Meclizine (T3D2874)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-07-21 20:27:31 UTC
Update Date2014-12-24 20:25:52 UTC
Accession NumberT3D2874
Identification
Common NameMeclizine
ClassSmall Molecule
DescriptionMeclizine is only found in individuals that have used or taken this drug. It is a histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]Along with its actions as an antagonist at H1-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone.
Compound Type
  • Amine
  • Anti-Allergic Agent
  • Antiemetic
  • Drug
  • Histamine Antagonist
  • Histamine H1 Antagonist
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Antivert
Bonamine
Bonine
Chiclida
Dramamine
Meclicot
Meclozine
Navicalm
Nevidoxine
Postafen
Sea-Legs
Chemical FormulaC25H27ClN2
Average Molecular Mass390.948 g/mol
Monoisotopic Mass390.186 g/mol
CAS Registry Number569-65-3
IUPAC Name1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine
Traditional Namemeclizine
SMILESCC1=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1
InChI IdentifierInChI=1/C25H27ClN2/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23/h2-13,18,25H,14-17,19H2,1H3
InChI KeyInChIKey=OCJYIGYOJCODJL-UHFFFAOYNA-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
  • Benzylamine
  • Phenylmethylamine
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • N-alkylpiperazine
  • Toluene
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point217-224°C
Boiling PointNot Available
Solubility0.1gm/100ml
LogP5.8
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP5.59ALOGPS
logP6.39ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.39 m³·mol⁻¹ChemAxon
Polarizability44.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052r-1920000000-da1d25573308648315fa2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052r-1920000000-da1d25573308648315fa2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-1984000000-59561fa9a23e78a4a1c92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-66c42b235873c2a669762017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-02a85fbc5761853f587f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxr-0590000000-4633d1c1f89a98d9a6942017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0940000000-38b1d47fb87eb43db9bd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0910000000-0787c462628db94035672017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-9b3d5063cf1e4fd0ecda2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0390000000-10b11855a2539537e5af2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0gb9-0940000000-5877f50e2fa5ed23d00a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-0910000000-f238a0747a77e83f6f982021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0udi-0090000000-e341c3ea9d734714365b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0uxr-0590000000-0427308d1872c2c3ac2f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0090000000-d0c038e50dc835b3724b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-eaefbd608e93c9f354782016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0298000000-d9fdac408e87b3c2dc8c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1951000000-c1876845b9081d546d742016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-5a909f49cbcdca666c0e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0109000000-3c2989c5c8f415a9591f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9763000000-8429b322587128ad3a442016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-0049000000-3036ced88eac29b14a8d2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-cde3cef2a87633ad0dcd2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0980000000-73c4f8f44a2692d293c92021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-64dce0b80fb1d839019b2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0109000000-3b07e66adf588403a15b2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0036-3392000000-a48c57ae3e49c939767e2021-10-11View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ap0-1910000000-a39cf62803f22b3df2812014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral. Well absorbed
Mechanism of ToxicityAlong with its actions as an antagonist at H1-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone.
MetabolismHepatic Half Life: 6 hours
Toxicity ValuesLD50: 1600 mg/kg (oral) (1) LD50: 659 mg/kg (i.p.) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include drowsiness and anticholinergic effects.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00737
HMDB IDHMDB14875
PubChem Compound ID4034
ChEMBL IDCHEMBL1623
ChemSpider ID3894
KEGG IDC07116
UniProt IDNot Available
OMIM ID
ChEBI ID569632
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMeclizine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMeclizine
References
Synthesis Reference

U.S. Patent 2,709,169.

MSDST3D2874.pdf
General References
  1. Gillen C, Haurand M, Kobelt DJ, Wnendt S: Affinity, potency and efficacy of tramadol and its metabolites at the cloned human mu-opioid receptor. Naunyn Schmiedebergs Arch Pharmacol. 2000 Aug;362(2):116-21. [10961373 ]
  2. The Developmental Toxicity Of Meclizine Using The Frog Embryo Teratogenesis Assay-Xenopus. Andrea Wolfe, James Rayburn. Journal of the Alabama Academy of Science, Jan, 2001
  3. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Histamine H1 receptor
General Function:
Histamine receptor activity
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:
55783.61 Da
References
  1. Lima MC, Martins MA, Perez SA, Silva PM, Cordeiro RS, Vargaftig BB: Effect of azelastine on platelet-activating factor and antigen-induced pleurisy in rats. Eur J Pharmacol. 1991 May 17;197(2-3):201-7. [1680710 ]
  2. Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. [7513381 ]
  3. Martins MA, Pasquale CP, e Silva PM, Pires AL, Ruffie C, Rihoux JP, Cordeiro RS, Vargaftig BB: Interference of cetirizine with the late eosinophil accumulation induced by either PAF or compound 48/80. Br J Pharmacol. 1992 Jan;105(1):176-80. [1350745 ]
  4. Pasquale CP, e Silva PM, Lima MC, Diaz BL, Rihoux JP, Vargaftig BB, Cordeiro RS, Martins MA: Suppression by cetirizine of pleurisy triggered by antigen in actively sensitized rats. Eur J Pharmacol. 1992 Nov 13;223(1):9-14. [1362160 ]
  5. Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. [1678430 ]
Target Details
2. Nuclear receptor subfamily 1 group I member 3
General Function:
Zinc ion binding
Specific Function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular Weight:
39942.145 Da
References
  1. Huang W, Zhang J, Wei P, Schrader WT, Moore DD: Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR. Mol Endocrinol. 2004 Oct;18(10):2402-8. Epub 2004 Jul 22. [15272053 ]