Drug Details

General Information of the Drug (ID: DR9044)
Name
Hydroxychloroquine
Synonyms
hydroxychloroquine; 118-42-3; Plaquenil; Oxichloroquine; Hidroxicloroquina; Hydroxychloroquinum; oxichlorochine; WIN 1258; Quensyl; 2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol; 7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline; Polirreumin; Oxychlorochin; CHEBI:5801; 2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol; 7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline; Oxichlorochinum; HYDROXY CHLOROQUINE; HCQ; 2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol; 7-Chloro-4-(5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl)aminoquinoline; 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol; 2-((4-((7-Chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol; NSC4375; Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-; MFCD00242707; Idrossiclorochina [DCIT]; Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-; Idrossiclorochina; 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol; Hidroxicloroquina [INN-Spanish]; Hydroxychloroquinum [INN-Latin]; Hydroxychloroquine [INN:BAN]; 2-[[4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol; 2-{N-[4-(7-Chloro-4-quinolylamino)pentyl]-N-ethylamino}ethanol; Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-; 2-({4-[(7-chloro(4-quinolyl))amino]pentyl}ethylamino)ethan-1-ol; 7-chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline; 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline; Polirreumin (TN); NCGC00159483-02; Hydroxychloroquine (INN); EINECS 204-249-8; BRN 0253894; Dolquine; Ethanol, 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]-; R-Hydroxychloroquine; Ercoquin (Salt/Mix); Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, sulfate (1:1); (+-)-hydroxychloroquine; Spectrum2_001238; Spectrum5_001697; (+/-)-hydroxychloroquine; SCHEMBL8170; CHEMBL1535; 5-22-10-00280 (Beilstein Handbook Reference); (.+/-.)-Hydroxychloroquine; DivK1c_000942; SPBio_001116; GTPL7198; DTXSID8023135; HMS502P04; KBio1_000942; Win 1258-2; NINDS_000942; 2-[4-[(7-chloro-4-quinolyl)amino]pentyl-ethyl-amino]ethanol; ALBB-022466; BCP30197; BDBM50467780; SBB012559; STL429829; AKOS015997886; CCG-208059; DB01611; DT-0016; HY-W031727; MCULE-6282304706; VZ36170; IDI1_000942; NCGC00159483-03; NCGC00159483-06; M566; ST072188; SY270913; SBI-0052759.P002; CS-0075751; FT-0627143; FT-0669455; FT-0669456; C07043; D08050; AB00053257_02; 118H423; Q421094; BRD-A99117172-065-01-6; BRD-A99117172-065-02-4; F2173-0553; 2-((4-(7-chloroquinolin-4-ylamino)pentyl)(ethyl)amino)ethanol; 2-[(4-[(7-Chloro-4-quinolinyl)amino]pentyl)(ethyl)amino]ethanol #; 2-[[4-[(7-Chloro-4-quinolyl)amino]pentyl](ethyl)amino]ethanol; 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]1-methylbutylamino]-quinoline; 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]1-methylbutylamino]quinoline; 7-Chloro-4-(4-(N-ethyl-N-.beta.-hydroxyethylamino)-1-methylbutylamino)quinoline; Oxichloroquine;Oxychlorochin;2-[[4-[(7-Chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol
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Molecular Type
Small molecule
Disease Malaria [ICD-11: 1F40] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-2 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
The bioavailability of drug is 45%-55%
Bioavailability
74% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 96 mL/min
Clearance
The drug present in the plasma can be removed from the body at the rate of 11 mL/min/kg
Elimination
40-50% of hydroxychloroquine is excreted renally, while only 16-21% of a dose is excreted in the urine as unchanged drug
Elimination
27% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 4 hours
Half-life
The concentration or amount of drug in body reduced by one-half in 850 hours
Metabolism
The drug is metabolized via the CYP3A4 to the active metabolite desethylhydroxychloroquine, as well as the inactive metabolites desethylchloroquine and bidesethylchloroquine
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 29.7725 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.57%
Vd
The volume of distribution (Vd) of drug is 5522 L from blood and 44257 L from plasma
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 700 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 200 mg/mL
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Formula
C18H26ClN3O
PubChem CID
3652
Canonical SMILES
CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO
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)
InChIKey
XXSMGPRMXLTPCZ-UHFFFAOYSA-N
CAS Number
CAS 118-42-3
ChEBI ID
CHEBI:5801
TTD Drug ID
D0OJ4L
DrugBank ID
DB01611
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Ivermectin      Streptomyces avermitilis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 HCQ and ivermectin may show a consequential and synergistic action if administered simultaneously both for chemoprophylaxis and treatment of COVID-19.
Target and Pathway
Target(s) Toll-like receptor 7 (TLR7)  Molecule Info  [3]
KEGG Pathway Toll-like receptor signaling pathway Click to Show/Hide
2 Measles
3 Influenza A
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Toll receptor signaling pathway Click to Show/Hide
Reactome Trafficking and processing of endosomal TLR Click to Show/Hide
2 TRAF6 mediated IRF7 activation in TLR7/8 or 9 signaling
3 TRAF6 mediated induction of NFkB and MAP kinases upon TLR7/8 or 9 activation
4 MyD88 dependent cascade initiated on endosome
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 Toll-Like Receptors Cascades
3 MyD88 dependent cascade initiated on endosome
4 Trafficking and processing of endosomal TLR
5 Regulation of toll-like receptor signaling pathway
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7198).
Reference 2 Hydroxychloroquine and ivermectin: A synergistic combination for COVID-19 chemoprophylaxis and treatment?. J Am Acad Dermatol. 2020 Jun;82(6):e221.
Reference 3 TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35.
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