Tìm theo
Nitrofurantoin
Các tên gọi khác (3) :
  • 5-Nitrofurantoin
  • N-(5-Nitrofurfurylidene)-1-aminohydantoin
  • SID11112186
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 67-20-9
ATC: J01XE01
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C8H6N4O5
PTK: 238.157
A bacteriostatic or bactericidal agent depending on the concentration and susceptibility of the infecting organism. Nitrofurantoin is active against some gram positive organisms such as S. aureus, S. epidermidis, S. saprophyticus, Enterococcus faecalis, S. agalactiae, group D streptococci, viridians streptococci and Corynebacterium. Its spectrum of activity against gram negative organisms includes E. coli, Enterobacter, Neisseria, Salmonella and Shigella. It may be used as an alternative to trimethoprim/sulfamethoxazole for treating urinary tract infections though it may be less effective at eradicating vaginal bacteria. May also be used in females as prophylaxis against recurrent cystitis related to coitus. Nitrofurantoin is highly stable to the development of bacterial resistance, a property thought to be due to its multiplicity of mechanisms of action.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C8H6N4O5
Phân tử khối
238.157
Monoisotopic mass
238.033819322
InChI
InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3-
InChI Key
InChIKey=NXFQHRVNIOXGAQ-OQFOIZHKSA-N
IUPAC Name
1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
Traditional IUPAC Name
nitrofurantoin
SMILES
[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O
Độ tan chảy
223-228
Độ hòa tan
79.5 mg/L (at 24 °C)
logP
-0.47
logS
-2.8
pKa (strongest acidic)
9.23
pKa (Strongest Basic)
-2.2
PSA
120.73 Å2
Refractivity
53.11 m3·mol-1
Polarizability
19.75 Å3
Rotatable Bond Count
3
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
pKa
7.2
Dược Lực Học : Nitrofurantoin exhibits bacteriostatic or bactericidal effects by inhibiting the synthesis of DNA, RNA, protein and cell wall synthesis.
Cơ Chế Tác Dụng : A bacteriostatic or bactericidal agent depending on the concentration and susceptibility of the infecting organism. Nitrofurantoin is active against some gram positive organisms such as S. aureus, S. epidermidis, S. saprophyticus, Enterococcus faecalis, S. agalactiae, group D streptococci, viridians streptococci and Corynebacterium. Its spectrum of activity against gram negative organisms includes E. coli, Enterobacter, Neisseria, Salmonella and Shigella. It may be used as an alternative to trimethoprim/sulfamethoxazole for treating urinary tract infections though it may be less effective at eradicating vaginal bacteria. May also be used in females as prophylaxis against recurrent cystitis related to coitus. Nitrofurantoin is highly stable to the development of bacterial resistance, a property thought to be due to its multiplicity of mechanisms of action. Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that are thought to modulate and damage ribosomal proteins or other macromolecules, especially DNA, causing inhibition of DNA, RNA, protein, and cell wall synthesis. The overall effect is inhibition of bacterial growth or cell death.
Dược Động Học :
▧ Absorption :
Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug.
▧ Protein binding :
20-60% bound to plasma proteins
▧ Metabolism :
Partially metabolized in liver to aminofurantoin.
▧ Half Life :
0.3-1 hour
Độc Tính : Acute toxicity may cause vomiting. Adverse effects include nausea and urine discolouration. Rare hepatotoxic and hypersensitivity reactions have occurred. Hemolytic anemia is a risk in patients with G6PD deficiency. Ascending polyneuropathy may occur with prolonged therapy or in patients with low creatinine clearance.
Chỉ Định : May be used as an alternative in the treatment of urinary tract infections. May be used by females pericoitally for prophylaxis against recurrent cystitis related to coitus.
Liều Lượng & Cách Dùng : Capsule - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Goldshield
    Sản phẩm biệt dược : Furabid
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Furadantin
  • Công ty : Alvogen
    Sản phẩm biệt dược : Macrobid
  • Công ty : Goldshield
    Sản phẩm biệt dược : Macrodantin
  • Công ty :
    Sản phẩm biệt dược : Niftran
  • Công ty :
    Sản phẩm biệt dược : Siraliden
  • Công ty : Basel
    Sản phẩm biệt dược : Urantoin
  • Công ty : Thiemann
    Sản phẩm biệt dược : Urolong
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00698
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5353830
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504447
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00439
ChemSpider
http://www.chemspider.com/Chemical-Structure.4510228.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-1650-01
PharmGKB
http://www.pharmgkb.org/drug/PA450640
Wikipedia
http://en.wikipedia.org/wiki/Nitrofurantoin
RxList
http://www.rxlist.com/cgi/generic/nitro25m.htm
Drugs.com
http://www.drugs.com/nitrofurantoin.html
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