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Cyclizine

July 24, 2017
Common Name

Cyclizine Description

Cyclizine is only found in individuals that have used or taken this drug. It is a histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmfli substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medlila region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibliar apparatus to the vomiting centre. Motion sickness principally involves overstimliation of these pathways due to various sensory stimlii. Hence the action of cyclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since cyclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+-)-1-Diphenylmethyl-4-methylpiperazineChEBI (N-Benzhydryl)(n'-methyl)diethylenediamineChEBI 1-(Diphenylmethyl)-4-methylpiperazineChEBI 1-Benzhydryl-4-methylpiperazinChEBI CiclizinaChEBI CyclizinumChEBI N-Benzhydryl-n'-methylpiperazineChEBI N-Methyl-n'-benzhydrylpiperazineChEBI Cyclizine chlorideHMDB Cyclizine hydrochlorideMeSH HCL, CyclizineMeSH MarezineMeSH Cyclizine HCLMeSH Hydrochloride, cyclizineMeSH

Chemical Formlia

C18H22N2 Average Molecliar Weight

266.3807 Monoisotopic Molecliar Weight

266.178298714 IUPAC Name

1-(diphenylmethyl)-4-methylpiperazine Traditional Name

cyclizine CAS Registry Number

82-92-8 SMILES

CN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

InChI Key

UVKZSORBKUEBAZ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Diphenylmethanes Alternative Parents

  • N-methylpiperazines
  • Aralkylamines
  • Trialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Diphenylmethane
  • Aralkylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • N-alkylpiperazine (CHEBI:3994 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antiemetics
  • Histamine H1 Antagonists
  • Piperazine Derivatives

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility7.52e-02 g/LNot Available LogP3Not Available

    Predicted Properties

    Property Value Source Water Solubility0.075 mg/mLALOGPS logP3.55ALOGPS logP3.55ChemAxon logS-3.5ALOGPS pKa (Strongest Basic)8.51ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area6.48 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity84.93 m3·mol-1ChemAxon Polarizability31.53 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01176

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01176

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01176 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    6470 KEGG Compound ID

    C06930 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cyclizine NuGOwiki Link

    HMDB15307 Metagene Link

    HMDB15307 METLIN ID

    Not Available PubChem Compound

    6726 PDB ID

    Not Available ChEBI ID

    3994

    Product: Arglabin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in sulfotransferase activity
    Specific function:
    Sulfotransferase that utilizes 3-phospho-5-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
    Gene Name:
    SULT1E1
    Uniprot ID:
    P49888
    Molecular weight:
    35126.185
    References
    1. Bamforth KJ, Dalgliesh K, Coughtrie MW: Inhibition of human liver steroid sulfotransferase activities by drugs: a novel mechanism of drug toxicity? Eur J Pharmacol. 1992 May 1;228(1):15-21. [PubMed:1397064 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. 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. Leza JC, Lizasoain I, Lorenzo P: H1- and H2-histamine receptor blockers and opiate analgesia in mice. Methods Find Exp Clin Pharmacol. 1990 Dec;12(10):671-8. [PubMed:1983158 ]

    PMID: 10748721

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