ChemFOnt: Showing chemical card for Chloroquine (CFc000009094)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:07 UTC

Chemfont ID

CFc000009094

Molecule Identification

Common Name

Chloroquine

Definition

Chloroquine is only found in individuals that have used or taken this drug. It is a prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem]The mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell.During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals.Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products.

Structure

MOL SDF PDB SMILES InChI

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 Molecular Weight

319.872

Monoisotopic Molecular Weight

319.181525554

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

54-05-7

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

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014746)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
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