Classification Term: 554

4-aminoquinolines (ontology term: CHEMONTID:0004537)

Organic compounds containing an amino group attached to the 4-position of a quinoline ring system." []

found 23 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Aminoquinolines and derivatives

Child Taxonomies: There is no child term of current ontology term.

Amodiaquine

4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

C20H22ClN3O (355.14513120000004)


Amodiaquine is only found in individuals that have used or taken this drug. It is a 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]The mechanism of plasmodicidal action of amodiaquine is not completely certain. 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. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function. P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BA - Aminoquinolines D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent

   

Chloroquine

N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine

C18H26ClN3 (319.1815146)


Chloroquine is only found in individuals that have used or taken this drug. It is a prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem]The mechanism of plasmodicidal action of chloroquine is not completely certain. 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. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell.During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals.Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products. P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BA - Aminoquinolines COVID info from Guide to PHARMACOLOGY, DrugBank, clinicaltrial, clinicaltrials, clinical trial, clinical trials D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D018501 - Antirheumatic Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Hydroxychloroquine

7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline

C18H26ClN3O (335.1764296)


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. P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BA - Aminoquinolines COVID info from Guide to PHARMACOLOGY, clinicaltrial, clinicaltrials, clinical trial, clinical trials D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D018501 - Antirheumatic Agents D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Desethylchloroquine

7-chloro-N-[5-(ethylamino)pentan-2-yl]quinolin-4-amine

C16H22ClN3 (291.1502162)


Desethylchloroquine is the major product of the stereoselective human metabolism of Chloroquine, used for the therapy and prevention of malaria.

   

desethylamodiaquine

4-((7-Chloro-4-quinolinyl)amino)-2-((ethylamino)methyl)phenol

C18H18ClN3O (327.1138328)


desethylamodiaquine is a metabolite of amodiaquine. Amodiaquine (trade names Camoquin, Flavoquine) is a 4-aminoquinoline compound related to chloroquine, used as an antimalarial and anti-inflammatory agent. Amodiaquine has been shown to be more effective than chloroquine in treating CRPF (chloroquine-resistant Plasmodium falciparum) malaria infections and may afford more protection than chloroquine when used as weekly prophylaxis. Amodiaquine, like chloroquine, is generally well tolerated. (Wikipedia)

   

Bosutinib

4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

C26H29Cl2N5O3 (529.1647344)


Bosutinib is a Bcr-Abl kinase inhibitor for the treatment of Philadelphia chromosome-positive (Ph+) chronic myelogenous leukemia (CML). Compared to other tyrosine kinase inhibitors, it has a more favourable hematologic toxicity profile. FDA approved on September 4, 2012 (DB06616). L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01E - Protein kinase inhibitors > L01EA - Bcr-abl tyrosine kinase inhibitors C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C155700 - BCR-ABL Inhibitor C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor

   

4-Aminoquinoline

1,4-dihydroquinolin-4-imine

C9H8N2 (144.0687448)


   

7-Chloro-N-[3-(2-nitroimidazol-1-yl)propyl]quinolin-4-amine

7-chloro-N-[3-(2-nitro-1H-imidazol-1-yl)propyl]quinolin-4-amine

C15H14ClN5O2 (331.0835974)


   

4-Amino-7-chloroquinoline

7-Chloro-4-aminoquinoline

C9H7ClN2 (178.0297732)


   

N-[4-[3-Chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide

N-[4-({3-chloro-4-[(pyridin-2-yl)methoxy]phenyl}amino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide

C30H29ClN6O3 (556.1989554)


   

Aminoquinol

[4-({7-chloro-2-[2-(2-chlorophenyl)ethenyl]-1,4-dihydroquinolin-4-ylidene}amino)pentyl]diethylamine

C26H31Cl2N3 (455.1894906)


   

Amopyroquine

4-[(7-chloroquinolin-4-yl)amino]-2-[(pyrrolidin-1-yl)methyl]phenol

C20H20ClN3O (353.12948200000005)


C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent

   

Didesethyl Chloroquine

N4-(7-chloroquinolin-4-yl)pentane-1,4-diamine

C14H18ClN3 (263.1189178)


   

Cletoquine

2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol

C16H22ClN3O (307.1451312)


C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent

   

Floctafenic acid

2-{[8-(trifluoromethyl)quinolin-4-yl]amino}benzoic acid

C17H11F3N2O2 (332.07725819999996)


   

floctafenine

2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)quinolin-4-yl]amino}benzoic acid

C20H17F3N2O4 (406.1140358)


   

Glafenine

4-(2-beta,gamma-Dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline

C19H17ClN2O4 (372.0876792)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent D002491 - Central Nervous System Agents > D000700 - Analgesics N - Nervous system > N02 - Analgesics

   

Trichomonacid

N-[5-(diethylamino)pentan-2-yl]-6-methoxy-2-[2-(4-nitrophenyl)ethenyl]quinolin-4-amine

C27H34N4O3 (462.26307740000004)


   

Losulazine

N-{4-[4-(4-fluorobenzenesulfonyl)piperazine-1-carbonyl]phenyl}-7-(trifluoromethyl)quinolin-4-amine

C27H22F4N4O3S (558.134867)


C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent

   

Naphthoquine

2-[(tert-butylamino)methyl]-4-[(7-chloroquinolin-4-yl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol

C24H28ClN3O (409.19207880000005)


   

N6-[2-[5-(Diethylamino)pentan-2-ylamino]-6-methyl-4-pyrimidinyl]-2-methylquinoline-4,6-diamine

N6-(2-{[5-(diethylamino)pentan-2-yl]amino}-6-methylpyrimidin-4-yl)-2-methylquinoline-4,6-diamine

C24H35N7 (421.295379)


NSC 23766 is a cell-permeable, reversible and specific inhibitor of Rac GTPase, used for cancer treatment.

   

Pelitinib

N-{4-[(3-chloro-4-fluorophenyl)imino]-3-cyano-7-ethoxy-1,4-dihydroquinolin-6-yl}-4-(dimethylamino)but-2-enimidate

C24H23ClFN5O2 (467.152422)


   

N-[4-(Benzylamino)-3-cyanoquinolin-2-yl]-4-methoxybenzamide

N-[4-(benzylamino)-3-cyanoquinolin-2-yl]-4-methoxybenzene-1-carboximidic acid

C25H20N4O2 (408.158618)