Sitamaquine

Identification

Generic Name
Sitamaquine
DrugBank Accession Number
DB04909
Background

Sitamaquine (WR-6026) is an orally active 8-aminoquinoline analog in development by the Walter Reed Army Institute, in collaboration with GlaxoSmithKline (formerly SmithKline Beecham), for the potential treatment of visceral leishmaniasis.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 343.5062
Monoisotopic: 343.262362693
Chemical Formula
C21H33N3O
Synonyms
  • Sitamaquine
External IDs
  • DRG-0140
  • WR 006026
  • WR 6026
  • WR-6026
  • WR6026

Pharmacology

Indication

Investigated for use/treatment in infectious and parasitic disease (unspecified).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

The mechanism of plasmodicidal action of sitamaquine is not completely understood. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.

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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
Aminoquinolines and derivatives
Alternative Parents
Methoxyanilines / Anisoles / Secondary alkylarylamines / Methylpyridines / Alkyl aryl ethers / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amine / Aminoquinoline / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Plasmodium

Chemical Identifiers

UNII
5AIJ4TGC6B
CAS number
57695-04-2
InChI Key
RVAKDGYPIVSYEU-UHFFFAOYSA-N
InChI
InChI=1S/C21H33N3O/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20/h11,13,15-16,22H,5-10,12,14H2,1-4H3
IUPAC Name
N-[6-(diethylamino)hexyl]-6-methoxy-4-methylquinolin-8-amine
SMILES
CCN(CC)CCCCCCNC1=CC(OC)=CC2=C(C)C=CN=C12

References

General References
  1. Yeates C: Sitamaquine (GlaxoSmithKline/Walter Reed Army Institute). Curr Opin Investig Drugs. 2002 Oct;3(10):1446-52. [Article]
  2. Sangraula H, Sharma KK, Rijal S, Dwivedi S, Koirala S: Orally effective drugs for kala-azar (visceral leishmaniasis): focus on miltefosine and sitamaquine. J Assoc Physicians India. 2003 Jul;51:686-90. [Article]
PubChem Compound
42548
PubChem Substance
175426898
ChemSpider
38806
ChEMBL
CHEMBL57004
ZINC
ZINC000001535009
PharmGKB
PA166115581

Clinical Trials

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
PropertyValueSource
Water Solubility0.0134 mg/mLALOGPS
logP5.11ALOGPS
logP4.16Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)17.89Chemaxon
pKa (Strongest Basic)10.33Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.39 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity107.91 m3·mol-1Chemaxon
Polarizability42.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier+0.9748
Caco-2 permeable+0.5575
P-glycoprotein substrateSubstrate0.8682
P-glycoprotein inhibitor IInhibitor0.7545
P-glycoprotein inhibitor IINon-inhibitor0.5399
Renal organic cation transporterInhibitor0.6236
CYP450 2C9 substrateNon-substrate0.8455
CYP450 2D6 substrateNon-substrate0.5231
CYP450 3A4 substrateSubstrate0.5889
CYP450 1A2 substrateInhibitor0.646
CYP450 2C9 inhibitorNon-inhibitor0.9314
CYP450 2D6 inhibitorInhibitor0.8863
CYP450 2C19 inhibitorNon-inhibitor0.8189
CYP450 3A4 inhibitorNon-inhibitor0.9084
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.64
Ames testAMES toxic0.8919
CarcinogenicityNon-carcinogens0.8808
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7086 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7372
hERG inhibition (predictor II)Inhibitor0.9307
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/MSsplash10-0006-0019000000-79bf7cf0076af0c2d5e0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-e00e97417a333213c30c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0039000000-e1d9c7dd4bd344e14c66
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0129000000-af04dfba7336c256c616
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-8963000000-4f90b917066da33c8d56
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0930000000-ee4157efb90147dacecb
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]-215.4546818
predicted
DarkChem Lite v0.1.0
[M-H]-185.50069
predicted
DeepCCS 1.0 (2019)
[M+H]+215.7842818
predicted
DarkChem Lite v0.1.0
[M+H]+187.86064
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.3416818
predicted
DarkChem Lite v0.1.0
[M+Na]+194.20357
predicted
DeepCCS 1.0 (2019)

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51