NAV

9-amino-n-[3-(dimethylamino)propyl]acridine-4-carboxamide

Identification

Generic Name
9-amino-n-[3-(dimethylamino)propyl]acridine-4-carboxamide
DrugBank Accession Number
DB02842
Background

9-amino-n-[3-(dimethylamino)propyl]acridine-4-carboxamide is an inactive derivative of the antitumour agents N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) and 9-amino-DACA.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 322.4042
Monoisotopic: 322.179361346
Chemical Formula
C19H22N4O
Synonyms
  • 9-amino-N-(3-dimethylaminopropyl)acridine-4-carboxamide
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDNA
intercalation
Humans
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
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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

Categories

Drug Categories
Not Available
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
Quinoline carboxamides / 4-aminoquinolines / Aminopyridines and derivatives / Benzenoids / Heteroaromatic compounds / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Azacyclic compounds / Primary amines
show 4 more
Substituents
4-aminoquinoline / Acridine / Amine / Amino acid or derivatives / Aminopyridine / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxamide group
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
0LY4HYL6F8
CAS number
Not Available
InChI Key
VNWAULKXOPRJEL-UHFFFAOYSA-N
InChI
InChI=1S/C19H22N4O/c1-23(2)12-6-11-21-19(24)15-9-5-8-14-17(20)13-7-3-4-10-16(13)22-18(14)15/h3-5,7-10H,6,11-12H2,1-2H3,(H2,20,22)(H,21,24)
IUPAC Name
9-amino-N-[3-(dimethylamino)propyl]acridine-4-carboxamide
SMILES
CN(C)CCCNC(=O)C1=CC=CC2=C(N)C3=C(C=CC=C3)N=C12

References

General References
Not Available
PubChem Compound
150238
PubChem Substance
46505229
ChemSpider
132441
BindingDB
50004358
ChEMBL
CHEMBL287038
ZINC
ZINC000005957683
PDBe Ligand
7AD
PDB Entries
1rqy

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0776 mg/mLALOGPS
logP2.37ALOGPS
logP1.83Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.74Chemaxon
pKa (Strongest Basic)9.33Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area71.25 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity97.62 m3·mol-1Chemaxon
Polarizability37.12 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9876
Blood Brain Barrier+0.9152
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.7298
P-glycoprotein inhibitor INon-inhibitor0.7549
P-glycoprotein inhibitor IINon-inhibitor0.5971
Renal organic cation transporterNon-inhibitor0.5216
CYP450 2C9 substrateNon-substrate0.861
CYP450 2D6 substrateNon-substrate0.5248
CYP450 3A4 substrateSubstrate0.6456
CYP450 1A2 substrateInhibitor0.7153
CYP450 2C9 inhibitorNon-inhibitor0.9086
CYP450 2D6 inhibitorNon-inhibitor0.5997
CYP450 2C19 inhibitorNon-inhibitor0.8901
CYP450 3A4 inhibitorNon-inhibitor0.6871
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.909
Ames testAMES toxic0.5819
CarcinogenicityNon-carcinogens0.8817
BiodegradationNot ready biodegradable0.9916
Rat acute toxicity2.5730 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9765
hERG inhibition (predictor II)Inhibitor0.8477
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/MSsplash10-00di-0059000000-40836a966f61e47ad541
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1009000000-7034bb775137f723d4dd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0091000000-c31bef107562f69385e7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dj-7269000000-567970c6b8e9cd646284
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-5390000000-f53f0070681505174e4f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-7970000000-e88c13f76dea4ce8a02b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.9237789
predicted
DarkChem Lite v0.1.0
[M-H]-178.25302
predicted
DeepCCS 1.0 (2019)
[M+H]+186.3477789
predicted
DarkChem Lite v0.1.0
[M+H]+180.61102
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.9111789
predicted
DarkChem Lite v0.1.0
[M+Na]+186.9772
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
Actions
Intercalation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Adams A, Guss JM, Denny WA, Wakelin LP: Crystal structure of 9-amino-N-[2-(4-morpholinyl)ethyl]-4-acridinecarboxamide bound to d(CGTACG)2: implications for structure-activity relationships of acridinecarboxamide topoisomerase poisons. Nucleic Acids Res. 2002 Feb 1;30(3):719-25. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52