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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-10-17 09:58:23 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005032
Secondary Accession Numbers
  • HMDB05032
Metabolite Identification
Common NameCetirizine
DescriptionCetirizine is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth. A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects. Cetirizine hydrochloride is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth.
Structure
Data?1582752341
Synonyms
ValueSource
CetirizinChEBI
CetirizinaChEBI
CetirizinumChEBI
CetidermKegg
BenadayHMDB
Cetirizine hydrochlorideHMDB
HumexHMDB
ReactineHMDB, MeSH
VirlixHMDB, MeSH
ZirtekHMDB, MeSH
ZyrlexHMDB
ZyrtecHMDB, MeSH
Alpharma brand OF cetirizine dihydrochlorideMeSH, HMDB
Ceti-purenMeSH, HMDB
CetiLichMeSH, HMDB
CetirigammaMeSH, HMDB
Cetirizin alMeSH, HMDB
Dihydrochloride, cetirizineMeSH, HMDB
glaxo Wellcome brand OF cetirizine dihydrochlorideMeSH, HMDB
TAD brand OF cetirizine dihydrochlorideMeSH, HMDB
UCB brand OF cetirizine dihydrochlorideMeSH, HMDB
VoltricMeSH, HMDB
CT-Arzneimittel brand OF cetirizine dihydrochlorideMeSH, HMDB
Azupharma brand OF cetirizine dihydrochlorideMeSH, HMDB
Basics brand OF cetirizine dihydrochlorideMeSH, HMDB
CetalergMeSH, HMDB
Dermapharm brand OF cetirizine dihydrochlorideMeSH, HMDB
Krewel brand OF cetirizine dihydrochlorideMeSH, HMDB
Lacer brand OF cetirizine dihydrochlorideMeSH, HMDB
Menarini brand OF cetirizine dihydrochlorideMeSH, HMDB
Pfizer brand OF cetirizine dihydrochlorideMeSH, HMDB
Pfizer consumer healthcare brand OF cetirizine dihydrochlorideMeSH, HMDB
UCB pharma brand OF cetirizine dihydrochlorideMeSH, HMDB
AWD.pharma brand OF cetirizine dihydrochlorideMeSH, HMDB
Aliud brand OF cetirizine dihydrochlorideMeSH, HMDB
Ceti tadMeSH, HMDB
CetiduraMeSH, HMDB
Cetirizin azuMeSH, HMDB
Cetirizine dihydrochlorideMeSH, HMDB
CetirlanMeSH, HMDB
Lichtenstein brand OF cetirizine dihydrochlorideMeSH, HMDB
Rodleben brand OF cetirizineMeSH, HMDB
United drug brand OF cetirizine dihydrochlorideMeSH, HMDB
Wolff brand OF cetirizine dihydrochlorideMeSH, HMDB
(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic acidMeSH, HMDB
AlerlisinMeSH, HMDB
CeterifugMeSH, HMDB
Cetil von CTMeSH, HMDB
Cetirizin basicsMeSH, HMDB
Merck dura brand OF cetirizine dihydrochlorideMeSH, HMDB
Sanofi synthelabo brand OF cetirizine dihydrochlorideMeSH, HMDB
Wörwag brand OF cetirizine dihydrochlorideMeSH, HMDB
ZetirMeSH, HMDB
Chemical FormulaC21H25ClN2O3
Average Molecular Weight388.888
Monoisotopic Molecular Weight388.155370383
IUPAC Name2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Traditional Namecetirizine
CAS Registry Number83881-51-0
SMILES
OC(=O)COCCN1CCN(CC1)C(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)
InChI KeyZKLPARSLTMPFCP-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
  • 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 Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point112.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM200.830932474
[M+H]+Not Available198.285http://allccs.zhulab.cn/database/detail?ID=AllCCS00000754
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP2.98ALOGPS
logP0.86ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)7.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.01 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.87 m³·mol⁻¹ChemAxon
Polarizability41.88 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
DeepCCS[M+H]+187.42630932474
DeepCCS[M-H]-184.95730932474
DeepCCS[M-2H]-219.16630932474
DeepCCS[M+Na]+194.60630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CetirizineOC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C14076.7Standard polar33892256
CetirizineOC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C13009.0Standard non polar33892256
CetirizineOC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C13029.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cetirizine,1TMS,isomer #1C[Si](C)(C)OC(=O)COCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13104.7Semi standard non polar33892256
Cetirizine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13312.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-3292000000-e20abaab20740ce81a182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetirizine GC-MS (1 TMS) - 70eV, Positivesplash10-0uds-7498000000-d6daecf118171395d6b72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cetirizine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000j-0900000000-9801bb859e79fa9922aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-014b559d56b0f32984ff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-213bd47e17d5ab69ad4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-004r-9006000000-f496e22c8e0e293fe98c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-d8a55ab1a7aff0580a912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-d8a55ab1a7aff0580a912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-dc957bb6f947575ae4fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000b-0900000000-48fc0581ff9fff15e16d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-04ca95fadd952d0aaeb82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-000i-0009000000-014b559d56b0f32984ff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-0006-0009000000-26a7769df28c2325ec532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOFsplash10-0006-0009000000-284c2e7b25733d7c98752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-QFT , negative-QTOFsplash10-000i-0009000000-04befed283d691217ba22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-14715ff4d57580fbb1662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-0f79-0069000000-431df9c3533b77cf08bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-e042b67e2048318e7dbd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-b0dfb67717c01fd0c0b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0970000000-e2810b242fefb4a419e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-72f7cddc4ff6d45f98c02017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 10V, Positive-QTOFsplash10-000i-0019000000-e2cc239f762011eb0c4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 20V, Positive-QTOFsplash10-0w2i-1169000000-185e6899ae017256a7672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 40V, Positive-QTOFsplash10-0udi-3391000000-bfd70499959ae71093eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 10V, Negative-QTOFsplash10-000i-0009000000-caf1604c9603d45a67122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 20V, Negative-QTOFsplash10-000i-1119000000-61c40cd9a0e9b76b5e912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cetirizine 40V, Negative-QTOFsplash10-056r-9162000000-08731719ee47b215e4c72016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2577
KEGG Compound IDC07778
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCetirizine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID3561
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCossement, Eric; Motte, Genevieve; Bodson, Guy; Gobert, Jean. A., Process for preparation of cetirizine, its dihydrochloride, and optical isomers via hydrolysis and corresponding nitriles. Brit. UK Pat. Appl. (1990), 13 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093 ]
  2. Purohit A, Melac M, Pauli G, Frossard N: Comparative activity of cetirizine and desloratadine on histamine-induced wheal-and-flare responses during 24 hours. Ann Allergy Asthma Immunol. 2004 Jun;92(6):635-40. [PubMed:15237765 ]
  3. Ramboer I, Bumtbacea R, Lazarescu D, Radu JR: Cetirizine and loratadine: a comparison using the ED50 in skin reactions. J Int Med Res. 2000 Mar-Apr;28(2):69-77. [PubMed:10898119 ]
  4. Purohit A, Duvernelle C, Melac M, Pauli G, Frossard N: Twenty-four hours of activity of cetirizine and fexofenadine in the skin. Ann Allergy Asthma Immunol. 2001 Apr;86(4):387-92. [PubMed:11345280 ]
  5. Townley RG, Okada C: Use of cetirizine to investigate non-H1 effects of second-generation antihistamines. Ann Allergy. 1992 Feb;68(2):190-6. [PubMed:1346737 ]
  6. Brik A, Tashkin DP, Gong H Jr, Dauphinee B, Lee E: Effect of cetirizine, a new histamine H1 antagonist, on airway dynamics and responsiveness to inhaled histamine in mild asthma. J Allergy Clin Immunol. 1987 Jul;80(1):51-6. [PubMed:2885355 ]
  7. Fadel R, Herpin-Richard N, Rihoux JP, Henocq E: Inhibitory effect of cetirizine 2HCl on eosinophil migration in vivo. Clin Allergy. 1987 Jul;17(4):373-9. [PubMed:2887304 ]
  8. Petersen LJ, Church MK, Rihoux JP, Skov PS: Measurement of interstitial cetirizine concentrations in human skin: correlation of drug levels with inhibition of histamine-induced skin responses. Allergy. 1999 Jun;54(6):607-11. [PubMed:10435475 ]
  9. Siergiejko Z, Michalska I, Rogalewska A, Chyrek-Borowska S: [Effect of cetirizine, selective H1 antagonist of histamine on skin and bronchial reactivity and cellular histamine release in allergic diseases]. Pneumonol Alergol Pol. 1992;60(11-12):22-7. [PubMed:1303774 ]
  10. Atkins PC, Zweiman B, Moskovitz A, von Allmen C, Ciliberti M: Cellular inflammatory responses and mediator release during early developing late-phase allergic cutaneous inflammatory responses: effects of cetirizine. J Allergy Clin Immunol. 1997 Jun;99(6 Pt 1):806-11. [PubMed:9215249 ]
  11. Simons FE, Murray HE, Simons KJ: Quantitation of H1-receptor antagonists in skin and serum. J Allergy Clin Immunol. 1995 Mar;95(3):759-64. [PubMed:7897161 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6