Details of the Drug

General Information of Drug (ID: DMXZAL2)

Drug Name

Hydroxychloroquine

Synonyms

Hidroxicloroquina; Hidroxicloroquina [INN-Spanish]; Hydroxychlorochin; Gen-Hydroxychloroquine 200mg Tablets; HCQ; Hydroxychloroguine; Hydroxychloroquine (INN);Hydroxychloroquine [INN:BAN]; Hydroxychloroquine Sulfate (1:1) Salt; Hydroxychloroquinum; Hydroxychloroquinum [INN-Latin]; Idrossiclorochina; Idrossiclorochina [DCIT]; Oxichlorochinum; Oxichloroquine; Oxychlorochin; Oxychloroquine; Plaquenil (TN); Polirreumin; Polirreumin (TN); Quensyl; WIN 1258

Indication

Disease Entry	ICD 11	Status	REF
Malaria	1F40-1F45	Approved	[1]
Coronavirus Disease 2019 (COVID-19)	1D6Y	Phase 3	[2], [3]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

335.9

Topological Polar Surface Area (xlogp)

3.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-2 h [4]
Bioavailability: The bioavailability of drug is 45%-55% [4]
Clearance: The clearance of drug is 96 mL/min [5]
Elimination: 40-50% of hydroxychloroquine is excreted renally, while only 16-21% of a dose is excreted in the urine as unchanged drug [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 - 4 hours [6]
Metabolism: The drug is metabolized via the CYP3A4 to the active metabolite desethylhydroxychloroquine, as well as the inactive metabolites desethylchloroquine and bidesethylchloroquine [6]
Vd: The volume of distribution (Vd) of drug is 5522 L from blood and 44257 L from plasma [5]

Chemical Identifiers

Formula: C18H26ClN3O
IUPAC Name: 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
Canonical SMILES: CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO
InChI: 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

Cross-matching ID

PubChem CID: 3652
ChEBI ID: CHEBI:5801
CAS Number: 118-42-3
DrugBank ID: DB01611
TTD ID: D0UK3A
ACDINA ID: D00316

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
HUMAN glycosylation of host receptor (GHR)	TTZGK1R	.	Inhibitor	[7], [8]
HUMAN pH-dependent viral fusion/replication (pH-DVF/R)	TTD16BI	.	Inhibitor	[7], [8]
HUMAN toll-like receptor 7/9 signalling pathway (TLR7/9 pathway)	TT3A1EZ	.	Inhibitor	[9], [10]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	ClinicalTrials.gov (NCT04341727) Hydroxychloroquine,Hydroxychloroquine,Azithromycin in the Treatment of SARS CoV-2 Infection (WU352). U.S. National Institutes of Health.
3	Covid-19: US gives emergency approval to hydroxychloroquine despite lack of evidence. BMJ 2020. April. 01; 369:m1335
4	Clinical pharmacokinetics of ropinirole. Clin Pharmacokinet. 2000 Oct;39(4):243-54. doi: 10.2165/00003088-200039040-00001.
5	Furst DE: Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases. Lupus. 1996 Jun;5 Suppl 1:S11-5.
6	FDA Approved Drug Products: Hydroxychloroquine Oral Tablets
7	Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271.
8	Insights from nanomedicine into chloroquine efficacy against COVID-19. Nat Nanotechnol. 2020 Apr;15(4):247-249.
9	Mechanisms of action of hydroxychloroquine and chloroquine: implications for rheumatology. Nat Rev Rheumatol. 2020 Mar;16(3):155-166.
10	Use of Hydroxychloroquine and Chloroquine During the COVID-19 Pandemic: What Every Clinician Should Know. Ann Intern Med. 2020 Mar 31.