Alimemazine

Identification

Summary

Alimemazine is an antihistamine agent used to prevent and relieve allergic conditions which cause pruritus and other allergic skin conditions, including urticaria.

Brand Names
Panectyl
Generic Name
Alimemazine
DrugBank Accession Number
DB01246
Background

A phenothiazine derivative that is used as an antipruritic.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 298.446
Monoisotopic: 298.150369404
Chemical Formula
C18H22N2S
Synonyms
  • Alimemazina
  • Alimemazine
  • Alimemazinum
  • Methylpromazine
  • Trimeprazine
External IDs
  • Bayer 1219
  • BAYER-1219
  • RP 6549
  • RP-6549

Pharmacology

Indication

Used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions).

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCough••••••••••••
Treatment ofPruritus••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
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

Adverse Effects
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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.

Pathways
PathwayCategory
Alimemazine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Alimemazine is combined with 1,2-Benzodiazepine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Alimemazine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Alimemazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Alimemazine.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Alimemazine.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may potentiate the CNS depressant effects of alimemazine/trimeprazine.
  • Take after a meal. Taking alimemazine/trimeprazine after eating may reduce drowsiness by allowing for more gradual absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Alimemazine tartrate362NW1LD6Z4330-99-8AJZJIYUOOJLBAU-RNKHSWPKSA-N
International/Other Brands
Alimezine / Nedeltran / Repeltin / Theralen / Theralene / Vallergan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PanectylTablet5 mgOralSearchlight Pharma Inc1959-12-31Not applicableCanada flag
PanectylTablet2.5 mgOralSearchlight Pharma Inc1959-12-31Not applicableCanada flag
Panectyl 2.5 Liq 2.5mg/5mlLiquid2.5 mg / 5 mLOralAventis Pharma Ltd.1960-12-312003-07-22Canada flag

Categories

ATC Codes
R06AD01 — Alimemazine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines (CHEBI:9725)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
76H78MJJ52
CAS number
84-96-8
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0015376
KEGG Drug
D07125
KEGG Compound
C07172
PubChem Compound
5574
PubChem Substance
46508449
ChemSpider
5373
BindingDB
50062261
RxNav
10825
ChEBI
9725
ChEMBL
CHEMBL829
Therapeutic Targets Database
DAP001077
PharmGKB
PA164744009
Wikipedia
Alimemazine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Emcure Pharmaceuticals Ltd.
Dosage Forms
FormRouteStrength
TabletOral2.5 mg
TabletOral5 mg
LiquidOral2.5 mg / 5 mL
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)68 °CPhysProp
boiling point (°C)150-175 °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-4.6ALOGPS
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 RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (7.83 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-08fr-7190000000-0f8a5eefc8992f88c42e
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9010000000-3652afb69d877d9e3ef5
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a2
GC-MS Spectrum - CI-BGC-MSsplash10-0002-1192000000-93fd466d9dd2ccc3c679
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udj-2960000000-969a98d7684c36971aba
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4m-9170000000-1e604a60c25150b1b0a6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-41ab5d7b1386f78fe37e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0290000000-91c0334936e5aa26f71b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-8190000000-550655b43beb5e46f6e1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-0980000000-23a9576b474f0fcbdefe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.1774952
predicted
DarkChem Lite v0.1.0
[M-H]-160.59222
predicted
DeepCCS 1.0 (2019)
[M+H]+182.1885952
predicted
DarkChem Lite v0.1.0
[M+H]+162.95021
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.9923952
predicted
DarkChem Lite v0.1.0
[M+Na]+169.04338
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
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. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48