Tìm theo
Pyrazinamide
Các tên gọi khác (15 ) :
  • 2-carbamylpyrazine
  • 2-pyrazinecarboxamide
  • Aldinamide
  • Pirazinamida
  • Pirazinamide
  • Pyrazinamid
  • Pyrazinamida
  • Pyrazinamide
  • Pyrazinamidum
  • Pyrazine carboxamide
  • pyrazine-2-carboxamide
  • Pyrazineamide
  • Pyrazinecarboxamide
  • Pyrazinoic acid amide
  • Pyrizinamide
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 98-96-4
ATC: J04AK01
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C5H5N3O
PTK: 123.1127
A pyrazine that is used therapeutically as an antitubercular agent.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C5H5N3O
Phân tử khối
123.1127
Monoisotopic mass
123.043261797
InChI
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChI Key
InChIKey=IPEHBUMCGVEMRF-UHFFFAOYSA-N
IUPAC Name
pyrazine-2-carboxamide
Traditional IUPAC Name
pyrazinamide
SMILES
NC(=O)C1=NC=CN=C1
Độ tan chảy
192 °C
Độ hòa tan
1.5E+004 mg/L (at 25 °C)
logP
-0.60
logS
-0.91
pKa (strongest acidic)
13.06
pKa (Strongest Basic)
-0.68
PSA
68.87 Å2
Refractivity
30.45 m3·mol-1
Polarizability
11.13 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
pKa
-0.5
Dược Lực Học : Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.
Cơ Chế Tác Dụng : A pyrazine that is used therapeutically as an antitubercular agent. Pyrazinamide diffuses into M. tuberculosis, where the enzyme pyrazinamidase converts pyrazinamide to the active form pyrazinoic acid. Under acidic conditions, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted (PMID: 11914348). However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids (PMID: 17101678). This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I (PMID: 17485499). It has also been suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria (PMID: 21835980).
Dược Động Học :
▧ Absorption :
Rapidly and well absorbed from the gastrointestinal tract.
▧ Protein binding :
~10% (bound to plasma proteins)
▧ Metabolism :
Hepatic.
▧ Route of Elimination :
Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours
▧ Half Life :
9-10 hours (normal conditions)
Độc Tính : Side effects include liver injury, arthralgias, anorexia, nausea and vomiting, dysuria,malaise and fever, sideroblastic anemia, adverse effects on the blood clotting mechanism or vascular integrity, and hypersensitivity reactions such as urticaria, pruritis and skin rashes.
Chỉ Định : For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.
Tương Tác Thuốc :
  • Cyclosporine Pyrazinamide decreases the effect of cyclosporine
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Pyrazinamide 500 mg tablet
    Giá bán buôn : USD >1.26
    Đơn vị tính : tablet
  • Biệt dược thương mại : Rifater tablet
    Giá bán buôn : USD >3.1
    Đơn vị tính : tablet
Nhà Sản Xuất
  • Công ty : Bracco
    Sản phẩm biệt dược : Piraldina
  • Công ty : Armoxindo
    Sản phẩm biệt dược : Prazina
  • Công ty : Riemser
    Sản phẩm biệt dược : Pyrafat
  • Công ty : Sanofi-Aventis
    Sản phẩm biệt dược : Pyrazide
  • Công ty : Valeant
    Sản phẩm biệt dược : Tebrazid
  • Công ty : Orion
    Sản phẩm biệt dược : Tisamid
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00339
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=1046
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507478
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C01956
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00144
ChemSpider
http://www.chemspider.com/Chemical-Structure.1017.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/55806-012-02
PharmGKB
http://www.pharmgkb.org/drug/PA451182
Wikipedia
http://en.wikipedia.org/wiki/Pyrazinamide
RxList
http://www.rxlist.com/pyrazinamide-drug.htm
Drugs.com
http://www.drugs.com/cdi/pyrazinamide.html
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