Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2020-02-26 21:41:49 UTC |
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HMDB ID | HMDB0015549 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hydroxychloroquine |
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Description | Hydroxychloroquine is only found in individuals that have used or taken this drug. It is a chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown. |
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Structure | |
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Synonyms | Value | Source |
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(+-)-Hydroxychloroquine | ChEBI | 2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol | ChEBI | 2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol | ChEBI | 7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline | ChEBI | 7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline | ChEBI | 7-Chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline | ChEBI | 7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline | ChEBI | Hidroxicloroquina | ChEBI | Hydroxychloroquinum | ChEBI | NSC4375 | ChEBI | Oxichlorochine | ChEBI | Oxichloroquine | ChEBI | Polirreumin | ChEBI | 7-Chloro-4-(4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino)quinoline | Generator | 7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinoline | Generator | 7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline | Generator | 7-Chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline | Generator | HCQ | HMDB | Oxychlorochin | HMDB | Hydroxychloroquine sulfate (1:1) salt | HMDB | Oxychloroquine | HMDB | Hydroxychlorochin | HMDB | Hydroxychloroquine sulfate | HMDB | Plaquenil | HMDB |
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Chemical Formula | C18H26ClN3O |
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Average Molecular Weight | 335.872 |
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Monoisotopic Molecular Weight | 335.176440176 |
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IUPAC Name | 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol |
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Traditional Name | hydroxychloroquine |
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CAS Registry Number | 118-42-3 |
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SMILES | CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1 |
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InChI Identifier | InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21) |
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InChI Key | XXSMGPRMXLTPCZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Quinolines and derivatives |
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Sub Class | Aminoquinolines and derivatives |
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Direct Parent | 4-aminoquinolines |
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Alternative Parents | |
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Substituents | - Chloroquinoline
- 4-aminoquinoline
- Haloquinoline
- Aminopyridine
- Secondary aliphatic/aromatic amine
- Aryl chloride
- Aryl halide
- Pyridine
- Benzenoid
- Heteroaromatic compound
- Tertiary aliphatic amine
- Tertiary amine
- 1,2-aminoalcohol
- Secondary amine
- Azacycle
- Alkanolamine
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Alcohol
- Primary alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 90 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.026 g/L | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fr-9262000000-58dde1657b5d6098be9b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00b9-9266000000-ea4f93631dd2ecfd327c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-3ad87c8e6d06353b69a1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-069a-3849000000-89ef84bf56d7c636c87a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-054n-9460000000-09312fdaefa09ffd4066 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0009000000-7d2e379f85931a4c8042 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1229000000-f952822a37d6efa233af | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-9641000000-8b6d466c2c58b3345281 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f6t-3972000000-7c193125680c0c9e276f | Spectrum |
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