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Human Metabolome Database Version 3.5

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Showing metabocard for Pantoprazole (HMDB05017)

Record Information
Version 3.5
Creation Date 2006-10-17 02:47:22 -0600
Update Date 2013-02-08 17:13:46 -0700
HMDB ID HMDB05017
Secondary Accession Numbers None
Metabolite Identification
Common Name Pantoprazole
Description Pantozol; 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Pantoloc
  2. Pantoprazole sodium
  3. Pantoprazole Sodium Hydrate
  4. Pantozol
  5. Protonix
  6. Protonix I.V.
Chemical Formula C16H15F2N3O4S
Average Molecular Weight 383.37
Monoisotopic Molecular Weight 383.075133083
IUPAC Name 6-(difluoromethoxy)-2-{[(3,4-dimethoxypyridin-2-yl)methane]sulfinyl}-1H-1,3-benzodiazole
Traditional IUPAC Name 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole
CAS Registry Number 102625-70-7
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 Key IQPSEEYGBUAQFF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzimidazoles
Sub Class Sulfinylbenzimidazoles
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • benzimidazoles(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Imidazole
  • Organic Halide
  • Organofluoride
  • Orthocarboxylic Acid Derivative
  • Pyridine
  • Sulfoxide
Direct Parent Sulfinylbenzimidazoles
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.49 g/L ALOGPS
LogP 2.11 ALOGPS
LogP 2.18 ChemAxon
LogS -2.89 ALOGPS
pKa (strongest acidic) 9.15 ChemAxon
pKa (strongest basic) 3.55 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 86.33 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 90.05 ChemAxon
Polarizability 35.03 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
10.0 +/- 0.002 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023589
KNApSAcK ID Not Available
Chemspider ID 4517 Link_out
KEGG Compound ID C11806 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Pantoprazole Link_out
NuGOwiki Link HMDB05017 Link_out
Metagene Link HMDB05017 Link_out
METLIN ID 1697 Link_out
PubChem Compound 4679 Link_out
PDB ID Not Available
ChEBI ID 7915 Link_out
References
Synthesis Reference Kohl, 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 References Not Available
Enzymes
Name: Cytochrome P450 3A4
Reactions:
  • (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
  • (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions:
  • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Potassium-transporting ATPase alpha chain 2
Reactions:
  • ATP + H2O + H+in + K+out = ADP + phosphate + H+out + K+in [RN:R00086]
Gene Name: ATP12A
Uniprot ID: P54707 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sodium/potassium-transporting ATPase subunit alpha-1
Reactions:
  • ATP + H2O + Na+in + K+out = ADP + phosphate + Na+out + K+in [RN:R00086]
Gene Name: ATP1A1
Uniprot ID: P05023 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Potassium-transporting ATPase alpha chain 1
Reactions:
  • ATP + H2O + H+in + K+out = ADP + phosphate + H+out + K+in [RN:R00086]
Gene Name: ATP4A
Uniprot ID: P20648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA