ChemFOnt: Showing chemical card for Hydroxychloroquine (CFc000009811)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:04 UTC

Chemfont ID

CFc000009811

Molecule Identification

Common Name

Hydroxychloroquine

Definition

Hydroxychloroquine is only found in individuals that have used or taken this drug. It is a chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Hydroxychloroquine	ChEBI
2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol	ChEBI
2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol	ChEBI
7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline	ChEBI
7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline	ChEBI
7-Chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline	ChEBI
7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline	ChEBI
Hidroxicloroquina	ChEBI
Hydroxychloroquinum	ChEBI
NSC4375	ChEBI
Oxichlorochine	ChEBI
Oxichloroquine	ChEBI
Polirreumin	ChEBI
7-Chloro-4-(4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino)quinoline	Generator
7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinoline	Generator
7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline	Generator
7-Chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline	Generator
HCQ	HMDB
Oxychlorochin	HMDB
Hydroxychloroquine sulfate (1:1) salt	HMDB
Oxychloroquine	HMDB
Hydroxychlorochin	HMDB
Hydroxychloroquine sulfate	HMDB
Plaquenil	HMDB

Chemical Formula

C₁₈H₂₆ClN₃O

Average Molecular Weight

335.872

Monoisotopic Molecular Weight

335.176440176

IUPAC Name

2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol

Traditional Name

hydroxychloroquine

CAS Registry Number

118-42-3

SMILES

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

InChI Identifier

InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)

InChI Key

XXSMGPRMXLTPCZ-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

Chloroquinoline
4-aminoquinoline
Haloquinoline
Aminopyridine
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Secondary amine
Azacycle
Alkanolamine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:5801 )
organochlorine compound (CHEBI:5801 )
secondary amino compound (CHEBI:5801 )
primary alcohol (CHEBI:5801 )
aminoquinoline (CHEBI:5801 )

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

Cytoplasm (HMDB: HMDB0015549)
Membrane (HMDB: HMDB0015549)

Source

Exogenous

Exogenous (HMDB: HMDB0015549)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antirheumatic drug (HMDB: HMDB0015549)
Dermatologic drug (HMDB: HMDB0015549)

Antimicrobial agent

Antimalarial (HMDB: HMDB0015549)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.87	ALOGPS
logP	2.89	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	38.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon