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Showing drug card for Trimeprazine (DB01246)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:05:01
Primary Accession Number DB01246
Secondary Accession Number
  • APRD00258
Name Trimeprazine
Drug Type
  • Approved
  • Small Molecule
Description A phenothiazine derivative that is used as an antipruritic. [PubChem]
Synonyms
  1. (+-)-Alimemazine
  2. (+-)-Trimeprazine
  3. Alimemazine
  4. Alimemazine S,S-dioxide
  5. Bayer 1219
  6. Methylpromazine
  7. Oxomemazin
  8. Oxomemazina [INN-Spanish]
  9. Oxomemazine
  10. Oxomemazine [DCF:INN]
  11. Oxomemazinum [INN-Latin]
  12. Oxymemazine
  13. Trimeperazine
  14. Trimeprazine 5,5-dioxide
  15. Trimeprazine Tartrat
  16. Trimeprazine Tartrate
  17. Trimeprazine hemi-(+)tartrate
Brand Names
  1. Alimezine
  2. Dosegran
  3. Doxergan
  4. Dysedon
  5. Imakol
  6. Levoprome
  7. Panectyl
  8. Repeltin
  9. Repetin
  10. Temaril
  11. Teralen
  12. Theralene
  13. Vallergan
Brand Mixtures
  1. Vanectyl-P Tablets (Prednisolone + Trimeprazine Tartrate)
Chemical IUPAC Name N,N,2-trimethyl-3-phenothiazin-10-ylpropan-1-amine
Chemical Formula C18H22N2S
Chemical Structure Structure
CAS Registry Number 84-96-8
InChI Identifier InChI=1/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
InChI Key ZZHLYYDVIOPZBE-UHFFFAOYAQ
KEGG Drug Not Available
KEGG Compound C07172 Link Image
PubChem Compound 5574 Link Image
PubChem Substance 149788 Link Image
ChEBI ID Not Available
PharmGKB ID PA451781 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 01926292 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 298.4460
Monoisotopic Molecular Weight 298.1504
State Solid
Melting Point 68 oC
Experimental Water Solubility 0.942 mg/L Source: PhysProp
Predicted Water Solubility 8.35e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4.6 Source: PhysProp
Predicted LogP 4.82 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.55 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 9.05
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 C[C@H](CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12
Canonical SMILES CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12
Drug Category
  • Antipruritics
  • Phenothiazine Derivatives
ATC Codes
AHFS Codes
  • 04:04.12
Indication Used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).
Pharmacology Trimeprazine (also known as Alimemazine) is a tricyclic antihistamine, similar in structure to the phenothiazine antipsychotics, but differing in the ring-substitution and chain characteristics. Trimeprazine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, trimeprazine is not used clinically as an anti-psychotic. It acts as an anti-histamine, a sedative, and an anti-emetic (anti-nausea). Trimeprazine is used principally as an anti-emetic, to prevent motion sickness or as an anti-histamine in combination with other medications in cough and cold preparations. Tricyclic antihistamines are also structurally-related to the tricyclic antidepressants, explaining the antihistaminergic adverse effects of these two drug classes and also the poor tolerability profile of tricyclic H1-antihistamines.
Mechanism of Action Trimeprazine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Absorption Well absorbed in the digestive tract.
Toxicity Symptoms of overdose clumsiness or unsteadiness, seizures, severe drowsiness, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath, shuffling walk, tic-like (jerky) movements of head and face, trembling and shaking of hands, and insomnia.
Protein Binding Not Available
Biotransformation Hepatic
Half Life Not Available
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Pramlintide The anticholinergic effects of Trimeprazine may be enhanced by Pramlintide. Additive effects of reduced GI motility may occur. Pramlintide slows gastic emptying and should not be used with drugs that alter GI motility (e.g. anticholinergics). Consider alternative treatments or use caution during concomitant therapy.
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. 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
  • 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. Santos DE, Liu GJ, Takeuchi H: Blockers for excitatory effects of achatin-I, a tetrapeptide having a D-phenylalanine residue, on a snail neurone. Eur J Pharmacol. 1995 Jan 16;272(2-3):231-9. [PubMed Link Image]

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