Human Metabolome Database Version 3.5

Showing metabocard for Quinacrine (HMDB15235)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:15 -0700
HMDB ID HMDB15235
Secondary Accession Numbers None
Metabolite Identification
Common Name Quinacrine
Description An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years.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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Quinacrine Dihydrochloride
Chemical Formula C23H30ClN3O
Average Molecular Weight 399.957
Monoisotopic Molecular Weight 399.207740304
IUPAC Name {4-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl}diethylamine
Traditional IUPAC Name quinacrine
CAS Registry Number 83-89-6
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 Key GPKJTRJOBQGKQK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class Benzoquinolines
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 Parent Acridines
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 248 - 250 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.39e-03 g/L Not Available
LogP 5.5 Not Available
Predicted Properties
Property Value Source
LogP 6.13 ALOGPS
LogP 5.15 ChemAxon
LogS -5.22 ALOGPS
pKa (strongest basic) 10.33 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.39 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 118.96 ChemAxon
Polarizability 46.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01103
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01103
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01103 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 232 Link_out
KEGG Compound ID C07339 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Quinacrine Link_out
NuGOwiki Link HMDB15235 Link_out
Metagene Link HMDB15235 Link_out
METLIN ID Not Available
PubChem Compound 237 Link_out
PDB ID Not Available
ChEBI ID 8711 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histamine N-methyltransferase
Reactions: Not Available
Gene Name: HNMT
Uniprot ID: P50135 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Multidrug resistance protein 1
Reactions: Not Available
Gene Name: ABCB1
Uniprot ID: P08183 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 2
Reactions: Not Available
Gene Name: SLC22A2
Uniprot ID: O15244 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA