Quinacrine mustard

Identification

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Name
Quinacrine mustard
Accession Number
DB02240  (EXPT02733)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Quinacrine mustard dihydrochlorideRCB69HPY0X4213-45-0JETDZFFCRPFPDH-GGMCWBHBSA-N
Categories
UNII
8Y3YQP8GW6
CAS number
64046-79-3
Weight
Average: 468.85
Monoisotopic: 467.1297956
Chemical Formula
C23H28Cl3N3O
InChI Key
UKOBAUFLOGFCMV-UHFFFAOYSA-N
InChI
InChI=1S/C23H28Cl3N3O/c1-16(4-3-11-29(12-9-24)13-10-25)27-23-19-7-5-17(26)14-22(19)28-21-8-6-18(30-2)15-20(21)23/h5-8,14-16H,3-4,9-13H2,1-2H3,(H,27,28)
IUPAC Name
N-{5-[bis(2-chloroethyl)amino]pentan-2-yl}-6-chloro-2-methoxyacridin-9-amine
SMILES
COC1=CC2=C(NC(C)CCCN(CCCl)CCCl)C3=CC=C(Cl)C=C3N=C2C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypanothione reductase
inhibitor
Trypanosoma cruzi
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
20194
PubChem Substance
46507946
ChemSpider
19021
ChEBI
37595
ChEMBL
CHEMBL1190232
HET
QUM

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000967 mg/mLALOGPS
logP6.74ALOGPS
logP5.77ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.39 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.15 m3·mol-1ChemAxon
Polarizability50.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.974
Blood Brain Barrier+0.9449
Caco-2 permeable+0.5625
P-glycoprotein substrateSubstrate0.7776
P-glycoprotein inhibitor IInhibitor0.6048
P-glycoprotein inhibitor IIInhibitor0.9484
Renal organic cation transporterInhibitor0.8752
CYP450 2C9 substrateNon-substrate0.8106
CYP450 2D6 substrateNon-substrate0.6715
CYP450 3A4 substrateSubstrate0.6881
CYP450 1A2 substrateInhibitor0.7579
CYP450 2C9 inhibitorNon-inhibitor0.8644
CYP450 2D6 inhibitorInhibitor0.9084
CYP450 2C19 inhibitorNon-inhibitor0.7252
CYP450 3A4 inhibitorNon-inhibitor0.8047
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5951
Ames testAMES toxic0.7423
CarcinogenicityNon-carcinogens0.8758
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7935 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.645
hERG inhibition (predictor II)Inhibitor0.7439
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

Taxonomy

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
Chloroquinolines / Nitrogen mustard compounds / Anisoles / Alkyl aryl ethers / Pyridines and derivatives / Aryl chlorides / Secondary ketimines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
show 4 more
Substituents
Acridine / Haloquinoline / Chloroquinoline / Anisole / Nitrogen mustard / Alkyl aryl ether / Aryl chloride / Aryl halide / Benzenoid / Pyridine
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aminoacridines, nitrogen mustard (CHEBI:37595)

Targets

Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Trypanothione-disulfide reductase activity
Specific Function
Trypanothione is the parasite analog of glutathione; this enzyme is the equivalent of glutathione reductase.
Gene Name
TPR
Uniprot ID
P28593
Uniprot Name
Trypanothione reductase
Molecular Weight
53867.475 Da
References
  1. Saravanamuthu A, Vickers TJ, Bond CS, Peterson MR, Hunter WN, Fairlamb AH: Two interacting binding sites for quinacrine derivatives in the active site of trypanothione reductase: a template for drug design. J Biol Chem. 2004 Jul 9;279(28):29493-500. Epub 2004 Apr 21. [PubMed:15102853]
  2. Hossain MU, Oany AR, Ahmad SA, Hasan MA, Khan MA, Siddikey MA: Identification of potential inhibitor and enzyme-inhibitor complex on trypanothione reductase to control Chagas disease. Comput Biol Chem. 2016 Dec;65:29-36. doi: 10.1016/j.compbiolchem.2016.10.002. Epub 2016 Oct 7. [PubMed:27744094]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:30