Tìm theo
Levamisole
Các tên gọi khác (2) :
  • Levamisol
  • Levamisolum
antirheumatic agents, adjuvants immunologic, antinematodal agents
Thuốc Gốc
Small Molecule
CAS: 14769-73-4
ATC: P02CE01
ĐG : Professional Co.
CTHH: C11H12N2S
PTK: 204.291
An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). Levamisole was withdrawn from the US and Canadian markets in 2000 and 2003, respectively, due to the risk of serious side effects and the availability of more effective replacement medications. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C11H12N2S
Phân tử khối
204.291
Monoisotopic mass
204.072119084
InChI
InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
InChI Key
InChIKey=HLFSDGLLUJUHTE-SNVBAGLBSA-N
IUPAC Name
(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
Traditional IUPAC Name
levamisole
SMILES
C1CN2C[C@@H](N=C2S1)C1=CC=CC=C1
Độ tan chảy
227-227.5
Độ hòa tan
210 mg/mL
logP
1.84
logS
-2.1
pKa (Strongest Basic)
6.98
PSA
15.6 Å2
Refractivity
60.08 m3·mol-1
Polarizability
22.35 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Levamisole is a synthetic imidazothiazole derivative that has been widely used in treatment of worm infestations in both humans and animals. As an anthelmintic, it probably works by targeting the nematode nicotinergic acetylcholine receptor. As an immunomodulator, it appears that Levamisole is an immunostimulant which has been shown to increase NK cells and activated T-cells in patients receiving this adjuvantly along with 5FU for Stage III colon cancer.
Cơ Chế Tác Dụng : An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). Levamisole was withdrawn from the US and Canadian markets in 2000 and 2003, respectively, due to the risk of serious side effects and the availability of more effective replacement medications. [Wikipedia] The mechanism of action of levamisole as an antiparasitic agent appears to be tied to its agnositic activity towards the L-subtype nicotinic acetylcholine receptors in nematode muscles. This agonistic action reduces the capacity of the males to control their reproductive muscles and limits their ability to copulate. The mechanism of action of Levamisole as an anticancer drug in combination with fluorouracil is unknown. The effects of levamisole on the immune system are complex. The drug appears to restore depressed immune function rather than to stimulate response to above-normal levels. Levamisole can stimulate formation of antibodies to various antigens, enhance T-cell responses by stimulating T-cell activation and proliferation, potentiate monocyte and macrophage functions including phagocytosis and chemotaxis, and increase neutrophil mobility, adherence, and chemotaxis.
Dược Động Học :
▧ Absorption :
Levamisole is rapidly absorbed (2 hours) from the gastrointestinal tract.
▧ Protein binding :
20-25%
▧ Metabolism :
Primarily hepatic (extensive) with both active and inactive metabolites.
▧ Half Life :
4.4-5.6 hours (biphasic)
Độc Tính : LD50 = 40 mg/kg (Pigs, subcutaneous); LD50 = 180 mg/kg (rat, oral)
Chỉ Định : For adjuvant treatment in combination with fluorouracil after surgical resection in patients with Dukes' stage C colon cancer. Also used to treat malignant melanoma and head/neck cancer. Levamisole was originally used as an antihelminthic to treat worm infestations in both humans and animals.
Tương Tác Thuốc :
  • Acenocoumarol Levamisole may increase the anticoagulant effect of acenocoumarol.
  • Anisindione Levamisole may increase the anticoagulant effect of anisindione.
  • Dicoumarol Levamisole may increase the anticoagulant effect of dicumarol.
  • Warfarin Levamisole may increase the anticoagulant effect of warfarin.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Janssen
    Sản phẩm biệt dược : Ergamisol
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Ketrax
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00848
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=26879
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46509052
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07070
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D08114
ChemSpider
http://www.chemspider.com/Chemical-Structure.25037.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50241179
PharmGKB
http://www.pharmgkb.org/drug/PA450205
Wikipedia
http://en.wikipedia.org/wiki/Levamisole
RxList
http://www.rxlist.com/cgi/generic3/levamisole.htm
Drugs.com
http://www.drugs.com/mtm/levamisole.html
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