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- Experimental, Withdrawn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
Structure for Dimetacrine (DB08996)
- 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
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Little is known about the pharmacology of dimetacrine.
- Mechanism of action
Target Actions Organism AAcetylcholinesterase antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Dimetacrine may induce severe cardiac toxicity in overdose. This property is unique among the tricyclic antidepressants.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Dimetacrine is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Dimetacrine which could result in a higher serum level. Acarbose Dimetacrine may decrease the hypoglycemic activities of Acarbose. Acebutolol Dimetacrine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of gastrointestinal bleeding can be increased when Dimetacrine is combined with Aceclofenac. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Dimetacrine bitartrate DVH164X0IF 3759-07-7 IIYKUJVECNNTEY-LREBCSMRSA-N Dimetacrine tartrate Not Available Not Available Not applicable
Categories
- ATC Codes
- N06AA18 — Dimetacrine
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Antidepressive Agents
- Antidepressive Agents, Tricyclic
- Central Nervous System Depressants
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Nervous System
- Neurotoxic agents
- Non-Selective Monoamine Reuptake Inhibitors
- Psychoanaleptics
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- 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
- General References
- 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]
- External Links
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US3284454 No 1966-11-08 1986-11-08 US 
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 155-156 U.S. Patent 3,284,454. - Predicted Properties
Property Value Source Water Solubility 0.0343 mg/mL ALOGPS logP 4.96 ALOGPS logP 4.42 Chemaxon logS -3.9 ALOGPS pKa (Strongest Basic) 9.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 105.52 m3·mol-1 Chemaxon Polarizability 35.87 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-6f20a9905617902994cb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-9fc897484d9e593cbd8c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6t-2090000000-0669ae95b28b4d9bebb5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-f0e59d69a773c665897f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0900-4590000000-b2070d2e12bb94b79eef Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-0590000000-7e3258c52d3ed1f0a374 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.1440081 predictedDarkChem Lite v0.1.0 [M-H]- 166.46823 predictedDeepCCS 1.0 (2019) [M+H]+ 183.7924081 predictedDarkChem Lite v0.1.0 [M+H]+ 168.82623 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.3239081 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.91939 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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 at June 16, 2014 19:04 / Updated at December 02, 2023 07:01