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Identification
NameAlimemazine
Accession NumberDB01246  (APRD00258)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

A phenothiazine derivative that is used as an antipruritic. [PubChem]

Structure
Thumb
Synonyms
Alimemazine
Methylpromazine
Repeltin
Trimeprazine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Panectyl 2.5 Liq 2.5mg/5mlliquid2.5 mgoralAventis Pharma Inc1960-12-312003-07-22Canada
Panectyl Tab 2.5mgtablet2.5 mgoralErfa Canada 2012 Inc1959-12-31Not applicableCanada
Panectyl Tab 5mgtablet5 mgoralErfa Canada 2012 Inc1959-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AlimezineNot Available
NedeltranNot Available
PanectylNot Available
TheralenNot Available
TheraleneNot Available
VallerganNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Alimemazine tartrate
4330-99-8
Thumb
  • InChI Key: AJZJIYUOOJLBAU-RNKHSWPKSA-N
  • Monoisotopic Mass: 746.317176732
  • Average Mass: 746.978
DBSALT000183
Categories
UNII76H78MJJ52
CAS number84-96-8
WeightAverage: 298.446
Monoisotopic: 298.150369404
Chemical FormulaC18H22N2S
InChI KeyInChIKey=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
IUPAC Name
dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Benzenoid
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).
PharmacodynamicsTrimeprazine (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 actionTrimeprazine 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.
Related Articles
AbsorptionWell absorbed in the digestive tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9738
Blood Brain Barrier+0.9886
Caco-2 permeable+0.7965
P-glycoprotein substrateSubstrate0.6637
P-glycoprotein inhibitor IInhibitor0.6501
P-glycoprotein inhibitor IIInhibitor0.7613
Renal organic cation transporterNon-inhibitor0.5286
CYP450 2C9 substrateNon-substrate0.7739
CYP450 2D6 substrateSubstrate0.748
CYP450 3A4 substrateSubstrate0.5224
CYP450 1A2 substrateNon-inhibitor0.804
CYP450 2C9 inhibitorNon-inhibitor0.9195
CYP450 2D6 inhibitorInhibitor0.9381
CYP450 2C19 inhibitorNon-inhibitor0.8436
CYP450 3A4 inhibitorNon-inhibitor0.6702
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6487
Ames testNon AMES toxic0.7784
CarcinogenicityNon-carcinogens0.9034
BiodegradationNot ready biodegradable0.9968
Rat acute toxicity3.1217 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9819
hERG inhibition (predictor II)Inhibitor0.818
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidoral2.5 mg
Tabletoral2.5 mg
Tabletoral5 mg
Prices
Unit descriptionCostUnit
Panectyl 5 mg Tablet0.37USD tablet
Panectyl 2.5 mg Tablet0.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point68 °CPhysProp
boiling point150-175 °C at 3.00E-01 mm HgPhysProp
water solubility0.942 mg/LNot Available
logP4.71HANSCH,C ET AL. (1995)
pKa9.05SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00835 mg/mLALOGPS
logP4.82ALOGPS
logP4.41ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.37 m3·mol-1ChemAxon
Polarizability34.83 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.83 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR06AD01
AHFS Codes
  • 04:04.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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. 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:7713167 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on January 21, 2014 21:20