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Identification
NameAlimemazine
Accession NumberDB01246  (APRD00258)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA 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)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 Interactions
Drug
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Alimemazine.
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Alimemazine.
5'-Deoxy-5'-MethylthioadenosineThe serum concentration of Alimemazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.
AcebutololAlimemazine may increase the hypotensive activities of Acebutolol.
AlfentanilAlimemazine may increase the hypotensive activities of Alfentanil.
AlphacetylmethadolAlimemazine may increase the hypotensive activities of Alphacetylmethadol.
AlprenololAlimemazine may increase the hypotensive activities of Alprenolol.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum phosphateAluminum phosphate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmodiaquineThe serum concentration of Alimemazine can be increased when it is combined with Amodiaquine.
AmoxapineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Amoxapine.
AmphetamineAmphetamine may decrease the sedative activities of Alimemazine.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Alimemazine.
ArotinololAlimemazine may increase the hypotensive activities of Arotinolol.
ArtemetherThe serum concentration of Alimemazine can be increased when it is combined with Artemether.
ArtesunateThe serum concentration of Alimemazine can be increased when it is combined with Artesunate.
AtenololAlimemazine may increase the hypotensive activities of Atenolol.
AtovaquoneThe serum concentration of Alimemazine can be increased when it is combined with Atovaquone.
BefunololAlimemazine may increase the hypotensive activities of Befunolol.
BenzphetamineBenzphetamine may decrease the sedative activities of Alimemazine.
Benzylpenicilloyl PolylysineAlimemazine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Alimemazine.
BetaxololAlimemazine may increase the hypotensive activities of Betaxolol.
BevantololAlimemazine may increase the hypotensive activities of Bevantolol.
BezitramideAlimemazine may increase the hypotensive activities of Bezitramide.
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
BisoprololAlimemazine may increase the hypotensive activities of Bisoprolol.
BopindololAlimemazine may increase the hypotensive activities of Bopindolol.
BufuralolAlimemazine may increase the hypotensive activities of Bufuralol.
BupranololAlimemazine may increase the hypotensive activities of Bupranolol.
BuprenorphineAlimemazine may increase the hypotensive activities of Buprenorphine.
ButorphanolAlimemazine may increase the hypotensive activities of Butorphanol.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
CarfentanilAlimemazine may increase the hypotensive activities of Carfentanil.
CarteololAlimemazine may increase the hypotensive activities of Carteolol.
CarvedilolAlimemazine may increase the hypotensive activities of Carvedilol.
CeliprololAlimemazine may increase the hypotensive activities of Celiprolol.
ChloroquineThe serum concentration of Alimemazine can be increased when it is combined with Chloroquine.
ChlorphentermineChlorphentermine may decrease the sedative activities of Alimemazine.
CitalopramThe risk or severity of adverse effects can be increased when Alimemazine is combined with Citalopram.
ClomipramineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Clomipramine.
CodeineAlimemazine may increase the hypotensive activities of Codeine.
DapoxetineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Dapoxetine.
DapsoneThe serum concentration of Alimemazine can be increased when it is combined with Dapsone.
DextroamphetamineDextroamphetamine may decrease the sedative activities of Alimemazine.
DextromoramideAlimemazine may increase the hypotensive activities of Dextromoramide.
DextropropoxypheneAlimemazine may increase the hypotensive activities of Dextropropoxyphene.
DezocineAlimemazine may increase the hypotensive activities of Dezocine.
DihydrocodeineAlimemazine may increase the hypotensive activities of Dihydrocodeine.
DihydroetorphineAlimemazine may increase the hypotensive activities of Dihydroetorphine.
DihydromorphineAlimemazine may increase the hypotensive activities of Dihydromorphine.
DiphenoxylateAlimemazine may increase the hypotensive activities of Diphenoxylate.
DoxycyclineThe serum concentration of Alimemazine can be increased when it is combined with Doxycycline.
DPDPEAlimemazine may increase the hypotensive activities of DPDPE.
EscitalopramThe risk or severity of adverse effects can be increased when Alimemazine is combined with Escitalopram.
EsmololAlimemazine may increase the hypotensive activities of Esmolol.
EthylmorphineAlimemazine may increase the hypotensive activities of Ethylmorphine.
EtoperidoneThe risk or severity of adverse effects can be increased when Alimemazine is combined with Etoperidone.
EtorphineAlimemazine may increase the hypotensive activities of Etorphine.
FenfluramineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Fenfluramine.
FentanylAlimemazine may increase the hypotensive activities of Fentanyl.
FluoxetineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Fluoxetine.
FluvoxamineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Fluvoxamine.
HalofantrineThe serum concentration of Alimemazine can be increased when it is combined with Halofantrine.
HeroinAlimemazine may increase the hypotensive activities of Heroin.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Alimemazine.
HydrocodoneAlimemazine may increase the hypotensive activities of Hydrocodone.
HydromorphoneAlimemazine may increase the hypotensive activities of Hydromorphone.
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide may decrease the sedative activities of Alimemazine.
HydroxychloroquineThe serum concentration of Alimemazine can be increased when it is combined with Hydroxychloroquine.
IndalpineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Indalpine.
IndenololAlimemazine may increase the hypotensive activities of Indenolol.
KetobemidoneAlimemazine may increase the hypotensive activities of Ketobemidone.
LabetalolAlimemazine may increase the hypotensive activities of Labetalol.
LevobunololAlimemazine may increase the hypotensive activities of Levobunolol.
Levomethadyl AcetateAlimemazine may increase the hypotensive activities of Levomethadyl Acetate.
LevomilnacipranThe risk or severity of adverse effects can be increased when Alimemazine is combined with Levomilnacipran.
LevorphanolAlimemazine may increase the hypotensive activities of Levorphanol.
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Alimemazine.
LofentanilAlimemazine may increase the hypotensive activities of Lofentanil.
Lu AA21004The risk or severity of adverse effects can be increased when Alimemazine is combined with Lu AA21004.
LumefantrineThe serum concentration of Alimemazine can be increased when it is combined with Lumefantrine.
MagaldrateMagaldrate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium carbonateMagnesium carbonate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Alimemazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
MefloquineThe serum concentration of Alimemazine can be increased when it is combined with Mefloquine.
MephentermineMephentermine may decrease the sedative activities of Alimemazine.
MethadoneAlimemazine may increase the hypotensive activities of Methadone.
Methadyl AcetateAlimemazine may increase the hypotensive activities of Methadyl Acetate.
MethamphetamineMethamphetamine may decrease the sedative activities of Alimemazine.
MetipranololAlimemazine may increase the hypotensive activities of Metipranolol.
MetoprololAlimemazine may increase the hypotensive activities of Metoprolol.
MilnacipranThe risk or severity of adverse effects can be increased when Alimemazine is combined with Milnacipran.
MorphineAlimemazine may increase the hypotensive activities of Morphine.
NadololAlimemazine may increase the hypotensive activities of Nadolol.
NalbuphineAlimemazine may increase the hypotensive activities of Nalbuphine.
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Alimemazine.
NormethadoneAlimemazine may increase the hypotensive activities of Normethadone.
OlanzapineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Olanzapine.
OpiumAlimemazine may increase the hypotensive activities of Opium.
OxprenololAlimemazine may increase the hypotensive activities of Oxprenolol.
OxycodoneAlimemazine may increase the hypotensive activities of Oxycodone.
OxymorphoneAlimemazine may increase the hypotensive activities of Oxymorphone.
ParoxetineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Paroxetine.
PenbutololAlimemazine may increase the hypotensive activities of Penbutolol.
PentazocineAlimemazine may increase the hypotensive activities of Pentazocine.
PethidineAlimemazine may increase the hypotensive activities of Pethidine.
PhenterminePhentermine may decrease the sedative activities of Alimemazine.
PindololAlimemazine may increase the hypotensive activities of Pindolol.
PractololAlimemazine may increase the hypotensive activities of Practolol.
PrimaquineThe serum concentration of Alimemazine can be increased when it is combined with Primaquine.
ProguanilThe serum concentration of Alimemazine can be increased when it is combined with Proguanil.
PropranololAlimemazine may increase the hypotensive activities of Propranolol.
PyrimethamineThe serum concentration of Alimemazine can be increased when it is combined with Pyrimethamine.
QuinacrineThe serum concentration of Alimemazine can be increased when it is combined with Quinacrine.
QuinidineThe serum concentration of Alimemazine can be increased when it is combined with Quinidine.
QuinineThe serum concentration of Alimemazine can be increased when it is combined with Quinine.
RadicicolThe serum concentration of Alimemazine can be increased when it is combined with Radicicol.
RemifentanilAlimemazine may increase the hypotensive activities of Remifentanil.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Alimemazine.
SertralineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Sertraline.
SinefunginThe serum concentration of Alimemazine can be increased when it is combined with Sinefungin.
SotalolAlimemazine may increase the hypotensive activities of Sotalol.
SufentanilAlimemazine may increase the hypotensive activities of Sufentanil.
SulfadoxineThe serum concentration of Alimemazine can be increased when it is combined with Sulfadoxine.
SulfametopyrazineThe serum concentration of Alimemazine can be increased when it is combined with Sulfametopyrazine.
tafenoquineThe serum concentration of Alimemazine can be increased when it is combined with tafenoquine.
TapentadolAlimemazine may increase the hypotensive activities of Tapentadol.
ThiopentalThe risk or severity of adverse effects can be increased when Alimemazine is combined with Thiopental.
TimololAlimemazine may increase the hypotensive activities of Timolol.
TramadolAlimemazine may increase the hypotensive activities of Tramadol.
TrazodoneThe risk or severity of adverse effects can be increased when Alimemazine is combined with Trazodone.
TrimethoprimThe serum concentration of Alimemazine can be increased when it is combined with Trimethoprim.
VilazodoneThe risk or severity of adverse effects can be increased when Alimemazine is combined with Vilazodone.
VortioxetineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Vortioxetine.
ZimelidineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Zimelidine.
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23