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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014697
Secondary Accession Numbers
  • HMDB14697
Metabolite Identification
Common NameHydroxyzine
DescriptionHydroxyzine, also known as hidroxizina or hychotine, 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. A N-alkylpiperazine that is piperzine in which the nitrogens atoms are substituted by 2-(2-hydroxyethoxy)ethyl and (4-chlorophenyl)(phenyl)methyl groups respectively. Hydroxyzine is a very strong basic compound (based on its pKa). In humans, hydroxyzine is involved in hydroxyzine h1-antihistamine action. Hydroxyzine is a potentially toxic compound.
Structure
Data?1582753210
Synonyms
ValueSource
HidroxizinaChEBI
HychotineChEBI
HydroxineChEBI
HydroxizineChEBI
HydroxizinumChEBI
HydroxycineChEBI
HydroxyzinChEBI
HydroxyzinumChEBI
MarexKegg
Hydroxyzine baseHMDB
Hydroxyzine pamoateHMDB
HydroxyzyneHMDB
IdrossizinaHMDB
AtaraxHMDB
Hydroxyzine hydrochlorideHMDB
OrgatraxHMDB
2-(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)ethanolHMDB
Hydroxyzine dihydrochlorideHMDB
VistarilHMDB
DurraxHMDB
Pamoate, hydroxyzineHMDB
Chemical FormulaC21H27ClN2O2
Average Molecular Weight374.904
Monoisotopic Molecular Weight374.176105825
IUPAC Name2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol
Traditional Namehydroxyzine
CAS Registry Number68-88-2
SMILES
OCCOCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C21H27ClN2O2/c22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-9,21,25H,10-17H2
InChI KeyZQDWXGKKHFNSQK-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
  • Aralkylamine
  • Halobenzene
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Dialkyl ether
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.091 g/LNot Available
LogP2.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM197.430932474
[M+H]+Not Available195.398http://allccs.zhulab.cn/database/detail?ID=AllCCS00000803
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.091 g/LALOGPS
logP3.43ALOGPS
logP3.41ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)7.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.07 m³·mol⁻¹ChemAxon
Polarizability41.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.91430932474
DeepCCS[M-H]-185.55630932474
DeepCCS[M-2H]-219.34630932474
DeepCCS[M+Na]+194.82130932474
AllCCS[M+H]+189.532859911
AllCCS[M+H-H2O]+186.832859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.832859911
AllCCS[M-H]-191.732859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-192.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydroxyzineOCCOCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C13569.3Standard polar33892256
HydroxyzineOCCOCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12857.8Standard non polar33892256
HydroxyzineOCCOCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12865.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxyzine,1TMS,isomer #1C[Si](C)(C)OCCOCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13008.9Semi standard non polar33892256
Hydroxyzine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCOCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC13190.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hydroxyzine EI-B (Non-derivatized)splash10-0udi-6491000000-95c46c16c2b29900f4d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxyzine EI-B (Non-derivatized)splash10-0udi-6491000000-95c46c16c2b29900f4d92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyzine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-4291000000-5750700bc5e75e5811022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyzine GC-MS (1 TMS) - 70eV, Positivesplash10-0udr-6589100000-8c29584ceed7772070422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyzine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyzine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uxr-4591000000-d2e3424c44feae8a5d9c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine , positive-QTOFsplash10-0udi-0593000000-f20d2328497a3a80239b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 30V, Positive-QTOFsplash10-0udi-0090000000-1775dbd78559702d467d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 15V, Positive-QTOFsplash10-0ufr-0095000000-2486fd8f41ddb000ef302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 45V, Positive-QTOFsplash10-0udi-0490000000-34f4ae7f6d96a96d81742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 60V, Positive-QTOFsplash10-014i-0920000000-4a9f93b8b1f05c5bbf5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 45V, Positive-QTOFsplash10-0udi-0490000000-a0279bcdd59b767b1c232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 75V, Positive-QTOFsplash10-014i-0900000000-11dd6f0d87e2b77549b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyzine 90V, Positive-QTOFsplash10-014i-0900000000-3f8b71c3d5770c87aee12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 10V, Positive-QTOFsplash10-004i-0019000000-f6d89e75a6d7e8af90012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 20V, Positive-QTOFsplash10-0w4i-3179000000-af704769cca5c3dc8e6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 40V, Positive-QTOFsplash10-0udj-5292000000-d581a3d2a57e2fa067fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 10V, Negative-QTOFsplash10-00di-1009000000-753db826ff35e907de512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 20V, Negative-QTOFsplash10-00di-2029000000-b8ad29be99c096f6967a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 40V, Negative-QTOFsplash10-01ox-9061000000-5b2e7de6b58b52c401772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 10V, Negative-QTOFsplash10-00di-1009000000-ce968b789a986f8f3fc32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 20V, Negative-QTOFsplash10-0abc-9016000000-407400d539246a74d9422021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 40V, Negative-QTOFsplash10-0w5c-3291000000-5bcbb07a54b5bbc8895e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 10V, Positive-QTOFsplash10-0fb9-0079000000-7d6c850012f146c2d0742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 20V, Positive-QTOFsplash10-0udi-0090000000-35c9b971bf421f75d3912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyzine 40V, Positive-QTOFsplash10-0udi-2191000000-2083d212703dd6c907432021-09-24Wishart 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 DB00557 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00557 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 IDDB00557
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3531
KEGG Compound IDC07045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxyzine
METLIN IDNot Available
PubChem Compound3658
PDB IDNot Available
ChEBI ID5818
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. Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. [PubMed:7103423 ]
  2. HUTCHEON DE, MORRIS DL, SCRIABINE A: Cardiovascular action of hydroxyzine (atarax). J Pharmacol Exp Ther. 1956 Dec;118(4):451-60. [PubMed:13385806 ]
  3. DOLAN CM: Management of emotional disturbances; use of hydroxyzine (atarax) in general practice. Calif Med. 1958 Jun;88(6):443-4. [PubMed:13536863 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Spahr L, Coeytaux A, Giostra E, Hadengue A, Annoni JM: Histamine H1 blocker hydroxyzine improves sleep in patients with cirrhosis and minimal hepatic encephalopathy: a randomized controlled pilot trial. Am J Gastroenterol. 2007 Apr;102(4):744-53. Epub 2007 Jan 11. [PubMed:17222324 ]
  3. Sakaguchi T, Itoh H, Ding WG, Tsuji K, Nagaoka I, Oka Y, Ashihara T, Ito M, Yumoto Y, Zenda N, Higashi Y, Takeyama Y, Matsuura H, Horie M: Hydroxyzine, a first generation H(1)-receptor antagonist, inhibits human ether-a-go-go-related gene (HERG) current and causes syncope in a patient with the HERG mutation. J Pharmacol Sci. 2008 Dec;108(4):462-71. Epub 2008 Dec 5. [PubMed:19057127 ]
  4. Chen C: Physicochemical, pharmacological and pharmacokinetic properties of the zwitterionic antihistamines cetirizine and levocetirizine. Curr Med Chem. 2008;15(21):2173-91. [PubMed:18781943 ]
  5. Snowman AM, Snyder SH: Cetirizine: actions on neurotransmitter receptors. J Allergy Clin Immunol. 1990 Dec;86(6 Pt 2):1025-8. [PubMed:1979798 ]