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Record Information
Version3.6
Creation Date2006-10-17 08:47:22 UTC
Update Date2013-02-09 00:13:46 UTC
HMDB IDHMDB05017
Secondary Accession NumbersNone
Metabolite Identification
Common NamePantoprazole
DescriptionPantozol; Pantoprazole (brand names Pantopan in Italy; Protium; Protonix; Pantozol; Pantor; Pantoloc) is a proton pump inhibitor drug used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease. Initial treatment is generally of eight weeks' duration, after which another eight week course of treatment may be considered if necessary. It can be used as a maintenance therapy for long term use after initial response is obtained; Pantoprazole is a proton pump inhibitor drug used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease. Initial treatment is generally of eight weeks' duration, after which another eight week course of treatment may be considered if necessary. It can be used as a maintenance therapy for long term use after initial response is obtained. Pantoprazole is metabolized in the liver by the cytochrome P450 system. Metabolism mainly consists of demethylation by CYP2C19 followed by sulfation. Another metabolic pathway is oxidation by CYP3A4. Pantoprazole metabolites are not thought to have any pharmacological significance; Protium; Pantor; Pantoloc) is a proton pump inhibitor drug used for short-term treatment of erosion and ulceration of the esophagus caused by gastroesophageal reflux disease. Initial treatment is generally of eight weeks' duration, after which another eight week course of treatment may be considered if necessary. It can be used as a maintenance therapy for long term use after initial response is obtained; Protonix; Pantoprazole (brand names Pantopan in Italy.
Structure
Thumb
Synonyms
  1. Pantoloc
  2. Pantoprazole sodium
  3. Pantoprazole Sodium Hydrate
  4. Pantozol
  5. Protonix
  6. Protonix I.V.
Chemical FormulaC16H15F2N3O4S
Average Molecular Weight383.37
Monoisotopic Molecular Weight383.075133083
IUPAC Name6-(difluoromethoxy)-2-{[(3,4-dimethoxypyridin-2-yl)methane]sulfinyl}-1H-1,3-benzodiazole
Traditional Name5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole
CAS Registry Number102625-70-7
SMILES
COC1=C(OC)C(CS(=O)C2=NC3=C(N2)C=C(OC(F)F)C=C3)=NC=C1
InChI Identifier
InChI=1S/C16H15F2N3O4S/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16/h3-7,15H,8H2,1-2H3,(H,20,21)
InChI KeyIQPSEEYGBUAQFF-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzimidazoles
Sub ClassSulfinylbenzimidazoles
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • benzimidazoles(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Imidazole
  • Organic Halide
  • Organofluoride
  • Orthocarboxylic Acid Derivative
  • Pyridine
  • Sulfoxide
Direct ParentSulfinylbenzimidazoles
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.49ALOGPS
logP2.11ALOGPS
logP2.18ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)3.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.33 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.05 m3·mol-1ChemAxon
Polarizability35.03 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 +/- 0.002 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023589
KNApSAcK IDNot Available
Chemspider ID4517
KEGG Compound IDC11806
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPantoprazole
NuGOwiki LinkHMDB05017
Metagene LinkHMDB05017
METLIN ID1697
PubChem Compound4679
PDB IDNot Available
ChEBI ID7915
References
Synthesis ReferenceKohl, Bernhard; Sturm, Ernst; Klemm, Kurt; Riedel, Richard; Figala, Volker; Rainer, Georg; Schaefer, Hartmann; Senn-Bilfinger, Joerg. [[(Dialkoxypyridyl)methyl]thio]benzimidazoles. Eur. Pat. Appl. (1986), 64 pp. CODEN: EPXXDW EP 166287 A1 19860102 CAN 105:6506 AN 1986:406506
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in ATP binding
Specific function:
Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for potassium absorption in various tissues.
Gene Name:
ATP12A
Uniprot ID:
P54707
Molecular weight:
116052.03
General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
General function:
Involved in ATP binding
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.
Gene Name:
ATP4A
Uniprot ID:
P20648
Molecular weight:
114117.74
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915