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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-20 20:33:08 UTC
HMDB IDHMDB0015695
Secondary Accession Numbers
  • HMDB15695
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
Roxatidine acetate hydrochlorideMeSH
ZarocsMeSH
RoxiwasMeSH
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 KeySMTZFNFIKUPEJC-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
  • Phenoxy compound
  • Benzylamine
  • Phenol ether
  • Phenylmethylamine
  • Alkyl aryl ether
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.32 m³·mol⁻¹ChemAxon
Polarizability39.26 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9760000000-71f6584b19a0f5b1ab87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1393000000-5d3a5b061a40e81444efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-2981000000-98094c93da0344b9e863View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-5910000000-e230f67660b30078b21aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052e-9535000000-c5e7ccdb9ff9018af093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-7922000000-ee09764a33843ac386b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-7aa008037322a24c0054View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Roxatidine acetate Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08806 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08806 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08806
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRoxatidine acetate
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. doi: 10.3109/19396368.2010.496894. [PubMed:20718616 ]