Details of the Drug

General Information of Drug (ID: DMORSFB)

Drug Name

Chloroquine

Synonyms

Amokin; Aralen; Aralen HCl; Arechin; Arechine; Arequin; Arolen; Arthrochin; Artrichin; Avlochlor; Avloclor; Bemaco; Bemaphate; Bemasulph; Benaquin; Bipiquin; CU-01000012392-2; Capquin; Chemochin; Chingamin; Chloraquine; Chlorochin; Chlorochine; Chlorochinum; Chloroin; Chloroquin; Chloroquina; Chloroquine (USP/INN); Chloroquine (VAN); Chloroquine Bis-Phosphoric Acid; Chloroquine FNA (TN); Chloroquine [USAN:INN:BAN]; Chloroquine phosphate; Chloroquinium; Chloroquinum; Chloroquinum [INN-Latin]; Chlorquin; Cidanchin; Clorochina; Clorochina [DCIT]; Cloroquina; Cloroquina [INN-Spanish]; Cocartrit; Dawaquin (TN); Delagil; Dichinalex; Elestol; Gontochin; Gontochin phosphate; Heliopar; Imagon; Ipsen 225; Iroquine; Khingamin; Klorokin; Lapaquin; Malaquin; Malaquin (*Diphosphate*); Malaren; Malarex; Mesylith; Miniquine; Neochin; Nivachine; Nivaquine B; Pfizerquine; Quinachlor; Quinagamin; Quinagamine; Quinercyl; Quingamine; Quinilon; Quinoscan; RP 3377; RP-3377; Resochen; Resochin; Resochin (TN); Resoquina; Resoquine; Reumachlor; Reumaquin; Rivoquine; Ro 01-6014/N2; Ronaquine; Roquine; SN 6718; SN-7618; ST 21; ST 21 (pharmaceutical); Sanoquin; Silbesan;Siragan; Solprina; Sopaquin; Tanakan; Tanakene; Tresochin; Trochin; W 7618;WIN 244

Indication

Disease Entry	ICD 11	Status	REF
Coronavirus Disease 2019 (COVID-19)	1D6Y	Phase 3	[1]
Malaria	1F40-1F45	Withdrawn from market	[2]
Middle East Respiratory Syndrome (MERS)	1D64	Investigative	[3]
Severe acute respiratory syndrome (SARS)	1D65	Investigative	[4]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

319.9

Topological Polar Surface Area (xlogp)

4.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 65-128 mcg/L [5]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.5 h [5]
Bioavailability: The bioavailability of drug is 67-114% [5]
Clearance: The total plasma clearance of drug is 0.35-1 L/h/kg [5]
Elimination: 50% of a dose is recovered in the urine as unchanged chloroquine, with 10% of the dose recovered in the urine as desethylchloroquine [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 20 - 60 days [5]
Metabolism: The drug is metabolized via the CYP2C8 and CYP3A4 to N-desethylchloroquine [5]
Vd: The volume of distribution (Vd) of drug is 200-800 L/kg [5]

Chemical Identifiers

Formula: C18H26ClN3
IUPAC Name: 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
Canonical SMILES: CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
InChI: InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChIKey: WHTVZRBIWZFKQO-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2719
ChEBI ID: CHEBI:3638
CAS Number: 54-05-7
DrugBank ID: DB00608
TTD ID: D07QYQ
ACDINA ID: D00121

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	[6], [7]
HUMAN pH-dependent viral fusion/replication (pH-DVF/R)	TTD16BI	.	Inhibitor	[6], [7]

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

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT04360759) Chloroquine Outpatient Treatment Evaluation for HIV-Covid-19. U.S. National Institutes of Health.
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
4	Therapeutic options for the 2019 novel coronavirus (2019-nCoV). Nat Rev Drug Discov. 2020 Mar;19(3):149-150.
5	Clinical pharmacokinetics and metabolism of chloroquine. Focus on recent advancements. Clin Pharmacokinet. 1996 Oct;31(4):257-74. doi: 10.2165/00003088-199631040-00003.
6	Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Res. 2020 Mar;30(3):269-271.
7	Insights from nanomedicine into chloroquine efficacy against COVID-19. Nat Nanotechnol. 2020 Apr;15(4):247-249.