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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:37:10 UTC
Update Date2019-07-23 14:38:52 UTC
HMDB IDHMDB0240224
Secondary Accession NumbersNone
Metabolite Identification
Common NameChlorcyclizine
DescriptionChlorcyclizine, also known as di-paralene or 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. Chlorcyclizine is a very strong basic compound (based on its pKa). In humans, chlorcyclizine is involved in chlorcyclizine h1-antihistamine action. High concentrations of the N-desmethyl metabolite are found in the liver, lungs, kidney, and spleen. Chlorcyclizine is a first generation phenylpiperazine class antihistamine used to treat urticaria, rhinitis, pruritus, and other allergy symptoms. Chlorcyclizine also has some local anesthetic, anticholinergic, and antiserotonergic properties, and can be used as an antiemetic.
Structure
Data?1563892732
Synonyms
ValueSource
TrihistanHMDB
Di-paraleneHMDB
MantadilHMDB
PruresidineHMDB
HistachlorazineHMDB
ChlorcyclineHMDB
ChlorocyclizinHMDB
AlergicideHMDB
ChlorocyclineHMDB
(±)-chlorcyclizineHMDB
Compound 47-282HMDB
Di-paralenHMDB
N-Methyl-n'-(4-chlorobenzhydryl)piperazineHMDB
NSC 25246HMDB
PerazylHMDB
ChlorcyclizineHMDB
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 Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-9261000000-d789fa33e2113c522133Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-9261000000-d789fa33e2113c522133Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-8790000000-55311c996650b7e8c280Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-b26de1d44bba1bbba71dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-cd86d2a7b60fba9a8093Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0490000000-d2ef728df7bda2d67974Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0920000000-6337d2bca22bf828e822Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-cb2916a03edaa19b1b71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-26236f7b47a790c10e10Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3c7d8992d76da5c7bd63Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-a5c6cf14866d0a23a877Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02t9-2900000000-5462dc3ded9a8297443eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-c4ac9541a144f323398eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxr-0590000000-ce9f2e2451aeb092dd88Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0920000000-587c135265c1fbd939dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-2788ec685444238cbb77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-300ed2322e3d24ba24cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0009000000-6b6c6de087e1c9ad671eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udl-1192000000-2e1124f2124d4e765271Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udl-1290000000-cf510eabf20fd368c6d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gdi-2890000000-77c12238ddf4cb2c7502Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-1930000000-89c336a1c9b2a2f0a9b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-cd18f1e6a9392e477758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1195000000-56f33fe9d96ff1da46d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6980000000-931f090bcc929d51f9f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-897899954ed2f06ae95bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1090000000-4be8b22bd980ebc5f053Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mx-7590000000-e863060ef85ea8728681Spectrum
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 IDNot Available
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
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 ]