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Roxatidine acetate

July 24, 2017
Common Name

Roxatidine acetate Description

Roxatidine 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-stimliated 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 stimliate 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ROXATIDINEChEMBL Roxatidine acetic acidGenerator AceroxatidineHMDB PifatidineHMDB RoxatidinaHMDB RoxatidinumHMDB Roxatidine acetate hydrochlorideMeSH ZarocsMeSH RoxiwasMeSH

Chemical Formlia

C19H28N2O4 Average Molecliar Weight

348.4366 Monoisotopic Molecliar Weight

348.204907394 IUPAC Name

({3-[3-(piperidin-1-ylmethyl)phenoxy]propyl}carbamoyl)methyl acetate Traditional Name

roxatidine acetate CAS Registry Number

78628-28-1 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 Key

SMTZFNFIKUPEJC-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Piperidines Direct Parent

N-benzylpiperidines Alternative Parents

  • Benzylamines
  • Phenol ethers
  • Phenoxy compounds
  • Phenylmethylamines
  • Alkyl aryl ethers
  • Aralkylamines
  • Amino acids and derivatives
  • Carboxylic acid esters
  • Secondary carboxylic acid amides
  • Trialkylamines
  • Monocarboxylic acids and derivatives
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Ulcer Agents
  • Histamine H2 Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point145 – 146 (hydrochloride salt)Not Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Roxatidine acetate Action PathwaySMP00734Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08806

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08806

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08806 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4926 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Roxatidine NuGOwiki Link

    HMDB15695 Metagene Link

    HMDB15695 METLIN ID

    Not Available PubChem Compound

    5105 PDB ID

    Not Available ChEBI ID

    171339

    Product: Guanabenz (Acetate)

    References Synthesis Reference Not 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 ]

    PMID: 12446593

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