{4-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl}diethylamine

• ChemBase ID: 974
• Molecular Formular: C23H30ClN3O
• Molecular Mass: 399.9568
• Monoisotopic Mass: 399.20774028
• SMILES: Clc1cc2nc3c(c(NC(CCCN(CC)CC)C)c2cc1)cc(OC)cc3
• Canonical SMILES: CCN(CCCC(Nc1c2cc(OC)ccc2nc2c1ccc(c2)Cl)C)CC
• InChI: 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)
• InChIKey: GPKJTRJOBQGKQK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl}diethylamine
• IUPAC Traditional name: quinacrine
• Brand Name: Acrichine; Acrinamine; Acriquine; Akrichin; Antimalarina; Atabrine; Atebrin; Atebrine; Erion; Erion Hydrochloride; Haffkinine; Italchine; Mepacrine; Quinactine
• Synonyms: Quinacrine Dihydrochloride; Quinacrine

Database IDs

• CAS Number: 83-89-6
• PubChem SID: 46507828; 160964437
• PubChem CID: 237

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -3.9949434E-4
• LogD (pH = 7.4): 1.3863823
• Log P: 5.151537
• Molar Refractivity: 118.9644 cm^3
• Polarizability: 48.14002 Å^3
• Polar Surface Area: 37.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.13
• LOG S: -5.22
• Solubility (Water): 2.39e-03 g/l

PROPERTIES

Physical Property

• Solubility: Slight
• Hydrophobicity(logP): 5.5

DETAILS

DrugBank - DB01103

• Drug Groups: approved
• Description: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years.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]
• Indication: For the treatment of giardiasis and cutaneous leishmaniasis and the management of malignant effusions.
• Pharmacology: Quinacrine has been used as an antimalarial drug and as an antibiotic. It is used to treat giardiasis, a protozoal infection of the intestinal tract, and certain types of lupus erythematosus, an inflammatory disease that affects the joints, tendons, and other connective tissues and organs. Quinacrine may be injected into the space surrounding the lungs to prevent reoccurrence of pneumothorax. The exact way in which quinacrine works is unknown. It appears to interfere with the parasite's metabolism.
• Toxicity: Oral, rat: LD₅₀ = 900 mg/kg; Oral, mouse: LD₅₀ = 1000 mg/kg. Symptoms of overdose include seizures, hypotension, cardiac arrhythmias, and cardiovascular collapse.
• Affected Organisms: Parasitic protozoa and helminths
• Absorption: Absorbed rapidly from the gastrointestinal tract following oral administration.
• Half Life: 5 to 14 days
• Protein Binding: 80-90%
• References: 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] ; 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] ; 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] ; Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. [Pubmed] ; 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]
• External Links: Wikipedia

REFERENCES

• 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
• 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
• 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
• Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. Pubmed
• 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