NP-MRD: Showing NP-Card for chloroquine (NP0274960)

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Record Information

Version

2.0

Created at

2022-09-08 22:32:10 UTC

Updated at

2022-09-08 22:32:10 UTC

NP-MRD ID

NP0274960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chloroquine

Description

Chloroquine, also known as chlorochin or nivaquine b, belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. Chloroquine is a very strong basic compound (based on its pKa). Chloroquine is a potentially toxic compound. chloroquine is found in Alkanna orientalis and Cinchona calisaya. chloroquine was first documented in 2000 (PMID: 11198399). An aminoquinoline that is quinoline which is substituted at position 4 by a amino group at at position 7 by chlorine (PMID: 17594118) (PMID: 18052874) (PMID: 19426658) (PMID: 23288916).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
   -5.1669   -0.6028   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9147   -1.4151   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8525   -1.1152   -0.5000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775   -1.4641    0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740   -0.7237    1.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0457   -0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0386    0.4151    0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3355    1.6708   -0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    2.1216    0.5270 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2820    2.4365    1.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    1.1144    0.6155 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6739    0.8237   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6458    1.6562   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    1.4002   -2.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3912    0.3757   -2.5012 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4309   -0.4457   -1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3191   -1.4815   -1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4118   -2.3498   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5522   -3.6639   -0.2482 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -2.1136    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6224   -1.0782    0.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521   -0.2261   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468    0.4574   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8708   -1.0391   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7061   -0.5516   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341   -2.4850   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6461   -1.3633   -2.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3189   -2.5503    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731   -1.5339    1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9612   -1.2670    1.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800   -0.7558    2.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1999    0.2961    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811   -0.2084   -1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492    0.9034   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667   -0.3483    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501    0.7301    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398    1.4462   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    2.5106   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2245    3.0545    0.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228    2.4711    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259    1.6717    2.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936    3.4065    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005    0.5669    1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708    2.5003   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4861    2.0674   -3.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9799   -1.6124   -2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -2.7855    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717   -0.9617    1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 22  2  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 16 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 21 48  1  0
 20 47  1  0
 17 46  1  0
 14 45  1  0
 13 44  1  0
M  END

608
  Mrv0541 02231214482D          

 22 23  0  0  1  0            999 V2000
    8.1347    3.3056    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    3.2857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  0  0  0  0
  4 17  2  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  2  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0274960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C18H26ClN3

> <MOLECULAR_WEIGHT>
319.872

> <EXACT_MASS>
319.181525554

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.28790341691832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
3.933881141333334

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.324447273782475

> <JCHEM_POLAR_SURFACE_AREA>
28.16

> <JCHEM_REFRACTIVITY>
96.42300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 608                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      15.185   6.170   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       5.747  -3.877   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.748   1.513   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.748   6.133   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.415  -0.797   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   0.743   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -3.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -5.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.107   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   3.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082   3.823   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -6.187   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -3.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   3.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   5.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.459   3.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   5.363   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.459   6.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854   3.791   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854   5.395   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2    8   10   11                                                  
CONECT    3    7   12                                                       
CONECT    4   17   19                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    3    5    9                                                  
CONECT    8    2    6                                                       
CONECT    9    7                                                            
CONECT   10    2   14                                                       
CONECT   11    2   15                                                       
CONECT   12    3   13   16                                                  
CONECT   13   12   17   18                                                  
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12   19                                                       
CONECT   17    4   13   20                                                  
CONECT   18   13   21                                                       
CONECT   19    4   16                                                       
CONECT   20   17   22                                                       
CONECT   21   18   22                                                       
CONECT   22    1   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Aralen	ChEBI
Artrichin	ChEBI
Bemaphate	ChEBI
Capquin	ChEBI
Chlorochin	ChEBI
Chloroquinum	ChEBI
Cloroquina	ChEBI
N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine	ChEBI
Nivaquine b	ChEBI
Resoquine	ChEBI
Reumachlor	ChEBI
Sanoquin	ChEBI
Bemaphic acid	Generator
Chloraquine	HMDB
Chlorochine	HMDB
Chloroquina	HMDB
Chloroquinium	HMDB
Chlorquin	HMDB
Clorochina	HMDB
Chingamin	HMDB
Arechine	HMDB
Khingamin	HMDB
Sulphate, chloroquine	HMDB
Arequin	HMDB
Chloroquine sulfate	HMDB
Chloroquine sulphate	HMDB
Nivaquine	HMDB
Sulfate, chloroquine	HMDB

Chemical Formula

C₁₈H₂₆ClN₃

Average Mass

319.8720 Da

Monoisotopic Mass

319.18153 Da

IUPAC Name

7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine

Traditional Name

7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine

CAS Registry Number

Not Available

SMILES

CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alkanna orientalis	LOTUS Database	35616633
Cinchona calisaya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminopyridine
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Secondary amine
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:3638 )
organochlorine compound (CHEBI:3638 )
secondary amino compound (CHEBI:3638 )
aminoquinoline (CHEBI:3638 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.28	ALOGPS
logP	3.93	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	96.42 m³·mol⁻¹	ChemAxon
Polarizability	37.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014746

DrugBank ID

DB00608

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2618

KEGG Compound ID

C07625

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chloroquine

METLIN ID

Not Available

PubChem Compound

2719

PDB ID

Not Available

ChEBI ID

3638

Good Scents ID

Not Available

References

General References

Nandi J, Sharma SN: Efficacy of chloroquine in febrile Plasmodium falciparum infected children in Mewat region of Haryana. J Commun Dis. 2000 Jun;32(2):137-43. [PubMed:11198399 ]
Bortoli R, Santiago M: Chloroquine ototoxicity. Clin Rheumatol. 2007 Nov;26(11):1809-10. doi: 10.1007/s10067-007-0662-6. Epub 2007 Jun 27. [PubMed:17594118 ]
Cooper RG, Magwere T: Chloroquine has not disappeared. Afr Health Sci. 2007 Sep;7(3):185-6. doi: 10.5555/afhs.2007.7.3.185. [PubMed:18052874 ]
Valecha N, Joshi H, Mallick PK, Sharma SK, Kumar A, Tyagi PK, Shahi B, Das MK, Nagpal BN, Dash AP: Low efficacy of chloroquine: time to switchover to artemisinin-based combination therapy for falciparum malaria in India. Acta Trop. 2009 Jul;111(1):21-8. doi: 10.1016/j.actatropica.2009.01.013. Epub 2009 Feb 7. [PubMed:19426658 ]
Kimura T, Takabatake Y, Takahashi A, Isaka Y: Chloroquine in cancer therapy: a double-edged sword of autophagy. Cancer Res. 2013 Jan 1;73(1):3-7. doi: 10.1158/0008-5472.CAN-12-2464. [PubMed:23288916 ]
LOTUS database [Link]

Showing NP-Card for chloroquine (NP0274960)

MOL for NP0274960 (chloroquine)

3D MOL for NP0274960 (chloroquine)

3D SDF for NP0274960 (chloroquine)

3D-SDF for NP0274960 (chloroquine)

PDB for NP0274960 (chloroquine)

3D PDB for NP0274960 (chloroquine)

SMILES for NP0274960 (chloroquine)

INCHI for NP0274960 (chloroquine)

Structure for NP0274960 (chloroquine)

3D Structure for NP0274960 (chloroquine)