Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:15 UTC
HMDB IDHMDB15235
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuinacrine
DescriptionAn acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2. [PubChem]
Structure
Thumb
Synonyms
  1. Quinacrine Dihydrochloride
Chemical FormulaC23H30ClN3O
Average Molecular Weight399.957
Monoisotopic Molecular Weight399.207740304
IUPAC Name{4-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl}diethylamine
Traditional IUPAC Namequinacrine
CAS Registry Number83-89-6
SMILES
CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2
InChI Identifier
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
InChI KeyGPKJTRJOBQGKQK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassBenzoquinolines
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • acridines(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Aminopyridine
  • Aminoquinoline
  • Anisole
  • Aryl Chloride
  • Chlorobenzene
  • Hydroxyquinoline
  • Organochloride
  • Polyamine
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentAcridines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Anticestodal Agents
  • Antihelmintics
  • Antimalarials
  • Antinematodal Agents
  • Antineoplastic Agents
  • Antiprotozoals
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point248 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.39e-03 g/LNot Available
LogP5.5Not Available
Predicted Properties
PropertyValueSource
water solubility0.0024 g/LALOGPS
logP6.13ALOGPS
logP5.15ChemAxon
logS-5.2ALOGPS
pKa (strongest basic)10.33ChemAxon
physiological charge2ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.39ChemAxon
rotatable bond count9ChemAxon
refractivity118.96ChemAxon
polarizability46.32ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01103
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01103
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01103
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID232
KEGG Compound IDC07339
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinacrine
NuGOwiki LinkHMDB15235
Metagene LinkHMDB15235
METLIN IDNot Available
PubChem Compound237
PDB IDNot Available
ChEBI ID8711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. Pubmed: 1839351
  2. Zipper J, Cole LP, Goldsmith A, Wheeler R, Rivera M: Quinacrine hydrochloride pellets: preliminary data on a nonsurgical method of female sterilization. Int J Gynaecol Obstet. 1980;18(4):275-9. Pubmed: 6109672
  3. Peterson HB, Lubell I, DeStefano F, Ory HW: The safety and efficacy of tubal sterilization: an international overview. Int J Gynaecol Obstet. 1983 Apr;21(2):139-44. Pubmed: 6136433
  4. Toubi E, Kessel A, Rosner I, Rozenbaum M, Paran D, Shoenfeld Y: The reduction of serum B-lymphocyte activating factor levels following quinacrine add-on therapy in systemic lupus erythematosus. Scand J Immunol. 2006 Apr;63(4):299-303. Pubmed: 16623930
  5. Canete R, Escobedo AA, Gonzalez ME, Almirall P: Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children. World J Gastroenterol. 2006 Oct 21;12(39):6366-70. Pubmed: 17072963

Enzymes

Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
HNMT
Uniprot ID:
P50135
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP3A5
Uniprot ID:
P20815

Transporters

Gene Name:
ABCB1
Uniprot ID:
P08183
Gene Name:
SLC22A2
Uniprot ID:
O15244