Quinacrine Dihydrochloride Dihydrate

Names

[ CAS No. ]:
83-89-6

[ Name ]:
Quinacrine Dihydrochloride Dihydrate

[Synonym ]:
Quinacrine Dihydrochloride Dihydrate
2-methoxy-6-chloro-9-(1-methyl-4-diethylaminobutylamino)-acridine
2-methoxy-6-(trifluoromethyl)nicotinic acid
2-METHOXY-6-(TRIFLUOROMETHYL)-3-PYRIDINECARBOXYLIC ACID

Biological Activity

[Description]:

Quinacrine (Acriquine) is an antimalarial and anti-cancer agent. Quinacrine also inhibits human aldehyde oxidase (IC50: 3.3 μM). Quinacrine has affinity for nucleic acids, and stains DNA and RNA in fixed cells (Ex/Em: 436/525 nm)[1][2][3][4][7].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Cancer

Research Areas >> Infection

Research Areas >> Neurological Disease

[In Vitro]

Quinacrine 抑制人和兔醛氧化酶，IC50 分别为 3.3 μM 和 10 μM[2]。 Quinacrine 阻断电压依赖性钠通道 (IC50: 3.3 μM)[3]。 Quinacrine (100 μM) 也是一种 PLA2 抑制剂[4]。 Quinacrine (0-20 μM, 24 h) 抑制 SGC-7901 细胞的生长，并诱导细胞凋亡[7]。 Cell Viability AssayQuinacrine 抑制人和兔醛氧化酶，IC50 分别为 3.3 μM 和 10 μM[2]。 Cell Line: SGC-7901 cell Concentration: 0, 5, 10, 15, 20 μM Incubation Time: 24 h Result: Inhibited cell growth with an IC50 value of 16.18 μM.

[In Vivo]

Quinacrine (3-30 mg/kg，i.p.，每日一次，连续三天) 对甘油诱导的大鼠急性肾损伤具有保护作用[5]。 Quinacrine (2.5-10 mg/kg，i.p.，每天一次，连续八周) 对环孢菌素引起的大鼠肾毒性具有保护作用[6]。 Animal Model: Acute kidney injury rat model[5] Dosage: 3-30 mg/kg Administration: i.p. Result: Attenuated glycerol induced structural and functional changes in kidney.

[References]

[1]. Vogtherr M, et al. Antimalarial drug quinacrine binds to C-terminal helix of cellular prion protein. J Med Chem. 2003 Aug 14;46(17):3563-4.

[2]. Pryde DC, et al. Aldehyde oxidase: an enzyme of emerging importance in drug discovery. J Med Chem. 2010 Dec 23;53(24):8441-60.

[3]. McNeal ET, et al. [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs. J Med Chem. 1985 Mar;28(3):381-8.

[4]. Caro AA,et al. Role of phospholipase A2 activation and calcium in CYP2E1-dependent toxicity in HepG2 cells. J Biol Chem. 2003 Sep 5;278(36):33866-77.

[5]. Al Asmari AK, et al. Protective effect of quinacrine against glycerol-induced acute kidney injury in rats. BMC Nephrol. 2017 Jan 28;18(1):41.

[6]. al Khader A, et al. Quinacrine attenuates cyclosporine-induced nephrotoxicity in rats. Transplantation. 1996 Aug 27;62(4):427-35.

[7]. Wu X, et al. Quinacrine Inhibits Cell Growth and Induces Apoptosis in Human Gastric Cancer Cell Line SGC-7901. Curr Ther Res Clin Exp. 2012 Feb;73(1-2):52-64.

Chemical & Physical Properties

[ Density]:
1.156 g/cm3

[ Boiling Point ]:
557.1ºC at 760 mmHg

[ Melting Point ]:
247-250ºC

[ Molecular Formula ]:
C₂₃H₃₀ClN₃O

[ Molecular Weight ]:
399.96

[ Flash Point ]:
290.7ºC

[ Exact Mass ]:
399.20800

[ PSA ]:
37.39000

[ LogP ]:
6.04540

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR7700000

CHEMICAL NAME :: Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2- methoxy-

CAS REGISTRY NUMBER :: 83-89-6

LAST UPDATED :: 199710

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C23-H30-Cl-N3-O

MOLECULAR WEIGHT :: 400.01

WISWESSER LINE NOTATION :: T C666 BNJ EG IMY1&3N2&2 LO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 239 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 8 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 714 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - coma Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 13600 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: Specific locus test

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 1 umol/L

REFERENCE :: CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 8,113,1974 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R36/37/38