1. Hydroxychlorochin
2. Hydroxychloroquine Sulfate
3. Hydroxychloroquine Sulfate (1:1) Salt
4. Oxychlorochin
5. Oxychloroquine
6. Plaquenil
1. 118-42-3
2. Plaquenil
3. Oxichloroquine
4. Polirreumin
5. Hidroxicloroquina
6. Hydroxychloroquinum
7. Oxichlorochine
8. Win 1258
9. 2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol
10. 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol
11. 7-chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline
12. Oxychlorochin
13. Chebi:5801
14. 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
15. 2-(n-(4-(7-chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol
16. 7-chloro-4-(4-(n-ethyl-n-beta-hydroxyethylamino)-1-methylbutylamino)quinoline
17. Hydroxychloroquine (inn)
18. Oxichlorochinum
19. 4qwg6n8qkh
20. Hcq
21. 2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
22. 7-chloro-4-(5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl)aminoquinoline
23. Nsc4375
24. 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
25. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-
26. Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-
27. Mfcd00242707
28. Idrossiclorochina [dcit]
29. Idrossiclorochina
30. Hidroxicloroquina [inn-spanish]
31. Hydroxychloroquinum [inn-latin]
32. Hydroxychloroquine [inn]
33. Hydroxychloroquine [inn:ban]
34. 2-[[4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
35. 2-{n-[4-(7-chloro-4-quinolylamino)pentyl]-n-ethylamino}ethanol
36. Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-
37. 7-chloro-4-[4-(n-ethyl-n-beta-hydroxyethylamino)-1-methylbutylamino]quinoline
38. 7-chloro-4-[5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl]aminoquinoline
39. Polirreumin (tn)
40. Ncgc00159483-02
41. Einecs 204-249-8
42. Hydroxy Chloroquine
43. Unii-4qwg6n8qkh
44. Brn 0253894
45. Dolquine
46. Ethanol, 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]-
47. R-hydroxychloroquine
48. Ercoquin (salt/mix)
49. Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, Sulfate (1:1)
50. (+-)-hydroxychloroquine
51. Spectrum2_001238
52. Spectrum5_001697
53. Z0188
54. (+/-)-hydroxychloroquine
55. Schembl8170
56. Chembl1535
57. 5-22-10-00280 (beilstein Handbook Reference)
58. (.+/-.)-hydroxychloroquine
59. Divk1c_000942
60. Spbio_001116
61. Hydroxychloroquine [mi]
62. Gtpl7198
63. Dtxsid8023135
64. Hms502p04
65. Kbio1_000942
66. Hydroxychloroquine [vandf]
67. Win 1258-2
68. Ninds_000942
69. 2-[4-[(7-chloro-4-quinolyl)amino]pentyl-ethyl-amino]ethanol
70. Hydroxychloroquine [who-dd]
71. 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl](ethyl)amino]ethanol
72. Albb-022466
73. Bcp30197
74. 2-({4-[(7-chloro(4-quinolyl))amino]pentyl}ethylamino)ethan-1-ol
75. Bdbm50467780
76. Stl429829
77. Akos015997886
78. At13123
79. Ccg-208059
80. Db01611
81. Dt-0016
82. Hy-w031727
83. Sb73036
84. Idi1_000942
85. Ncgc00159483-03
86. Ncgc00159483-06
87. Sy270913
88. Sbi-0052759.p002
89. Cs-0075751
90. Ft-0627143
91. Ft-0669455
92. Ft-0669456
93. C07043
94. D08050
95. En300-122642
96. Ab00053257_02
97. 118h423
98. Q421094
99. Brd-a99117172-065-01-6
100. Brd-a99117172-065-02-4
101. F2173-0553
102. 2-((4-(7-chloroquinolin-4-ylamino)pentyl)(ethyl)amino)ethanol
103. 2-[(4-[(7-chloro-4-quinolinyl)amino]pentyl)(ethyl)amino]ethanol #
104. 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]1-methylbutylamino]-quinoline
105. 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]1-methylbutylamino]quinoline
106. (+/-)-2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol
107. 7-chloro-4-(4-(n-ethyl-n-.beta.-hydroxyethylamino)-1-methylbutylamino)quinoline
108. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethyl)amino-, (+/-)-
109. Oxichloroquine;oxychlorochin;2-[[4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
| Molecular Weight | 335.9 g/mol |
|---|---|
| Molecular Formula | C18H26ClN3O |
| XLogP3 | 3.6 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 9 |
| Exact Mass | g/mol |
| Monoisotopic Mass | g/mol |
| Topological Polar Surface Area | 48.4 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Complexity | 331 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Hydroxychloroquine is indicated for the prophylaxis of malaria where chloroquine resistance is not reported, treatment of uncomplicated malaria (caused by _P. falciparum_, _P. malariae_, _P. ovale_, or _P. vivax_), chronic discoid lupus erythematosus, systemic lupus erythematosus, acute rheumatoid arthritis, and chronic rheumatoid arthritis.
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
Antimalarials
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)
Antirheumatic Agents
Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)
P01BA02
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
P - Antiparasitic products, insecticides and repellents
P01 - Antiprotozoals
P01B - Antimalarials
P01BA - Aminoquinolines
P01BA02 - Hydroxychloroquine
Absorption
Hydroxychloroquine is 67-74% bioavailable. Bioavailability of the R and S enantiomers were not significantly different. Following a 200mg oral dose, hydroxychloroquine reached a Cmax of 129.6ng/mL with a Tmax of 3.26h in the blood and a Cmax of 50.3ng/mL with a Tmax of 3.74h in the plasma. Following 155mg and 310mg intravenous doses, Cmax in the blood ranged from 1161-2436ng/mL with an average of 1918ng/mL.
Route of Elimination
40-50% of hydroxychloroquine is excreted renally, while only 16-21% of a dose is excreted in the urine as unchanged drug. 5% of a dose is sloughed off in skin and 24-25% is eliminated through the feces.
Volume of Distribution
Hydroxychloroquine has a volume of distribution of 5522L from blood and 44,257L from plasma.
Clearance
The clearance of hydroxychloroquine is 96mL/min.
Hydroxychloroquine is N-dealkylated by CYP3A4 to the active metabolite desethylhydroxychloroquine, as well as the inactive metabolites desethylchloroquine and bidesethylchloroquine. Desethylhydroxychloroquine is the major metabolite.
Partially hepatic, to active de-ethylated metabolites. Half Life: Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
Oral hydroxychloroquine has an absorption half life of 3-4 hours. A 200mg oral dose of hydroxychloroquine has a half life of 537 hours or 22.4 days in blood, and 2963 hours or 123.5 days in plasma. A 155mg intravenous dose has a half life of 40 days.
The exact mechanisms of hydroxychloroquine are unknown. It has been shown that hydroxychloroquine accumulates in the lysosomes of the malaria parasite, raising the pH of the vacuole. This activity interferes with the parasite's ability to proteolyse hemoglobin, preventing the normal growth and replication of the parasite. Hydroxychloroquine can also interfere with the action of parasitic heme polymerase, allowing for the accumulation of the toxic product beta-hematin. Hydroxychloroquine accumulation in human organelles also raise their pH, which inhibits antigen processing, prevents the alpha and beta chains of the major histocompatibility complex (MHC) class II from dimerizing, inhibits antigen presentation of the cell, and reduces the inflammatory response. Elevated pH in the vesicles may alter the recycling of MHC complexes so that only the high affinity complexes are presented on the cell surface. Self peptides bind to MHC complexes with low affinity and so they will be less likely to be presented to autoimmune T cells. Hydroxychloroquine also reduces the release of cytokines like interleukin-1 and tumor necrosis factor, possibly through inhibition of Toll-like receptors. The raised pH in endosomes, prevent virus particles (such as SARS-CoV and SARS-CoV-2) from utilizing their activity for fusion and entry into the cell. Hydroxychloroquine inhibits terminal glycosylation of ACE2, the receptor that SARS-CoV and SARS-CoV-2 target for cell entry. ACE2 that is not in the glycosylated state may less efficiently interact with the SARS-CoV-2 spike protein, further inhibiting viral entry.
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