeprazole Pathway SMP00226 Link Image
General References
  1. Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. [PubMed Link Image]
  2. Drugs.com Link Image
  3. Wikipedia Link Image
  4. RxList Link Image
  5. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
Targets
  1. Potassium-transporting ATPase alpha chain 1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 385
Target 1 Name Potassium-transporting ATPase alpha chain 1
Target 1 Synonyms
  1. EC 3.6.3.10
  2. Gastric H(+)/K(+) ATPase subunit alpha
  3. Proton pump
Target 1 Gene Name ATP4A
Target 1 Protein Sequence >Potassium-transporting ATPase alpha chain 1 
GKAENYELYSVELGPGPGGDMAAKMSKKKKAGGGGGKRKEKLENMKKEMEINDHQLSVAE
LEQKYQTSATKGLSASLAAELLLRDGPNALRPPRGTPEYVKFARQLAGGLQCLMWVAAAI
CLIAFAIQASEGDLTTDDNLYLAIALIAVVVVTGCFGYYQEFKSTNIIASFKNLVPQQAT
VIRDGDKFQINADQLVVGDLVEMKGGDRVPADIRILAAQGCKVDNSSLTGESEPQTRSPE
CTHESPLETRNIAFFSTMCLEGTAQGLVVNTGDRTIIGRIASLASGVENEKTPIAIEIEH
FVDIIAGLAILFGATFFIVAMCIGYTFLRAMVFFMAIVVAYVPEGLLATVTVCLSLTAKR
LASKNCVVKNLEAVETLGSTSVICSDKTGTLTQNRMTVSHLWFDNHIHTADTTEDQSGQT
FDQSSETWRALCRVLTLCNRAAFKSGQDAVPVPKRIVIGDASETALLKFSELTLGNAMGY
RDRFPKVCEIPFNSTNKFQLSIHTLEDPRDPRHLLVMKGAPERVLERCSSILIKGQELPL
DEQWREAFQTAYLSLGGLGERVLGFCQLYLNEKDYPPGYAFDVEAMNFPSSGLCFAGLVS
MIDPPRATVPDAVLKCRTAGIRVIMVTGDHPITAKAIAASVGIISEGSETVEDIAARLRV
PVDQVNRKDARACVINGMQLKDMDPSELVEALRTHPEMVFARTSPQQKLVIVESCQRLGA
IVAVTGDGVNDSPALKKADIGVAMGIAGSDAAKNAADMILLDDNFASIVTGVEQGRLIFD
NLKKSIAYTLTKNIPELTPYLIYITVSVPLPLGCITILFIELCTDIFPSVSLAYEKAESD
IMHLRPRNPKRDRLVNEPLAAYSYFQIGAIQSFAGFTDYFTAMAQEGWFPLLCVGLRAQW
EDHHLQDLQDSYGQEWTFGQRLYQQYTCYTVFFISIEVCQIADVLIRKTRRLSAFQQGFF
RNKILVIAIVFQVCIGCFLCYCPGMPNIFNFMPIRFQWWLVPLPYGILIFVYDEIRKLGV
RCCPGSWWDQELYY
Target 1 Number of Residues 1051
Target 1 Molecular Weight 113961
Target 1 Theoretical pI 5.54
Target 1 GO Classification
Function
hydrolase activity
hydrolase activity, acting on acid anhydrides
hydrolase activity, acting on acid anhydrides, catalyzing transmembrane movement of substances
catalytic activity
binding
nucleotide binding
purine nucleotide binding
adenyl nucleotide binding
ATP binding
monovalent inorganic cation transporter activity
transporter activity
ion transporter activity
cation transporter activity
ATPase activity, coupled to transmembrane movement of ions, phosphorylative mechanism
Process
metabolism
monovalent inorganic cation transport
physiological process
cellular physiological process
transport
ion transport
cation transport
Component
intrinsic to membrane
integral to membrane
cell
membrane
Target 1 General Function Inorganic ion transport and metabolism
Target 1 Specific Function Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach
Target 1 Pathways
Name SMPDB Link KEGG Link
Oxidative phosphorylation map00190 Link Image
Target 1 Reactions
  • ATP + H2O + H+in + K+out = ADP + phosphate + H+out + K+in
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 98-118
  • 142-162
  • 299-318
  • 331-348
  • 783-802
  • 813-833
  • 854-876
  • 929-948
  • 963-981
  • 997-1017
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 561634 Link Image
Target 1 UniProtKB/Swiss-Prot ID P20648 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ATP4A_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >3108 bp 
ATGGGGAAGGCCGAGAACTATGAGCTCTACTCGGTGGAGCTGGGTCCTGGCCCTGGCGGG
GACATGGCTGCCAAGATGAGCAAGAAGAAGAAGGCGGGTGGCGGGGGTGGCAAGAGGAAG
GAGAAGCTGGAGAACATGAAGAAGGAGATGGAGATTAACGACCACCAGCTGTCAGTGGCG
GAGCTGGAACAGAAATACCAGACCAGTGCCACCAAGGGCCTCTCTGCGAGCCTGGCTGCT
GAGCTGCTGCTGCGGGATGGGCCCAACGCACTGCGGCCACCACGGGGCACCCCAGAGTAC
GTCAAGTTCGCGAGGCAGCTGGCCGGGGGCCTGCAGTGCCTCATGTGGGTTGCCGCCGCC
ATCTGCCTCATCGCCTTTGCCATCCAGGCTAGTGAGGGGGACCTCACCACCGACGACAAT
CTGTACCTGGCAATCGCTCTCATTGCTGTGGTTGTCGTCACCGGCTGCTTTGGCTACTAC
CAGGAATTCAAGAGCACCAACATCATCGCCAGCTTTAAGAACCTTGTGCCACAGCAAGCC
ACTGTCATCCGCGATGGAGACAAATTCCAGATCAACGCTGACCAACTGGTGGTGGGCGAC
CTGGTGGAGATGAAAGGTGGGGACAGAGTGCCCGCCGACATCCGCATCCTGGCGGCCCAG
GGCTGCAAGGTGGACAACTCCTCGCTGACAGGGGAGTCTGAGCCACAGACCCGCTCACCC
GAGTGCACGCACGAGAGCCCTCTGGAGACCCGCAACATCGCCTTCTTCTCCACCATGTGC
CTTGAGGGCACCGCGCAGGGCCTGGTGGTGAACACGGGCGACCGCACCATCATTGGGCGC
ATCGCATCGCTGGCGTCGGGGGTGGAAAACGAGAAGACACCCATCGCTATCGAGATCGAG
CATTTTGTGGACATCATCGCGGGCCTGGCCATTCTCTTCGGTGCCACATTTTTTATTGTG
GCCATGTGCATTGGCTACACCTTCCTGCGGGCCATGGTCTTCTTCATGGCCATCGTGGTG
GCCTATGTGCCTGAGGGGCTGCTGGCCACTGTCACAGTCTGCCTGTCCCTGACAGCCAAG
CGCCTGGCCAGTAAGAACTGCGTGGTCAAGAACCTGGAGGCGGTGGAGACATTGGGCTCC
ACTTCGGTGATCTGCTCGGACAAGACAGGGACTCTCACTCAGAACCGCATGACTGTGTCC
CATCTTTGGTTTGACAACCACATCCACACAGCTGACACCACGGAAGACCAGTCAGGGCAG
ACGTTTGACCAGTCCTCGGAGACGTGGCGGGCGCTGTGCCGGGTGCTCACCCTGTGCAAC
CGCGCCGCCTTCAAGTCCGGCCAGGATGCAGTGCCTGTGCCCAAGCGCATCGTGATTGGA
GACGCATCGGAGACGGCGCTGCTCAAGTTCTCGGAGCTGACGCTGGGCAACGCCATGGGC
TACCGGGACCGCTTCCCAAAAGTCTGCGAGATACCCTTCAACTCCACCAACAAGTTCCAG
CTGTCCATACATACGCTGGAGGACCCGCGGGACCCGCGACACTTGCTGGTGATGAAGGGC
GCCCCCGAGCGCGTGCTGGAGCGCTGCAGCTCCATCCTTATCAAGGGCCAGGAGCTGCCG
CTGGACGAGCAGTGGCGCGAGGCCTTCCAGACCGCCTACCTCAGCCTGGGAGGCCTGGGC
GAACGCGTGCTCGGCTTCTGCCAGCTCTACCTGAATGAGAAGGACTACCCGCCTGGCTAT
GCCTTCGACGTAGAGGCCATGAACTTTCCATCTAGCGGCCTCTGCTTTGCGGGACTTGTA
TCCATGATTGACCCACCCCGGGCCACCGTCCCTGATGCTGTGCTCAAGTGTCGCACCGCA
GGCATCCGGGTGATCATGGTAACGGGTGACCACCCCATCACCGCCAAGGCCATTGCAGCC
AGTGTGGGCATCATCTCGGAAGGCAGCGAGACAGTGGAGGACATCGCTGCCCGCCTCCGT
GTGCCCGTAGACCAGGTTAATCGCAAGGATGCCCGTGCCTGTGTGATCAATGGCATGCAG
CTGAAGGACATGGACCCATCGGAACTGGTCGAGGCCCTGCGCACCCACCCCGAGATGGTG
TTTGCGCGCACCAGCCCCCAGCAGAAGCTGGTGATCGTGGAGAGCTGCCAGCGGCTGGGT
GCGATTGTGGCCGTCACGGGGGATGGTGTGAATGACTCCCCAGCTCTGAAGAAGGCAGAC
ATCGGAGTAGCCATGGGCATCGCTGGCTCAGATGCTGCCAAAAATGCAGCTGACATGATC
CTGCTGGATGACAACTTTGCCTCCATTGTGACAGGCGTGGAGCAGGGTCGACTGATCTTC
GACAACCTGAAGAAGTCTATTGCCTACACATTGACCAAGAACATCCCAGAGCTGACACCC
TACCTCATCTACATCACCGTCAGCGTGCCCCTGCCCCTCGGGTGCATCACCATCCTCTTC
ATCGAACTCTGCACTGACATTTTCCCATCTGTGTCCCTGGCATATGAAAAGGCCGAGAGT
GACATCATGCACCTGCGTCCACGCAACCCAAAGCGTGACAGATTGGTCAACGAGCCCCTG
GCTGCCTACTCCTACTTCCAGATTGGTGCCATTCAGTCCTTTGCTGGCTTCACTGACTAC
TTCACGGCAATGGCCCAGGAGGGCTGGTTCCCACTGCTGTGCGTGGGGCTGCGGGCGCAG
TGGGAGGACCACCACCTACAAGATCTGCAGGACAGCTACGGCCAGGAGTGGACATTCGGG
CAGCGCCTGTACCAGCAGTACACCTGCTACACCGTGTTCTTCATCAGCATTGAGGTGTGC
CAGATCGCCGATGTCCTCATCCGCAAGACGCGCCGTCTCTCTGCCTTCCAGCAAGGCTTC
TTCAGGAATAAGATCCTGGTGATCGCCATCGTGTTCCAGGTCTGCATCGGCTGCTTCCTG
TGCTACTGCCCCGGCATGCCCAACATCTTCAACTTCATGCCCATTCGGTTCCAGTGGTGG
CTGGTCCCCCTGCCCTACGGCATCCTCATCTTCGTCTATGATGAGATCCGGAAGCTTGGA
GTTCGCTGTTGCCCAGGGAGCTGGTGGGACCAGGAACTCTACTATTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID ATP4A Link Image
Target 1 GenAtlas ID ATP4A Link Image
Target 1 HGNC ID HGNC:819 Link Image
Target 1 Chromosome Location 19
Target 1 Locus 19q13.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Maeda M, Oshiman K, Tamura S, Futai M: Human gastric (H+ + K+)-ATPase gene. Similarity to (Na+ + K+)-ATPase genes in exon/intron organization but difference in control region. J Biol Chem. 1990 Jun 5;265(16):9027-32. [PubMed Link Image]
  2. Newman PR, Greeb J, Keeton TP, Reyes AA, Shull GE: Structure of the human gastric H,K-ATPase gene and comparison of the 5'-flanking sequences of the human and rat genes. DNA Cell Biol. 1990 Dec;9(10):749-62. [PubMed Link Image]
  3. Sverdlov ED, Monastyrskaya GS, Broude NE, Ushkaryov YuA, Allikmets RL, Melkov AM, Smirnov YuV, Malyshev IV, Dulobova IE, Petrukhin KE, et al.: The family of human Na+,K+-ATPase genes. No less than five genes and/or pseudogenes related to the alpha-subunit. FEBS Lett. 1987 Jun 15;217(2):275-8. [PubMed Link Image]
Target 1 Drug References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]

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