Drug Details

General Information of the Drug (ID: DR1182)
Name
Chloroquine
Synonyms
chloroquine; 54-05-7; Aralen; Chlorochin; Chloraquine; Artrichin; Chloroquinium; Chloroquina; Reumachlor; Capquin; Chemochin; Chlorquin; Clorochina; Malaquin; Arthrochin; Bemasulph; Benaquin; Bipiquin; Chingamin; Cidanchin; Cocartrit; Dichinalex; Gontochin; Heliopar; Iroquine; Klorokin; Lapaquin; Mesylith; Pfizerquine; Quinachlor; Quinercyl; Quinilon; Quinoscan; Sanoquin; Silbesan; Solprina; Sopaquin; Tresochin; Amokin; Bemaco; Elestol; Imagon; Malaren; Malarex; Neochin; Roquine; Siragan; Trochin; Nivaquine B; Bemaphate; Resoquine; Nivaquine; Chlorochine; Chloroquinum; Cloroquina; Quingamine; Avloclor; Resochin; Ronaquine; Khingamin; N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine; Avlochlor; Nivachine; Quinagamin; Quinagamine; Resochen; Resoquina; Reumaquin; Arechin; Delagil; Tanakan; WIN 244; 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-; RP 3377; W 7618; Chloroin; Miniquine; Rivoquine; Tanakene; Arolen; 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline; CHEBI:3638; Chloroquine free base; N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine; Gontochin phosphate; CHEMBL76; SN 6718; 54-05-7 (free base); Ipsen 225; Chlorochinum; N(sup 4)-(7-Chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-1,4-pentanediamine; MFCD00024009; NSC187208; NSC-187208; SN 7618; Chloroquine (VAN); Clorochina [DCIT]; 7-Chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline; 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine; Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-; 3377 RP; SN-7618; 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-; ST 21 (pharmaceutical); Chloroquinum [INN-Latin]; Cloroquina [INN-Spanish]; 3377 RP opalate; Chloroquin; Quinoline, 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]-; N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine; ST 21; (+-)-Chloroquine; NSC14050; CCRIS 3439; HSDB 3029; Chloroquine (USP/INN); EINECS 200-191-2; {4-[(7-chloro(4-quinolyl))amino]pentyl}diethylamine; Malaquin (*Diphosphate*); NSC 187208; BRN 0482809; Cloroquine; Chloroquine [USP:INN:BAN]; Chloroquine, 17; Chloroquine-[d4]; 4,7-Dichloroquine; {4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine; Arechin (Salt/Mix); Delagil (Salt/Mix); Tanakan (Salt/Mix); 1246815-14-4; RP-3377; Bemaphate (Salt/Mix); Resoquine (Salt/Mix); Spectrum_000132; Chloroquine + Proveblue; Prestwick0_000548; Prestwick1_000548; Prestwick2_000548; Prestwick3_000548; Spectrum2_000127; Spectrum3_000341; Spectrum4_000279; Spectrum5_000707; (.+/-.)-Chloroquine; 1,4-Pentanediamine, N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-; Epitope ID:131785; MolMap_000009; SCHEMBL8933; Lopac0_000296; BSPBio_000595; BSPBio_002001; KBioGR_000778; KBioSS_000592; DivK1c_000404; CU-01000012392-2; SPBio_000174; SPBio_002516; GNF-Pf-4216; BPBio1_000655; GTPL5535; DTXSID2040446; BDBM22985; KBio1_000404; KBio2_000592; KBio2_003160; KBio2_005728; KBio3_001221; NINDS_000404; HMS2090O03; ALBB-025694; HY-17589A; s6999; SBB072644; AKOS015935106; CCG-204391; CS-W004760; DB00608; KH-0005; MCULE-3610827164; SDCCGSBI-0050284.P005; IDI1_000404; SMP2_000034; NCGC00015256-02; NCGC00015256-03; NCGC00015256-04; NCGC00015256-05; NCGC00015256-06; NCGC00015256-07; NCGC00015256-08; NCGC00015256-09; NCGC00015256-10; NCGC00015256-13; NCGC00015256-17; NCGC00015256-28; NCGC00162120-01; AK116457; NCI60_000894; SY086904; WLN: T66 BNJ EMY1&3N2&2 IG; SBI-0050284.P004; AB00053436; CS-0021871; FT-0623612; ST45028748; C07625; D02366; MLS-0466768.0001; AB00053436-05; AB00053436_06; AB00053436_07; 1, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-; Q422438; BRD-A91699651-065-01-1; BRD-A91699651-316-06-7; n(sup4)-(7-chloro-4-quinolinyl)-n(sup1),4-pentanediamine; N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine; N4-(7-chloro-4-quinolyl)-N1,N1-diethyl-pentane-1,4-diamine; Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-; N(4)-(7-chloroquinolin-4-yl)-N(1),N(1)-diethylpentane-1,4-diamine; 1,4-pentanediamine, N~4~-(7-chloro-4-quinolinyl)-N~1~,N~1~-diethyl-, phosphate (1:2); N(sup4)-(7-chloro-4-quinolinyl)-N(sup1),N(sup1)-diethyl-1,4-pentanediamine; 117399-83-4; Chloroquine; Chloroquine Sulphate; 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
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Molecular Type
Small molecule
Disease Malaria [ICD-11: 1F40] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C18H26ClN3
PubChem CID
2719
Canonical SMILES
CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
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
CAS Number
CAS 54-05-7
ChEBI ID
CHEBI:3638
TTD Drug ID
D09EGZ
DrugBank ID
DB00608
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     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
                    Molecule(s)
                    Regulation		 Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Expression SQSTM1  Molecule Info 
Pathway MAP
                    In-vitro Model NB4 CVCL_0005 Acute promyelocytic leukemia Homo sapiens
                    Experimental
                    Result(s)		 CQ exhibits a cytotoxic effect on NB4 cells and has a synergistic effect when combined with ATO, which thereby improves the curative effect of ATO on APL.
          Febrifugine      Dichroa febrifuga     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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Mice were infected intraperitoneally with parasitized erythro-cytes.
                    Experimental
                    Result(s)		 Malaria parasites in the mice given chloroquine plus alkaloids decreased on day 6 and then were not detected by a microscopic examination during observation period.
          Gambogic acid      Garcinia morella     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BECN1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Expression SQSTM1  Molecule Info 
Pathway MAP
                    In-vitro Model PANC-1 CVCL_0480 Pancreatic ductal adenocarcinoma Homo sapiens
BxPC-3 CVCL_0186 Pancreatic ductal adenocarcinoma Homo sapiens
                    In-vivo Model Xenograft tumor models were created by subcutaneously injecting 5*106 BxPC-3 cells into the right flank of the mice.
                    Experimental
                    Result(s)		 Gambogic acid induces autophagy and combines synergistically with chloroquine to suppress pancreatic cancer by increasing the accumulation of reactive oxygen species.
          Honokiol      Magnolia officinalis     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Expression SQSTM1  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Honokiol exhibits enhanced antitumor effects with chloroquine by inducing cell death and inhibiting autophagy in human non-small cell lung cancer cells.
          Quercetin      Averrhoa carambola     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Ca(2+) homeostasis disruption
Induction Lysosomal defects
                    In-vitro Model T98G CVCL_0556 Glioblastoma Homo sapiens
U-251MG CVCL_0021 Astrocytoma Homo sapiens
U-373MG ATCC CVCL_2219 Astrocytoma Homo sapiens
                    Experimental
                    Result(s)		 Quercetin and chloroquine synergistically kill glioma cells by inducing organelle stress and disrupting Ca2+ homeostasis.
Target and Pathway
Target(s) Duffy antigen chemokine receptor (ACKR1)  Molecule Info  [7]
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: 5535).
Reference 2 Chloroquine exerts antitumor effects on NB4 acute promyelocytic leukemia cells and functions synergistically with arsenic trioxide. Oncol Lett. 2018 Feb;15(2):2024-2030.
Reference 3 Combination effects of chloroquine with the febrifugine and isofebrifugine mixture against a blood-induced infection with chloroquine-resistant Plasmodium berghei NK65 in ICR mice. Phytother Res. 2003 Dec;17(10):1234-6.
Reference 4 Gambogic acid induces autophagy and combines synergistically with chloroquine to suppress pancreatic cancer by increasing the accumulation of reactive oxygen species. Cancer Cell Int. 2019 Jan 5;19:7.
Reference 5 Honokiol exhibits enhanced antitumor effects with chloroquine by inducing cell death and inhibiting autophagy in human non-small cell lung cancer cells. Oncol Rep. 2015 Sep;34(3):1289-300.
Reference 6 Quercetin and chloroquine synergistically kill glioma cells by inducing organelle stress and disrupting Ca 2+ homeostasis. Biochem Pharmacol. 2020 Aug;178:114098.
Reference 7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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