Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:05 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
Data?1582753324
Synonyms
ValueSource
Roxatidine acetic acidGenerator
ROXATIDINEHMDB
AceroxatidineHMDB
PifatidineHMDB
RoxatidinaHMDB
RoxatidinumHMDB
Roxatidine acetate hydrochlorideHMDB
ZarocsHMDB
RoxiwasHMDB
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
Description 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 - 146 (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.531661259
DarkChem[M-H]-179.97831661259
DeepCCS[M+H]+185.23530932474
DeepCCS[M-H]-182.87730932474
DeepCCS[M-2H]-215.76330932474
DeepCCS[M+Na]+191.32830932474
AllCCS[M+H]+181.632859911
AllCCS[M+H-H2O]+179.032859911
AllCCS[M+NH4]+183.932859911
AllCCS[M+Na]+184.632859911
AllCCS[M-H]-182.432859911
AllCCS[M+Na-2H]-183.132859911
AllCCS[M+HCOO]-184.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Roxatidine acetateCC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C12994.9Standard polar33892256
Roxatidine acetateCC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C12743.5Standard non polar33892256
Roxatidine acetateCC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C12796.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Roxatidine acetate,1TMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C2798.5Semi standard non polar33892256
Roxatidine acetate,1TMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C2632.4Standard non polar33892256
Roxatidine acetate,1TMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C3628.5Standard polar33892256
Roxatidine acetate,1TBDMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C(C)(C)C2992.3Semi standard non polar33892256
Roxatidine acetate,1TBDMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C(C)(C)C2797.6Standard non polar33892256
Roxatidine acetate,1TBDMS,isomer #1CC(=O)OCC(=O)N(CCCOC1=CC=CC(CN2CCCCC2)=C1)[Si](C)(C)C(C)(C)C3708.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Roxatidine acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9760000000-71f6584b19a0f5b1ab872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Roxatidine acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Roxatidine acetate 35V, Positive-QTOFsplash10-006t-0945000000-793ce59b362fbcb997042021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 10V, Positive-QTOFsplash10-0002-1393000000-5d3a5b061a40e81444ef2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 20V, Positive-QTOFsplash10-01pk-2981000000-98094c93da0344b9e8632016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 40V, Positive-QTOFsplash10-08mi-5910000000-e230f67660b30078b21a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 10V, Negative-QTOFsplash10-052e-9535000000-c5e7ccdb9ff9018af0932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 20V, Negative-QTOFsplash10-0006-7922000000-ee09764a33843ac386b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 40V, Negative-QTOFsplash10-0006-9600000000-7aa008037322a24c00542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 10V, Positive-QTOFsplash10-0002-0098000000-761f3342cee5cf0bff8e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 20V, Positive-QTOFsplash10-000t-2291000000-f58f1ae6b429f7bc9ec12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 40V, Positive-QTOFsplash10-0002-9600000000-1ac26d856ca188b5f8a42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 10V, Negative-QTOFsplash10-002g-7597000000-39442e924ae1cb6d3a5b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 20V, Negative-QTOFsplash10-0a4i-9312000000-6aab40c58e448964af982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roxatidine acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-5c40d562e4dddf6501e72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08806 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]