Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:37:10 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240224
Secondary Accession NumbersNone
Metabolite Identification
Common NameChlorcyclizine
DescriptionChlorcyclizine, also known as histachlorazine, 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, chlorcyclizine is involved in the chlorcyclizine h1-antihistamine action pathway. Chlorcyclizine 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 a significant number of articles have been published on Chlorcyclizine.
Structure
Data?1563892732
Synonyms
ValueSource
HistachlorazineMeSH
ChlorcyclineMeSH
ChlorocyclizinMeSH
AlergicideHMDB
ChlorocyclineHMDB
(±)-ChlorcyclizineHMDB
Compound 47-282HMDB
Di-ParalenHMDB
N-Methyl-N'-(4-chlorobenzhydryl)piperazineHMDB
NSC 25246HMDB
PerazylHMDB
TrihistanHMDB, ChEMBL
ChlorcyclizineHMDB
Di-paraleneChEMBL, HMDB
MantadilChEMBL, HMDB
PruresidineChEMBL, HMDB
Chemical FormulaC18H21ClN2
Average Molecular Weight300.826
Monoisotopic Molecular Weight300.139326389
IUPAC Name1-[(4-chlorophenyl)(phenyl)methyl]-4-methylpiperazine
Traditional Namechlorcyclizine
CAS Registry Number82-93-9
SMILES
CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
InChI KeyWFNAKBGANONZEQ-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-methylpiperazine
  • Aralkylamine
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • 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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available173.374http://allccs.zhulab.cn/database/detail?ID=AllCCS00000781
Predicted Molecular Properties
PropertyValueSource
logP4.16ALOGPS
logP4.15ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)7.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.74 m³·mol⁻¹ChemAxon
Polarizability33.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+170.50330932474
DeepCCS[M-H]-168.14630932474
DeepCCS[M-2H]-201.03130932474
DeepCCS[M+Na]+176.59730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorcyclizineCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12976.1Standard polar33892256
ChlorcyclizineCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12260.7Standard non polar33892256
ChlorcyclizineCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12258.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Chlorcyclizine EI-B (Non-derivatized)splash10-006t-9261000000-d789fa33e2113c5221332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlorcyclizine EI-B (Non-derivatized)splash10-006t-9261000000-d789fa33e2113c5221332018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorcyclizine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-8790000000-55311c996650b7e8c2802017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorcyclizine 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 - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-b26de1d44bba1bbba71d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-cd86d2a7b60fba9a80932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udi-0490000000-d2ef728df7bda2d679742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0920000000-6337d2bca22bf828e8222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-cb2916a03edaa19b1b712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-26236f7b47a790c10e102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-3c7d8992d76da5c7bd632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-a5c6cf14866d0a23a8772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-02t9-2900000000-5462dc3ded9a8297443e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udi-0090000000-c4ac9541a144f323398e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0uxr-0590000000-ce9f2e2451aeb092dd882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0920000000-587c135265c1fbd939db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-2788ec685444238cbb772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-300ed2322e3d24ba24cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-0009000000-6b6c6de087e1c9ad671e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udl-1192000000-2e1124f2124d4e7652712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0udl-1290000000-cf510eabf20fd368c6d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-0gdi-2890000000-77c12238ddf4cb2c75022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorcyclizine LC-ESI-QFT , positive-QTOFsplash10-014i-1930000000-89c336a1c9b2a2f0a9b72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 10V, Positive-QTOFsplash10-0udi-0019000000-cd18f1e6a9392e4777582017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 20V, Positive-QTOFsplash10-0udi-1195000000-56f33fe9d96ff1da46d02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 40V, Positive-QTOFsplash10-0udi-6980000000-931f090bcc929d51f9f72017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 10V, Negative-QTOFsplash10-0002-0090000000-897899954ed2f06ae95b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 20V, Negative-QTOFsplash10-0002-1090000000-4be8b22bd980ebc5f0532017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorcyclizine 40V, Negative-QTOFsplash10-00mx-7590000000-e863060ef85ea87286812017-07-26Wishart 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 IDDB08936
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2609
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorcyclizine
METLIN IDNot Available
PubChem Compound2710
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. He S, Lin B, Chu V, Hu Z, Hu X, Xiao J, Wang AQ, Schweitzer CJ, Li Q, Imamura M, Hiraga N, Southall N, Ferrer M, Zheng W, Chayama K, Marugan JJ, Liang TJ: Repurposing of the antihistamine chlorcyclizine and related compounds for treatment of hepatitis C virus infection. Sci Transl Med. 2015 Apr 8;7(282):282ra49. doi: 10.1126/scitranslmed.3010286. [PubMed:25855495 ]