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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:37:51 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240226
Secondary Accession NumbersNone
Metabolite Identification
Common NameLevocetirizine
DescriptionLevocetirizine, also known as xazal, 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. In humans, levocetirizine is involved in the levocetirizine h1-antihistamine action pathway. Levocetirizine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Levocetirizine.
Structure
Data?1563892732
Synonyms
ValueSource
XazalKegg
(-)-CetirizineHMDB
(R)-CetirizineHMDB
LevocetirizineHMDB
Levocetirizine dihydrochlorideMeSH, HMDB
(2-(4-((R)-P-chloro-alpha-Phenylbenzyl)-1-piperazinyl)ethoxy)acetic acidMeSH, HMDB
XyzalMeSH, HMDB
XusalMeSH, HMDB
LevocetrizineMeSH, HMDB
Acetic acid, (2-(4-((R)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, dihydrochlorideMeSH
(2-(4-((R)-(4-Chlorophenyl)phenylmethyl)piperazin-1-yl)ethoxy)acetic acid dihydrochlorideMeSH
Cetirizine (R)-form dihydrochlorideMeSH
Levocetirizine hydrochlorideMeSH
Chemical FormulaC21H25ClN2O3
Average Molecular Weight388.89
Monoisotopic Molecular Weight388.1553704
IUPAC Name2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Traditional Name(-)-cetirizine
CAS Registry Number130018-77-8
SMILES
OC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)/t21-/m1/s1
InChI KeyZKLPARSLTMPFCP-OAQYLSRUSA-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
  • Chlorobenzene
  • Halobenzene
  • N-alkylpiperazine
  • Aralkylamine
  • Aryl halide
  • 1,4-diazinane
  • Aryl chloride
  • Piperazine
  • Amino acid
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Amine
  • Organochloride
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.98ALOGPS
logP0.87ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)7.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.01 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.87 m³·mol⁻¹ChemAxon
Polarizability41.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+191.17331661259
AllCCS[M-H]-192.99631661259
DeepCCS[M+H]+188.54930932474
DeepCCS[M-H]-186.19130932474
DeepCCS[M-2H]-220.35630932474
DeepCCS[M+Na]+195.66530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LevocetirizineOC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C14118.7Standard polar33892256
LevocetirizineOC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C12958.2Standard non polar33892256
LevocetirizineOC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C13031.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levocetirizine,1TMS,isomer #1C[Si](C)(C)OC(=O)COCCN1CCN([C@H](C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13104.8Semi standard non polar33892256
Levocetirizine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COCCN1CCN([C@H](C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13296.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levocetirizine 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 - Levocetirizine LC-ESI-QTOF , positive-QTOFsplash10-000i-0019000000-e24b60aef9a19aa0ca892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-4fbbabe7bf3d0ad4cab52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0190000000-8783499dc5c2d31a3f7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine LC-ESI-QTOF , positive-QTOFsplash10-0uxr-0790000000-4efaf73700a535eb98e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine LC-ESI-QTOF , positive-QTOFsplash10-014i-0920000000-f952b59e46cde6d2cfac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine , positive-QTOFsplash10-0udi-0492000000-90537be4971a327c0fb12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 10V, Positive-QTOFsplash10-000i-0019000000-58e20ce62a59f675cad02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 35V, Negative-QTOFsplash10-000i-0009000000-58c22d9c2a348a178a482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 50V, Positive-QTOFsplash10-014i-0920000000-0748e88c1e23b2b0200e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 35V, Positive-QTOFsplash10-0udi-0390000000-efda2d1abd40f8bd94fe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 20V, Positive-QTOFsplash10-0udi-0090000000-a60f7bcdabd639aa21dd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 10V, Positive-QTOFsplash10-000i-0019000000-76518322dde4393172732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 30V, Positive-QTOFsplash10-0udi-0190000000-c4bdb447141670af52f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levocetirizine 40V, Positive-QTOFsplash10-0uxr-0790000000-872a3be1b72397cf7c9f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 10V, Positive-QTOFsplash10-000i-0019000000-e2cc239f762011eb0c4d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 20V, Positive-QTOFsplash10-0w2i-1169000000-185e6899ae017256a7672017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 40V, Positive-QTOFsplash10-0udi-3391000000-bfd70499959ae71093eb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 10V, Negative-QTOFsplash10-000i-0009000000-caf1604c9603d45a67122017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 20V, Negative-QTOFsplash10-000i-1119000000-61c40cd9a0e9b76b5e912017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 40V, Negative-QTOFsplash10-056r-9162000000-08731719ee47b215e4c72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 10V, Negative-QTOFsplash10-00kr-0019000000-0c5e69814c3e65c1bb032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 20V, Negative-QTOFsplash10-00kr-3069000000-040dc5b68ae9b49650d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 40V, Negative-QTOFsplash10-0h0u-3292000000-27313a2e9a6a6cb48e7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 10V, Positive-QTOFsplash10-0f79-0089000000-3f59e7cc38d9510dbdaf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levocetirizine 20V, Positive-QTOFsplash10-0udi-0090000000-35c9b971bf421f75d3912021-09-24Wishart LabView Spectrum
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 IDDB06282
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1266001
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevocetirizine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Snidvongs K, Seresirikachorn K, Khattiyawittayakun L, Chitsuthipakorn W: Sedative Effects of Levocetirizine: A Systematic Review and Meta-Analysis of Randomized Controlled Studies. Drugs. 2017 Feb;77(2):175-186. doi: 10.1007/s40265-016-0682-0. [PubMed:28070872 ]