Tìm theo
Atovaquone
Các tên gọi khác (4 ) :
  • 2-(trans-4-(P-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
  • Acuvel
  • Mepron
  • Wellvone
Thuốc Gốc
Small Molecule
CAS: 95233-18-4
ATC: P01AX06
ĐG : Cardinal Health , http://www.cardinal.com
CTHH: C22H19ClO3
PTK: 366.837
A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
366.837
Monoisotopic mass
366.102272181
InChI
InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-
InChI Key
InChIKey=KUCQYCKVKVOKAY-CTYIDZIISA-N
IUPAC Name
2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC Name
atovaquone
SMILES
OC1=C([[email protected]]2CC[[email protected]@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O
Độ hòa tan
Practically insoluble
logP
5.8
logS
-5.7
pKa (strongest acidic)
8.23
pKa (Strongest Basic)
-4.1
PSA
54.37 Å2
Refractivity
103.11 m3·mol-1
Polarizability
39.55 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Atovaquone is a highly lipophilic drug that closely resembles the structure ubiquinone. Its inhibitory effect being comparable to ubiquinone, in sensitive parasites atovaquone can act by selectively affecting mitochondrial electron transport and parallel processes such as ATP and pyrimidine biosynthesis. For illustration, cytochrome bc1 complex (complex III) seems to serve as a highly discriminating molecular target for atovaquone in Plasmodia atovaquone has the advantage of not causing myelosuppression, which is an important issue in patients who have undergone bone marrow transplantation.
Cơ Chế Tác Dụng : A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. [PubChem] Atovaquone is a hydroxy- 1, 4- naphthoquinone, an analog of ubiquinone, with antipneumocystis activity. The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.
Dược Động Học :
▧ Absorption :
The bioavailability of atovaquone is low and variable and is highly dependent on formulation and diet. Bioavailability of the suspension increases two-fold when administered with meals. When administered with food, bioavailability is approximately 47%. Without food, the bioavailability is 23%.
▧ Volume of Distribution :
* 0.60 ± 0.17 L/kg
▧ Protein binding :
Atovaquone is extensively bound to plasma proteins (99.9%) over the concentration range of 1 to 90 µg/mL.
▧ Metabolism :
Some evidence suggests limited metabolism (although no metabolites have been identified).
▧ Route of Elimination :
The half-life of atovaquone is long due to presumed enterohepatic cycling and eventual fecal elimination. There was little or no excretion of atovaquone in the urine (less than 0.6%).
▧ Half Life :
2.2 to 3.2 days
▧ Clearance :
* 10.4 +/- 5.5 ml/min [HIV-infected patients receiving IV administration]
Độc Tính : The median lethal dose is higher than the maximum oral dose tested in mice and rats (1825 mg/kg per day). Overdoses up to 31,500 mg of atovaquone have been reported. In one such patient who also took an unspecified dose of dapsone, methemoglobinemia occurred. Rash has also been reported after overdose.
Chỉ Định : For the treatment or prevention of Pneumocystis carinii pneumonia in patients who are intolerant to trimethoprim-sulfamethoxazole (TMP-SMX). Also indicated for the acute oral treatment of mild to moderate PCP in patients who are intolerant to TMP-SMX.
Tương Tác Thuốc :
  • Rifabutin Rifabutin decreases the effect of atovaquone
  • Rifampicin Rifampin may decrease the effect of atovaquone.
  • Tetracycline Tetracycline may decrease the effect of atovaquone.
  • Zidovudine Atovaquone increases the effect and toxicity of zidovudine
Liều Lượng & Cách Dùng : Suspension - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Malarone Pediatric
  • Công ty :
    Sản phẩm biệt dược : MEPRON
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