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Identification
NameDimetacrine
Accession NumberDB08996
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

Dimetacrine (Istonil, Istonyl, Linostil, Miroistonil), also known as dimethacrine and acripramine, is a tricyclic antidepressant (TCA) with imipramine-like effects used in Europe and formerly in Japan for the treatment of depression.

Structure
Thumb
Synonyms
3-(9,9-dimethylacridin-10-yl)-N,N-dimethyl-propan-1-amine
Dimetacrine
Istonil
Istonyl
Linostil
Miroistonil
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dimetacrine bitartrate
ThumbNot applicableDBSALT001096
Dimetacrine tartrate
ThumbNot applicableDBSALT001095
Categories
UNIIO341NY501N
CAS number4757-55-5
WeightAverage: 294.4338
Monoisotopic: 294.209598842
Chemical FormulaC20H26N2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Alkyldiarylamine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsLittle is known about the pharmacology of dimetacrine.
Mechanism of actionNot Available
Related Articles
AbsorptionNot 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 bindingNot Available
MetabolismNot Available
Route of eliminationApproximately 70% of the doses were excreted in urine and feces within 2 days after treatment. (PMID 5312397)
Half lifeApproximately 10 hours. (PMID 5312397)
ClearanceNot Available
ToxicityDimetacrine may induce severe cardiac toxicity in overdose. This property is unique among the tricyclic antidepressants.
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 AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US3284454 No1966-11-081986-11-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point155-156U.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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference
  1. http://worldwide.espacenet.com/publicationDetails/biblio?CC=GB&NR=933875&KC=&FT=E&locale=en_EP
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. [PubMed:5312397 ]
External Links
ATC CodesN06AA18
AHFS CodesNot Available
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:
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
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. [PubMed:4539395 ]
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Drug created on June 16, 2014 13:04 / Updated on January 22, 2015 14:38