Chloroquine

Details

• Internal ID: bbd226f0-c398-4b79-9495-950c09f392bc
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Aminoquinolines and derivatives > 4-aminoquinolines
• IUPAC Name: 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• SMILES (Canonical): CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl
• SMILES (Isomeric): 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)
• InChI Key: WHTVZRBIWZFKQO-UHFFFAOYSA-N
• Popularity: 32,567 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆ClN₃
• Molecular Weight: 319.90 g/mol
• Exact Mass: 319.1815255 g/mol
• Topological Polar Surface Area (TPSA): 28.20 Ų
• XlogP: 4.60

Synonyms

• 54-05-7
• Aralen
• Chlorochin
• Chloraquine
• Artrichin
• Chloroquina
• Chloroquinium
• Capquin
• Reumachlor
• Chemochin
• Chlorquin
• Clorochina
• Malaquin
• Bemaco
• Arthrochin
• Bemasulph
• Chingamin
• Cidanchin
• Cocartrit
• Dichinalex
• Gontochin
• Pfizerquine
• Quinachlor
• Quinercyl
• Quinoscan
• Tresochin
• Benaquin
• Bipiquin
• Elestol
• Heliopar
• Iroquine
• Klorokin
• Lapaquin
• Malaren
• Mesylith
• Neochin
• Quinilon
• Roquine
• Sanoquin
• Silbesan
• Siragan
• Solprina
• Sopaquin
• Trochin
• Amokin
• Imagon
• Nivaquine B
• Khingamin
• Malarex
• Chloroquinum
• Cloroquina
• Ronaquine
• Bemaphate
• Nivaquine
• Resoquine
• Chlorochine
• Chlorochinum
• Quinagamine
• N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine
• Avlochlor
• Nivachine
• Quinagamin
• Quingamine
• Resochen
• Resoquina
• Reumaquin
• WIN 244
• ST 21 (pharmaceutical)
• Chloroquine (VAN)
• Clorochina [DCIT]
• Arechine
• Arequin
• RP 3377
• 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-
• Chloroquinum [INN-Latin]
• Cloroquina [INN-Spanish]
• W 7618
• (+-)-Chloroquine
• 3377 RP opalate
• Chloroquin
• CCRIS 3439
• CHEBI:3638
• Chloroin
• Rivoquine
• Arolen
• HSDB 3029
• ST 21
• 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline
• N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
• EINECS 200-191-2
• UNII-886U3H6UFF
• Miniquine
• Tanakene
• NSC 187208
• NSC-187208
• ( -)-Chloroquine
• BRN 0482809
• Chloroquine [USAN:INN:BAN]
• 886U3H6UFF
• Aralen HCl
• {4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine
• Gontochin phosphate
• CHEMBL76
• Chloroquine (USP/INN)
• Malaquin (*Diphosphate*)
• 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• SN 6718
• C18H26ClN3
• Chloroquine [USP:INN:BAN]
• Ipsen 225
• N(sup 4)-(7-Chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-1,4-pentanediamine
• CQ
• DTXSID2040446
• 7-Chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline
• Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-
• 1,4-Pentanediamine, N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-
• MFCD00024009
• NSC187208
• RP-3377
• Ro 01-6014/N2
• N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine
• 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-
• CHLOROQUINE (MART.)
• CHLOROQUINE [MART.]
• CU-01000012392-2
• C18-H26-Cl-N3
• Chloroquine, D-
• CHLOROQUINE (USP IMPURITY)
• CHLOROQUINE [USP IMPURITY]
• CHLOROQUINE (USP MONOGRAPH)
• CHLOROQUINE [USP MONOGRAPH]
• Quinoline, 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]-
• N(4)-(7-chloroquinolin-4-yl)-N(1),N(1)-diethylpentane-1,4-diamine
• 1,4-PENTANEDIAMINE, N(SUP 4)-(7-CHLORO-4-QUINOLINYL)-N(SUP 1),N (SUP 1)-DIETHYL-
• NSC14050
• Cloroquine
• chloroquin-
• Chloroquine Bis-Phosphoric Acid
• 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (+)-
• ( )-Chloroquine
• Chloroquine, 17
• Dawaquin (TN)
• Resochin (TN)
• 4,7-Dichloroquine
• Arechin (Salt/Mix)
• Delagil (Salt/Mix)
• Tanakan (Salt/Mix)
• Bemaphate (Salt/Mix)
• Resoquine (Salt/Mix)
• Spectrum_000132
• Chloroquine + Proveblue
• Chloroquine FNA (TN)
• CHLOROQUINE [MI]
• Prestwick0_000548
• Prestwick1_000548
• Prestwick2_000548
• Prestwick3_000548
• Spectrum2_000127
• Spectrum3_000341
• Spectrum4_000279
• Spectrum5_000707
• CHLOROQUINE [INN]
• (.+/-.)-Chloroquine
• CHLOROQUINE [HSDB]
• D09EGZ
• Epitope ID:131785
• MolMap_000009
• CHLOROQUINE [VANDF]
• SCHEMBL8933
• Lopac0_000296
• BSPBio_000595
• BSPBio_002001
• CHLOROQUINE [WHO-DD]
• KBioGR_000778
• KBioSS_000592
• DivK1c_000404
• SPBio_000174
• SPBio_002516
• (+)-N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
• Chloroquine [USAN:BAN:INN]
• GNF-Pf-4216
• BPBio1_000655
• GTPL5535
• DTXCID0020446
• BDBM22985
• KBio1_000404
• KBio2_000592
• KBio2_003160
• KBio2_005728
• KBio3_001221
• P01BA01
• NINDS_000404
• HMS2090O03
• HY-17589A
• s6999
• AKOS015935106
• CCG-204391
• CS-W004760
• DB00608
• KH-0005
• SB73098
• 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
• NCI60_000894
• SY086904
• WLN: T66 BNJ EMY1&3N2&2 IG
• N(C(C)CCCN(CC)CC)c1ccnc2cc(Cl)ccc12
• SBI-0050284.P004
• LS-141726
• AB00053436
• C3730
• CS-0021871
• FT-0623612
• C07625
• D02366
• EN300-120683
• 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
• 7-chloro-4-(4-diethylamino-1-methylbutylamino)quinoline
• (7-Chloro-4-(4-diethylamino-1-methylbutylamino)-quinoline
• 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)-
• 7-CHLORO-N-[5-(DIETHYLAMINO)PENTAN-2-YL]QUINOLIN-4-AMINE
• (+-)-N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
• 1,4-Pentanediamine, N(4)-(7-chloro-4-quinolinyl)-N(1)-,N(1)-diethyl-
• 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (+-)-
• N(sup4)-(7-chloro-4-quinolinyl)-N(sup1),N(sup1)-diethyl-1,4-pentanediamine
• 117399-83-4
• 56598-66-4
• Chloroquine; Chloroquine Sulphate; 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL240	Q12809	HERG	2500 nM; 2500 nM; 2500 nM	IC50; IC50; IC50	PMID: 11012023; PMID: 14640511; via CMAUP
CHEMBL4869	P04156	Prion protein	4000 nM	EC50	PMID: 22037378
CHEMBL3959	P16083	Quinone reductase 2	1500 nM	IC50	via CMAUP
CHEMBL287	Q99720	Sigma opioid receptor	79.43 nM	Ki	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.19%	89.76%
CHEMBL3401	O75469	Pregnane X receptor	97.01%	94.73%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.32%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.82%	91.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	91.57%	100.00%
CHEMBL2916	O14746	Telomerase reverse transcriptase	90.86%	90.00%
CHEMBL202	P00374	Dihydrofolate reductase	90.57%	89.92%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	90.26%	97.23%
CHEMBL226	P30542	Adenosine A1 receptor	89.85%	95.93%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	89.21%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.99%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.27%	90.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.50%	89.44%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.35%	93.81%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.17%	96.90%
CHEMBL255	P29275	Adenosine A2b receptor	85.96%	98.59%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.95%	92.29%
CHEMBL220	P22303	Acetylcholinesterase	85.87%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.28%	90.71%
CHEMBL3524	P56524	Histone deacetylase 4	85.11%	92.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.84%	86.33%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	83.03%	99.00%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.29%	92.50%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	81.10%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.22%	94.00%

Plants that contains it

• Alkanna orientalis
• Cinchona calisaya
• Montanoa tomentosa

Cross-Links

• PubChem: 2719
• NPASS: NPC476464
• ChEMBL: CHEMBL76
• LOTUS: LTS0192132
• wikiData: Q105305166