| 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 |
|
| Name |
Meclizine |
| Drug Type |
|
| 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 |
- Ancolan
- Ancolon
- Antivert
- Antivert/25
- Antivert/50
- Bonadettes
- Bonadoxin
- Bonamine
- Bonine
- Calmonal
- Chiclida
- Diadril
- Dramamine
- Dramamine II
- Histamethine
- Histamethizine
- Histametizine
- Histametizyne
- Itinerol
- Marex
- Meclicot
- Meclizine Hcl
- Meclozine
- Medivert
- Monamine
- Navicalm
- Neo-Istafene
- Neo-Suprimal
- Neo-Suprimel
- Parachloramine
- Peremesin
- Postafene
- Ravelon
- Sabari
- Sea-Legs
- Siguran
- Subari
- Suprimal
- Travelon
- Veritab
- Vomisseis
- Vomissels
|
| Brand Mixtures |
- Antivert Tab (Meclizine Hydrochloride + Nicotinic Acid)
|
| Chemical IUPAC Name |
1-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine |
| Chemical Formula |
C25H27ClN2 |
| Chemical 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  |
| PubChem Compound |
4034  |
| PubChem Substance |
9327  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA450338  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
00220442  |
| RxList Link |
http://www.rxlist.com/cgi/generic/mecliz.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Meclizine  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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 |
|
| 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  |
| Contraindications |
Show  |
| Interactions |
Show  |
| 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 |
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Phase 1 Metabolizing Enzymes |
- Monoamine oxidase type B (MAO-B)
|
| Targets |
- Histamine H1 receptor
|
|
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 |
|
| 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  |
| Target 1 UniProtKB/Swiss-Prot ID |
P35367  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
HRH1_HUMAN  |
| 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  |
| Target 1 GenAtlas ID |
HRH1  |
| Target 1 HGNC ID |
HGNC:5182  |
| Target 1 Chromosome Location |
3 |
| Target 1 Locus |
3p25 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- 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
]
|
| Target 1 Drug References |
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
|