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

• ChemBase编号: 974
• 分子式: C23H30ClN3O
• 平均质量: 399.9568
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: {4-[(6-chloro-2-methoxyacridin-9-yl)amino]pentyl}diethylamine
• IUPAC传统名: quinacrine
• 商标名: Acrichine; Acrinamine; Acriquine; Akrichin; Antimalarina; Atabrine; Atebrin; Atebrine; Erion; Erion Hydrochloride; Haffkinine; Italchine; Mepacrine; Quinactine
• 别名: Quinacrine Dihydrochloride; Quinacrine

登记号

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

理论计算性质

JChem

• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -3.9949434E-4
• LogD (pH = 7.4): 1.3863823
• Log P: 5.151537
• 摩尔折射率: 118.9644 cm^3
• 极化性: 48.14002 Å^3
• 极化表面积: 37.39 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 6.13
• LOG S: -5.22
• 溶解度: 2.39e-03 g/l

分子性质

理化性质

• 溶解度: Slight
• 疏水性(logP): 5.5

详细说明

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• Description: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years.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

参考文献

• 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