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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:34:03 UTC
HMDB IDHMDB15695
Secondary Accession NumbersNone
Metabolite Identification
Common NameRoxatidine acetate
DescriptionRoxatidine acetate is only found in individuals that have used or taken this drug. It is a specific and competitive H2 receptor antagonist. It is currently approved in South Africa under the tradename Roxit.The H2 antagonists are competitive inhibitors of histamine at the parietal cell H2 receptor. They suppress the normal secretion of acid by parietal cells and the meal-stimulated secretion of acid. They accomplish this by two mechanisms: histamine released by ECL cells in the stomach is blocked from binding on parietal cell H2 receptors which stimulate acid secretion, and other substances that promote acid secretion (such as gastrin and acetylcholine) have a reduced effect on parietal cells when the H2 receptors are blocked.
Structure
Thumb
Synonyms
ValueSource
RoxatidineChEMBL
Roxatidine acetic acidGenerator
AceroxatidineHMDB
PifatidineHMDB
RoxatidinaHMDB
RoxatidinumHMDB
Chemical FormulaC19H28N2O4
Average Molecular Weight348.4366
Monoisotopic Molecular Weight348.204907394
IUPAC Name({3-[3-(piperidin-1-ylmethyl)phenoxy]propyl}carbamoyl)methyl acetate
Traditional Nameroxatidine acetate
CAS Registry Number78628-28-1
SMILES
CC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C1
InChI Identifier
InChI=1S/C19H28N2O4/c1-16(22)25-15-19(23)20-9-6-12-24-18-8-5-7-17(13-18)14-21-10-3-2-4-11-21/h5,7-8,13H,2-4,6,9-12,14-15H2,1H3,(H,20,23)
InChI KeyInChIKey=SMTZFNFIKUPEJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassBenzylpiperidines
Direct ParentN-benzylpiperidines
Alternative Parents
Substituents
  • N-benzylpiperidine
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Acetate salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 146 (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.061 mg/mLALOGPS
logP2.27ALOGPS
logP1.31ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.88ChemAxon
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.87 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.32 m3·mol-1ChemAxon
Polarizability39.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Roxatidine acetate Action PathwaySMP00734Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08806
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08806
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08806
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRoxatidine
NuGOwiki LinkHMDB15695
Metagene LinkHMDB15695
METLIN IDNot Available
PubChem Compound5105
PDB IDNot Available
ChEBI ID171339
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Product Insert [Link]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
References
  1. Agrawal SS, Alvin Jose M: Roxatidine, an H(2) receptor blocker, is an estrogenic compound--experimental evidence. Syst Biol Reprod Med. 2010 Aug;56(4):286-91. [20718616 ]