Tìm theo
Chloroquine
Các tên gọi khác (18 ) :
  • Aralen
  • Artrichin
  • Bemaphate
  • Capquin
  • Chloraquine
  • Chlorochin
  • Chlorochine
  • Chloroquina
  • Chloroquine
  • Chloroquinium
  • Chloroquinum
  • Cloroquina
  • N(4)-(7-chloro-4-Quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine
  • Nivaquine b
  • Resochin
  • Resoquine
  • Reumachlor
  • Sanoquin
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 54-05-7
ATC: P01BA01, P01BA02
ĐG : A-S Medication Solutions LLC , http://orders.a-smeds.com
CTHH: C18H26ClN3
PTK: 319.872
The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C18H26ClN3
Phân tử khối
319.872
Monoisotopic mass
319.181525554
InChI
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)
InChI Key
InChIKey=WHTVZRBIWZFKQO-UHFFFAOYSA-N
IUPAC Name
{4-[(7-chloroquinolin-4-yl)amino]pentyl}diethylamine
Traditional IUPAC Name
chloroquine
SMILES
CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
Độ hòa tan
10.6 mg/L
logP
4.63
logS
-4.3
pKa (Strongest Basic)
10.32
PSA
28.16 Å2
Refractivity
96.42 m3·mol-1
Polarizability
37.29 Å3
Rotatable Bond Count
8
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
2
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
10.1
Dược Lực Học : Chloroquine is the prototype anti malarial drug, most widely used to treat all types of malaria except for disease caused by chloroquine resistant Plasmodium falciparum. It is highly effective against erythrocytic forms of Plasmodium vivax, Plasmodium ovale and Plasmodium malariae, sensitive strains of Plasmodium falciparum and gametocytes of Plasmodium vivax. Being alkaline, the drug reaches high concentration within the food vacuoles of the parasite and raises its pH. It is found to induce rapid clumping of the pigment. Chloroquine inhibits the parasitic enzyme heme polymerase that converts the toxic heme into non-toxic hemazoin, thereby resulting in the accumulation of toxic heme within the parasite. It may also interfere with the biosynthesis of nucleic acids.
Cơ Chế Tác Dụng : The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem] The mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell. During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals. Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products.
Dược Động Học :
▧ Absorption :
Completely absorbed from gastrointestinal tract
▧ Protein binding :
~55% of the drug in the plasma is bound to nondiffusible plasma constituents
▧ Metabolism :
Hepatic (partially)
▧ Route of Elimination :
Excretion of chloroquine is quite slow, but is increased by acidification of the urine.
▧ Half Life :
1-2 months
Chỉ Định : For the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum, Second-line agent in treatment of Rheumatoid Arthritis
Tương Tác Thuốc :
  • Aluminium The antiacid decreases the absorption of chloroquine
  • Artemether Chloroquine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
  • Atomoxetine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
  • Attapulgite The antiacid decreases the absorption of chloroquine
  • Calcium The antiacid decreases the absorption of chloroquine
  • Cyclosporine Chloroquine may increase the therapeutic and adverse effects of cyclosporine.
  • Dihydroxyaluminium The antiacid decreases the absorption of chloroquine
  • Kaolin The antiacid decreases the absorption of chloroquine
  • Lumefantrine Chloroquine may increase the adverse effects of lumefantrine. Combination therapy is contraindicated unless there are no other treatment options.
  • Magnesium The antiacid decreases the absorption of chloroquine
  • Magnesium oxide The antiacid decreases the absorption of chloroquine
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Praziquantel Markedly lower praziquantel levels
  • Tamoxifen Chloroquine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tamsulosin Chloroquine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Chloroquine is initiated, discontinued, or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Chloroquine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Chloroquine if Telithromycin is initiated, discontinued or dose changed.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Chloroquine. Consider alternate therapy or monitor for therapeutic/adverse effects of Chloroquine if Terbinafine is initiated, discontinued or dose changed.
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Tramadol Chloroquine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of chloroquine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of chloroquine if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Sanofi
    Sản phẩm biệt dược : Aralen
  • Công ty :
    Sản phẩm biệt dược : Artrichin
  • Công ty :
    Sản phẩm biệt dược : Bemaphate
  • Công ty :
    Sản phẩm biệt dược : Capquin
  • Công ty : Actavis
    Sản phẩm biệt dược : Malarex
  • Công ty : Sanofi
    Sản phẩm biệt dược : Nivaquine B
  • Công ty :
    Sản phẩm biệt dược : Resoquine
  • Công ty :
    Sản phẩm biệt dược : Reumachlor
  • Công ty :
    Sản phẩm biệt dược : Sanoquin
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00608
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2719
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506925
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07625
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02366
ChemSpider
http://www.chemspider.com/Chemical-Structure.2618.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=22985
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0024-0084-01
PharmGKB
http://www.pharmgkb.org/drug/PA448948
Wikipedia
http://en.wikipedia.org/wiki/Chloroquine
RxList
http://www.rxlist.com/cgi/generic2/hquine2.htm
Drugs.com
http://www.drugs.com/cdi/chloroquine.html
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