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Identification
Name Trimeprazine
Accession Number DB01246 (APRD00258)
Type small molecule
Groups approved
Description

A phenothiazine derivative that is used as an antipruritic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • (+-)-Alimemazine
  • (+-)-Trimeprazine
  • Alimemazine
  • Alimemazine S,S-dioxide
  • Bayer 1219
  • Methylpromazine
  • Oxomemazin
  • Oxomemazina [INN-Spanish]
  • Oxomemazine
  • Oxomemazine [DCF:INN]
  • Oxomemazinum [INN-Latin]
  • Oxymemazine
  • Trimeperazine
  • Trimeprazine 5,5-dioxide
  • Trimeprazine hemi-(+)tartrate
  • Trimeprazine Tartrat
  • Trimeprazine Tartrate
Brand names
  • Alimezine
  • Dosegran
  • Doxergan
  • Dysedon
  • Imakol
  • Levoprome
  • Panectyl
  • Repeltin
  • Repetin
  • Temaril
  • Teralen
  • Theralene
  • Vallergan
Brand name mixtures
  • Vanectyl-P Tablets (Prednisolone + Trimeprazine Tartrate)
Categories
  • Antipruritics
  • Phenothiazine Derivatives
CAS number 84-96-8
Weight Average: 298.446
Monoisotopic: 298.150369404
Chemical Formula C18H22N2S
InChI Key InChIKey=ZZHLYYDVIOPZBE-UHFFFAOYSA-N
InChI
InChI=1S/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
Plain Text
IUPAC Name
dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
SMILES
CC(CN(C)C)CN1C2=C(SC3=C1C=CC=C3)C=CC=C2
Plain Text
Mass Spec show (7.8 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenothiazines
Substructures
  • Ethers
  • Phenothiazines
  • Aliphatic and Aryl Amines
  • Thiazines
  • Benzene and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Anilines
Pharmacology
Indication Used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).
Pharmacodynamics 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.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Allergan herbert skin care div allergan inc
  • Alpharma us pharmaceuticals division
  • Morton grove pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Panectyl 5 mg Tablet 0.37 USD tablet
Panectyl 2.5 mg Tablet 0.3 USD tablet
Patents Not Available
Properties
State solid
Melting point 68 oC
Experimental Properties
Property Value Source
water solubility 0.942 mg/L PhysProp
logP 4.6 PhysProp
pKa 9.05 Various sources
Predicted Properties
Property Value Source
water solubility 8.35e-03 g/l ALOGPS
logP 4.82 ALOGPS
logP 4.41 ChemAxon Molconvert
logS -4.55 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 6.48 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 93.37 ChemAxon Molconvert
polarizability 34.83 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07172 Link_out
PubChem Compound 5574 Link_out
PubChem Substance 46508449 Link_out
ChemSpider 5373 Link_out
BindingDB 50062261 Link_out
Therapeutic Targets Database DAP001077 Link_out
PharmGKB PA451781 Link_out
Drug Product Database 1926292 Link_out
ATC Codes
  • D04AA10
  • R06AD02
  • R06AD05
  • R06AD01
AHFS Codes
  • 04:04.12
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:47

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.