Identification
- Generic Name
- Quinacrine mustard
- DrugBank Accession Number
- DB02240
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Quinacrine mustard (DB02240)
- Weight
- Average: 468.85
Monoisotopic: 467.1297956 - Chemical Formula
- C23H28Cl3N3O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UTrypanothione reductase inhibitorTrypanosoma 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
- 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
Not Available
- 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.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Quinacrine mustard dihydrochloride RCB69HPY0X 4213-45-0 JETDZFFCRPFPDH-GGMCWBHBSA-N
Categories
- 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
- 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 / Alkyl aryl ether / Alkyl chloride / Alkyl halide / Amine / Anisole / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aminoacridines, nitrogen mustard (CHEBI:37595)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 8Y3YQP8GW6
- CAS number
- 64046-79-3
- 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
References
- General References
- Not Available
- External Links
Clinical Trials
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
Property Value Source Water Solubility 0.000967 mg/mL ALOGPS logP 6.74 ALOGPS logP 5.77 Chemaxon logS -5.7 ALOGPS pKa (Strongest Basic) 8.38 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.39 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 128.15 m3·mol-1 Chemaxon Polarizability 50.91 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.974 Blood Brain Barrier + 0.9449 Caco-2 permeable + 0.5625 P-glycoprotein substrate Substrate 0.7776 P-glycoprotein inhibitor I Inhibitor 0.6048 P-glycoprotein inhibitor II Inhibitor 0.9484 Renal organic cation transporter Inhibitor 0.8752 CYP450 2C9 substrate Non-substrate 0.8106 CYP450 2D6 substrate Non-substrate 0.6715 CYP450 3A4 substrate Substrate 0.6881 CYP450 1A2 substrate Inhibitor 0.7579 CYP450 2C9 inhibitor Non-inhibitor 0.8644 CYP450 2D6 inhibitor Inhibitor 0.9084 CYP450 2C19 inhibitor Non-inhibitor 0.7252 CYP450 3A4 inhibitor Non-inhibitor 0.8047 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5951 Ames test AMES toxic 0.7423 Carcinogenicity Non-carcinogens 0.8758 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7935 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.645 hERG inhibition (predictor II) Inhibitor 0.7439
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52