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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:40
Primary Accession Number DB00737
Secondary Accession Number
  • APRD00354
Name Meclizine
Drug Type
  • Approved
  • Small Molecule
Description A histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]
Synonyms Not Available
Brand Names
  1. Ancolan
  2. Ancolon
  3. Antivert
  4. Antivert/25
  5. Antivert/50
  6. Bonadettes
  7. Bonadoxin
  8. Bonamine
  9. Bonine
  10. Calmonal
  11. Chiclida
  12. Diadril
  13. Dramamine
  14. Dramamine II
  15. Histamethine
  16. Histamethizine
  17. Histametizine
  18. Histametizyne
  19. Itinerol
  20. Marex
  21. Meclicot
  22. Meclizine Hcl
  23. Meclozine
  24. Medivert
  25. Monamine
  26. Navicalm
  27. Neo-Istafene
  28. Neo-Suprimal
  29. Neo-Suprimel
  30. Parachloramine
  31. Peremesin
  32. Postafene
  33. Ravelon
  34. Sabari
  35. Sea-Legs
  36. Siguran
  37. Subari
  38. Suprimal
  39. Travelon
  40. Veritab
  41. Vomisseis
  42. Vomissels
Brand Mixtures
  1. Antivert Tab (Meclizine Hydrochloride + Nicotinic Acid)
Chemical IUPAC Name 1-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine
Chemical Formula C25H27ClN2
Chemical Structure Structure
CAS Registry Number 569-65-3
InChI Identifier InChI=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 Key OCJYIGYOJCODJL-UHFFFAOYAY
KEGG Drug Not Available
KEGG Compound C07116 Link Image
PubChem Compound 4034 Link Image
PubChem Substance 9327 Link Image
ChEBI ID Not Available
PharmGKB ID PA450338 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00220442 Link Image
RxList Link http://www.rxlist.com/cgi/generic/mecliz.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Meclizine Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Morren, U.S. Pat. 2,709,169 (1955)
Average Molecular Weight 390.9480
Monoisotopic Molecular Weight 390.1863
State Solid
Melting Point Not Available
Experimental Water Solubility 0.1gm/100ml Source: PhysProp
Predicted Water Solubility 1.03e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 5.8 Source: PhysProp
Predicted LogP 5.59 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.58 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1=CC(CN2CCN(CC2)[C@H](C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1
Canonical SMILES CC1=CC(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)=CC=C1
Drug Category
  • Anti-Allergic Agents
  • Antiemetics
  • Antihistamines
  • Histamine H1 Antagonists
ATC Codes
AHFS Codes
  • 56:22.08
Indication For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
Pharmacology Meclizine, a piperazine-derivative H1-receptor antagonist similar to buclizine, cyclizine, and hydroxyzine, is used as an antivertigo/antiemetic agent. Meclizine is used in the management of nausea, vomiting, and dizziness associated with motion sickness and vertigo in diseases affecting the vestibular apparatus.
Mechanism of Action 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.
Absorption Well absorbed
Toxicity Symptoms of overdose include drowsiness and anticholinergic effects. LD50=mg/kg (orally in rat).
Protein Binding Not Available
Biotransformation Hepatic
Half Life 6 hours
Dosage Forms
Form Route
Tablet, chewable Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Rivastigmine Possible antagonism of action
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Monoamine oxidase type B (MAO-B)
Targets
  1. Histamine H1 receptor
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Monoamine oxidase type B (MAO-B)
Enzyme 1 Gene Name MAOB
Enzyme 1 SwissProt ID P27338 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P27338|AOFB_HUMAN Amine oxidase B 
SNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQKVKYVDLGGSYV
GPTQNRILRLAKELGLETYKVNEVERLIHHVKGKSYPFRGPFPPVWNPITYLDHNNFWRT
MDDMGREIPSDAPWKAPLAEEWDNMTMKELLDKLCWTESAKQLATLFVNLCVTAETHEVS
ALWFLWYVKQCGGTTRIISTTNGGQERKFVGGSGQVSERIMDLLGDRVKLERPVIYIDQT
RENVLVETLNHEMYEAKYVISAIPPTLGMKIHFNPPLPMMRNQMITRVPLGSVIKCIVYY
KEPFWRKKDYCGTMIIDGEEAPVAYTLDDTKPEGNYAAIMGFILAHKARKLARLTKEERL
KKLCELYAKVLGSLEALEPVHYEEKNWCEEQYSGGCYTTYFPPGILTQYGRVLRQPVDRI
YFAGTETATHWSGYMEGAVEAGERAAREILHAMGKIPEDEIWQSEPESVDVPAQPITTTF
LERHLPSVPGLLRLIGLTTIFSATALGFLAHKRGLLVRV
Drug Target 1 [top]
Target 1 ID 492
Target 1 Name Histamine H1 receptor
Target 1 Synonyms Not Available
Target 1 Gene Name HRH1
Target 1 Protein Sequence >Histamine H1 receptor 
MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLYAVRSERKLHT
VGNLYIVSLSVADLIVGAVVMPMNILYLLMSKWSLGRPLCLFWLSMDYVASTASIFSVFI
LCIDRYRSVQQPLRYLKYRTKTRASATILGAWFLSFLWVIPILGWNHFMQQTSVRREDKC
ETDFYDVTWFKVMTAIINFYLPTLLMLWFYAKIYKAVRQHCQHRELINRSLPSFSEIKLR
PENPKGDAKKPGKESPWEVLKRKPKDAGGGSVLKSPSQTPKEMKSPVVFSQEDDREVDKL
YCFPLDIVHMQAAAEGSSRDYVAVNRSHGQLKTDEQGLNTHGASEISEDQMLGDSQSFSR
TDSDTTTETAPGKGKLRSGSNTGLDYIKFTWKRLRSHSRQYVSGLHMNRERKAAKQLGFI
MAAFILCWIPYFIFFMVIAFCKNCCNEHLHMFTIWLGYINSTLNPLIYPLCNENFKKTFK
RILHIRS
Target 1 Number of Residues 495
Target 1 Molecular Weight 55785
Target 1 Theoretical pI 9.58
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-49
  • 64-83
  • 102-123
  • 146-165
  • 190-210
  • 419-438
  • 451-470
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 510296 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35367 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1464 bp 
ATGAGCCTCCCCAATTCCTCCTGCCTCTTAGAAGACAAGATGTGTGAGGGCAACAAGACC
ACTATGGCCAGCCCCCAGCTGATGCCCCTGGTGGTGGTCCTGAGCACTATCTGCTTGGTC
ACAGTAGGGCTCAACCTGCTGGTGCTGTATGCCGTACGGAGTGAGCGGAAGCTCCACACT
GTGGGGAACCTGTACATCGTCAGCCTCTCGGTGGCGGACTTGATCGTGGGTGCCGTCGTC
ATGCCTATGAACATCCTCTACCTGCTCATGTCCAAGTGGTCACTGGGCCGTCCTCTCTGC
CTCTTTTGGCTTTCCATGGACTATGTGGCCAGCACAGCGTCCATTTTCAGTGTCTTCATC
CTGTGCATTGATCGCTACCGCTCTGTCCAGCAGCCCCTCAGGTACCTTAAGTATCGTACC
AAGACCCGAGCCTCGGCCACCATTCTGGGGGCCTGGTTTCTCTCTTTTCTGTGGGTTATT
CCCATTCTAGGCTGGAATCACTTCATGCAGCAGACCTCGGTGCGCCGAGAGGACAAGTGT
GAGACAGACTTCTATGATGTCACCTGGTTCAAGGTCATGACTGCCATCATCAACTTCTAC
CTGCCCACCTTGCTCATGCTCTGGTTCTATGCCAAGATCTACAAGGCCGTACGACAACAC
TGCCAGCACCGGGAGCTCATCAATAGGTCCCTCCCTTCCTTCTCAGAAATTAAGCTGAGG
CCAGAGAACCCCAAGGGGGATGCCAAGAAACCAGGGAAGGAGTCTCCCTGGGAGGTTCTG
AAAAGGAAGCCAAAAGATGCTGGTGGTGGATCTGTCTTGAAGTCACCATCCCAAACCCCC
AAGGAGATGAAATCCCCAGTTGTCTTCAGCCAAGAGGATGATAGAGAAGTAGACAAACTC
TACTGCTTTCCACTTGATATTGTGCACATGCAGGCTGCGGCAGAGGGGAGTAGCAGGGAC
TATGTAGCCGTCAACCGGAGCCATGGCCAGCTCAAGACAGATGAGCAGGGCCTGAACACA
CATGGGGCCAGCGAGATATCAGAGGATCAGATGTTAGGTGATAGCCAATCCTTCTCTCGA
ACGGACTCAGATACCACCACAGAGACAGCACCAGGCAAAGGCAAATTGAGGAGTGGGTCT
AACACAGGCCTGGATTACATCAAGTTTACTTGGAAGAGGCTCCGCTCGCATTCAAGACAG
TATGTATCTGGGTTGCACATGAACCGCGAAAGGAAGGCCGCCAAACAGTTGGGTTTTATC
ATGGCAGCCTTCATCCTCTGCTGGATCCCTTATTTCATCTTCTTCATGGTCATTGCCTTC
TGCAAGAACTGTTGCAATGAACATTTGCACATGTTCACCATCTGGCTGGGCTACATCAAC
TCCACACTGAACCCCCTCATCTACCCCTTGTGCAATGAGAACTTCAAGAAGACATTCAAG
AGAATTCTGCATATTCGCTCCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH1 Link Image
Target 1 GenAtlas ID HRH1 Link Image
Target 1 HGNC ID HGNC:5182 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3p25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Fukui H, Fujimoto K, Mizuguchi H, Sakamoto K, Horio Y, Takai S, Yamada K, Ito S: Molecular cloning of the human histamine H1 receptor gene. Biochem Biophys Res Commun. 1994 Jun 15;201(2):894-901. [PubMed Link Image]
  2. De Backer MD, Gommeren W, Moereels H, Nobels G, Van Gompel P, Leysen JE, Luyten WH: Genomic cloning, heterologous expression and pharmacological characterization of a human histamine H1 receptor. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1601-8. [PubMed Link Image]
Target 1 Drug References
  1. 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. [PubMed Link Image]
  2. 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. [PubMed Link Image]
  3. 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. [PubMed Link Image]
  4. 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. [PubMed Link Image]
  5. 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. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.