Tìm theo
Temozolomide
Các tên gọi khác (22 ) :
  • 3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-D)(1,2,3,5)tetrazine-8-carboxamide
  • 3,4-dihydro-3-Methyl-4-oxoimidazo(5,1-D)-1,2,3,5-tetrazine-8-carboxamide
  • 3,4-dihydro-3-Methyl-4-oxoimidazo(5,1-D)-as-tetrazine-8-carboxamide
  • 8-Carbamoyl-3-methylimidazo(5,1-D)-1,2,3,5-tetrazin-4(3H)-one
  • BRN 5547136
  • CCRG 81045
  • CCRG-81045
  • CCRIS 8996
  • m & b 39831
  • M&B 39831
  • MB 39831
  • Methazolastone
  • NSC 362856
  • Sch 52365
  • Temodal
  • Temodar
  • Temozolodida
  • Temozolomid
  • Temozolomida
  • Témozolomide
  • Temozolomidum
  • TMZ
Thuốc điều trị ung thư
Thuốc Gốc
Small Molecule
CAS: 85622-93-1
ATC: L01AX03
ĐG : Baxter International Inc. , http://www.baxter.com
CTHH: C6H6N6O2
PTK: 194.1508
Temozolomide (Temodar and Temodal) is an oral alkylating agent used for the treatment of refractory anaplastic astrocytoma -- a type of cancerous brain tumor. Temozolomide is not active until it is converted at physiologic pH to the active form, 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (MTIC).
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C6H6N6O2
Phân tử khối
194.1508
Monoisotopic mass
194.055223466
InChI
InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
InChI Key
InChIKey=BPEGJWRSRHCHSN-UHFFFAOYSA-N
IUPAC Name
3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide
Traditional IUPAC Name
temozolomide
SMILES
CN1N=NC2=C(N=CN2C1=O)C(N)=O
Độ tan chảy
212 °C
Độ hòa tan
5.09e+00 g/l
logP
-2.8
logS
-1.6
pKa (strongest acidic)
10.51
pKa (Strongest Basic)
-3.6
PSA
105.94 Å2
Refractivity
47.86 m3·mol-1
Polarizability
16.88 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
5
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Temozolomide is an imidazotetrazine deritave and an antineoplastic agent. It is a prodrug that has little to no pharmacological activity until it is hydrolyzed in vivo to 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (MTIC). After administration, temozolomide undergoes rapid, nonenzymatic hydrolysis at physiological pH to MTIC, which is the active form of the drug. MTIC is generated through the effect of water at the highly electropositive C4 position of temozolomide, causing the ring of temozolomide to open, release carbon dioxide, and generate MTIC.
Cơ Chế Tác Dụng : Temozolomide (Temodar and Temodal) is an oral alkylating agent used for the treatment of refractory anaplastic astrocytoma -- a type of cancerous brain tumor. Temozolomide is not active until it is converted at physiologic pH to the active form, 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (MTIC). Temozolomide is not active until it is converted at physiologic pH to MTIC. It is suggested that MTIC then alkylates DNA at the N7 position of guanine, O3 position of adenosine, and O6 position of guanosine, with the most common site being the N7 position. This methylation of guanine residues lead to single and double-strand DNA breaks and subsequent apoptotic cell death. It is suggested that the N7-methylguanine plays a critical role in the antitumor activity of the drug, as there is a correlation between the sensitivity of tumor cell lines to temozolomide and the activity of O6-alkylguanine alkyltransferase, which is the DNA repair protein that specifically removes alkyl groups at the O6 position of guanine. Cells lines that have lower levels of AGT are more sensitive to the cytotoxicity of temozolomide. It is also suggested that cytotoxic mechanism of temozolomide is related to the failure of the DNA MMR system to find a complementary base for methylated guanine. The DNA MMR system is involved in the formation of a number of proteins that remove methylated guanine. Evidence shows that when this repair process is targeted to the DNA strand opposite the O6-methylguanine, its inability to find the correct target leads to long-lived nicks in the DNA. The accumulation of these nicks lead to the inhibition of replication in the daughter cells, thereby blocking the cell cycle at the G2-M boundary.
Dược Động Học :
▧ Absorption :
Rapid and complete absorption in the gastrointestinal tract
▧ Volume of Distribution :
* 0.4 L/kg
▧ Protein binding :
15%
▧ Route of Elimination :
About 38% of the administered temozolomide total radioactive dose is recovered over 7 days: 37.7% in urine and 0.8% in feces.
▧ Half Life :
Approximately 1.8 hours.
▧ Clearance :
* 5.5 L/hr/m2
Chỉ Định : For the treatment of adult patients diagnosed with anaplastic astrocytoma whose disease has progressed after therapy with nitrosourea and procarbazine, as well as concomitantly with radiation therapy for treatment of newly diagnosed glioblastoma multiforme. Also used as maintenance therapy for glioblastoma multiforme.
Tương Tác Thuốc :
  • Natalizumab The immunosuppressant, Temozolomide, may increase the adverse effects of Natalizumab. Increased risk of Progressive Multifocal Leukoencephalopathy (PML) and other infections. Concurrent therapy should be avoided.
  • Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Liều Lượng & Cách Dùng : Capsule - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Temodar 5 mg capsule
    Giá bán buôn : USD >10.84
    Đơn vị tính : capsule
  • Biệt dược thương mại : Temodar 20 mg capsule
    Giá bán buôn : USD >44.62
    Đơn vị tính : capsule
  • Biệt dược thương mại : Temodar 100 mg capsule
    Giá bán buôn : USD >223.07
    Đơn vị tính : capsule
  • Biệt dược thương mại : Temodar 180 mg capsule
    Giá bán buôn : USD >401.53
    Đơn vị tính : capsule
  • Biệt dược thương mại : Temodar 250 mg capsule
    Giá bán buôn : USD >466.11
    Đơn vị tính : capsule
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00853
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5394
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507934
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D06067
ChemSpider
http://www.chemspider.com/Chemical-Structure.5201.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50034562
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0085-3004-02
PharmGKB
http://www.pharmgkb.org/drug/PA451609
Wikipedia
http://en.wikipedia.org/wiki/Temozolomide
RxList
http://www.rxlist.com/cgi/generic2/temoz.htm
Drugs.com
http://www.drugs.com/cdi/temozolomide.html
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