Dimetacrine

Identification

Generic Name
Dimetacrine
DrugBank Accession Number
DB08996
Background

Dimetacrine is also known as dimethacrine or acripamine. It is marketed under the names Istonil, Istonyl, Linostil, and Miroistonil. Dimetacrine is a tricyclic antidepressant (TCA) with imipramine-like effects used in Europe for the treatment of depression. Dimetacrine is no longer used in Japan.

Type
Small Molecule
Groups
Experimental, Withdrawn
Structure
Thumb
Weight
Average: 294.4338
Monoisotopic: 294.209598842
Chemical Formula
C20H26N2
Synonyms
  • 3-(9,9-dimethylacridin-10-yl)-N,N-dimethyl-propan-1-amine
  • Dimetacrine
  • Istonil
  • Istonyl
  • Linostil
  • Miroistonil

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Little is known about the pharmacology of dimetacrine.

Mechanism of action
TargetActionsOrganism
AAcetylcholinesterase
antagonist
Humans
Absorption

Not Available

Volume of distribution

The highest concentrations of dimetacrine were found at 1 hour after administration but at 3 hours in brain, heart, lung, liver, spleen, kidney, skeletal muscle and adipose tissue of testes. (Carried out in mice, PMID 5312397).

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Approximately 70% of the doses were excreted in urine and feces within 2 days after treatment. (PMID 5312397)

Half-life

Approximately 10 hours. (PMID 5312397)

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Dimetacrine may induce severe cardiac toxicity in overdose. This property is unique among the tricyclic antidepressants.

Pathways
Not Available
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 adverse effects can be increased when Dimetacrine is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Dimetacrine which could result in a higher serum level.
AcarboseDimetacrine may decrease the hypoglycemic activities of Acarbose.
AcebutololDimetacrine may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Dimetacrine is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Dimetacrine is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Dimetacrine is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Dimetacrine which could result in a higher serum level.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dimetacrine.
AcetohexamideDimetacrine may decrease the hypoglycemic activities of Acetohexamide.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dimetacrine bitartrateDVH164X0IF3759-07-7IIYKUJVECNNTEY-LREBCSMRSA-N
Dimetacrine tartrateNot AvailableNot AvailableNot applicable

Categories

ATC Codes
N06AA18 — Dimetacrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Benzoquinolines
Direct Parent
Acridines
Alternative Parents
Alkyldiarylamines / Benzenoids / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Acridine / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
O341NY501N
CAS number
4757-55-5
InChI Key
RYQOGSFEJBUZBX-UHFFFAOYSA-N
InChI
InChI=1S/C20H26N2/c1-20(2)16-10-5-7-12-18(16)22(15-9-14-21(3)4)19-13-8-6-11-17(19)20/h5-8,10-13H,9,14-15H2,1-4H3
IUPAC Name
[3-(9,9-dimethyl-9,10-dihydroacridin-10-yl)propyl]dimethylamine
SMILES
CN(C)CCCN1C2=CC=CC=C2C(C)(C)C2=CC=CC=C12

References

Synthesis Reference

GB933875

General References
  1. Ishitani R, Saito E, Kitagawa H: The pharmacological studies on dimetacrine. I. Studies on the absorption, distribution and excretion of H3-labeled dimetacrine in the rat. Jpn J Pharmacol. 1970 Sep;20(3):432-8. [Article]
KEGG Drug
D02565
KEGG Compound
C12959
PubChem Compound
94280
PubChem Substance
310264957
ChemSpider
85085
ChEBI
135233
ChEMBL
CHEMBL1328913
ZINC
ZINC000001482035
Wikipedia
Dimetacrine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3284454No1966-11-081986-11-08US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155-156U.S. Patent 3,284,454.
Predicted Properties
PropertyValueSource
Water Solubility0.0343 mg/mLALOGPS
logP4.96ALOGPS
logP4.42ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.52 m3·mol-1ChemAxon
Polarizability35.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Ishitani R, Sato T, Suga T, Kitagawa H: Studies on the ultrastructural distribution of H 3 -dimetacrine in rat cerebral cortex. Jpn J Pharmacol. 1972 Jun;22(3):313-23. [Article]

Drug created on June 16, 2014 19:04 / Updated on May 07, 2021 21:33