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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:37:27 UTC
Update Date2019-07-23 14:38:52 UTC
HMDB IDHMDB0240225
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxatomide
DescriptionOxatomide, also known as celtect or tinset, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Oxatomide, sold under the brand name Tinset among others, is a first-generation antihistamine of the diphenylmethylpiperazine family which is marketed in Europe, Japan, and a number of other countries. Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group. Oxatomide is a drug. Oxatomide is a very strong basic compound (based on its pKa). In humans, oxatomide is involved in oxatomide h1-antihistamine action. It was patented in 1976 and came into medical use in 1981. In addition to its H1 receptor antagonism, it also possesses antiserotonergic activity similarly to hydroxyzine. Reaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). It was discovered at Janssen Pharmaceutica in 1975. Oxatomide lacks any anticholinergic effects. Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3).
Structure
Data?1563892732
Synonyms
ValueSource
CeltectKegg
TinsetHMDB
OxatimideHMDB
CobionaHMDB
DastenHMDB
KW 4354HMDB
NSC 309710HMDB
R 35443HMDB
OxatomideHMDB, MeSH
Chemical FormulaC27H30N4O
Average Molecular Weight426.564
Monoisotopic Molecular Weight426.241961602
IUPAC Name1-{3-[4-(diphenylmethyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-1,3-benzodiazol-2-one
Traditional Nameoxatomide
CAS Registry Number60607-34-3
SMILES
O=C1NC2=C(C=CC=C2)N1CCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C27H30N4O/c32-27-28-24-14-7-8-15-25(24)31(27)17-9-16-29-18-20-30(21-19-29)26(22-10-3-1-4-11-22)23-12-5-2-6-13-23/h1-8,10-15,26H,9,16-21H2,(H,28,32)
InChI KeyBAINIUMDFURPJM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzimidazole
  • N-alkylpiperazine
  • Aralkylamine
  • 1,4-diazinane
  • N-substituted imidazole
  • Piperazine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.71ALOGPS
logP4.62ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)12.92ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.94 m³·mol⁻¹ChemAxon
Polarizability48.56 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0220900000-cc17eb9e27e757293746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0170-0940300000-4a2a5de4a32bcd86e86aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3930000000-458ccd12f5ae59be98d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0100900000-f3d9f74bd5c101766086Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-0921700000-eb30950f94d7d9158786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1900000000-b20088329067e560532cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12877
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4454
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxatomide
METLIN IDNot Available
PubChem Compound4615
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohmori K, Ishii H, Nito M, Shuto K, Nakamizo N: [Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators]. Nihon Yakurigaku Zasshi. 1983 May;81(5):399-409. [PubMed:6138301 ]