Sitamaquine
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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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- 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
- 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
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
- Yeates C: Sitamaquine (GlaxoSmithKline/Walter Reed Army Institute). Curr Opin Investig Drugs. 2002 Oct;3(10):1446-52. [Article]
- 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]
- External Links
- PubChem Compound
- 42548
- PubChem Substance
- 175426898
- ChemSpider
- 38806
- ChEMBL
- CHEMBL57004
- ZINC
- ZINC000001535009
- PharmGKB
- PA166115581
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Pneumocystis Jirovecii Pneumonia 1 2 Completed Treatment Visceral Leishmaniasis 1 1 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Pneumocystis Jirovecii Pneumonia 1
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 0.0134 mg/mL ALOGPS logP 5.11 ALOGPS logP 4.16 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 17.89 Chemaxon pKa (Strongest Basic) 10.33 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.39 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 107.91 m3·mol-1 Chemaxon Polarizability 42.88 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.987 Blood Brain Barrier + 0.9748 Caco-2 permeable + 0.5575 P-glycoprotein substrate Substrate 0.8682 P-glycoprotein inhibitor I Inhibitor 0.7545 P-glycoprotein inhibitor II Non-inhibitor 0.5399 Renal organic cation transporter Inhibitor 0.6236 CYP450 2C9 substrate Non-substrate 0.8455 CYP450 2D6 substrate Non-substrate 0.5231 CYP450 3A4 substrate Substrate 0.5889 CYP450 1A2 substrate Inhibitor 0.646 CYP450 2C9 inhibitor Non-inhibitor 0.9314 CYP450 2D6 inhibitor Inhibitor 0.8863 CYP450 2C19 inhibitor Non-inhibitor 0.8189 CYP450 3A4 inhibitor Non-inhibitor 0.9084 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.64 Ames test AMES toxic 0.8919 Carcinogenicity Non-carcinogens 0.8808 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7086 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7372 hERG inhibition (predictor II) Inhibitor 0.9307
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0019000000-79bf7cf0076af0c2d5e0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-e00e97417a333213c30c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0039000000-e1d9c7dd4bd344e14c66 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0129000000-af04dfba7336c256c616 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dr-8963000000-4f90b917066da33c8d56 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0930000000-ee4157efb90147dacecb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 215.4546818 predictedDarkChem Lite v0.1.0 [M-H]- 185.50069 predictedDeepCCS 1.0 (2019) [M+H]+ 215.7842818 predictedDarkChem Lite v0.1.0 [M+H]+ 187.86064 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.3416818 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.20357 predictedDeepCCS 1.0 (2019)
Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51