Tìm theo
Grepafloxacin
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 119914-60-2
ATC: J01MA11
ĐG : GlaxoSmithKline Inc. , http://www.gsk.com
CTHH: C19H22FN3O3
PTK: 359.3947
Grepafloxacin is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C19H22FN3O3
Phân tử khối
359.3947
Monoisotopic mass
359.16451979
InChI
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
InChI Key
InChIKey=AIJTTZAVMXIJGM-UHFFFAOYSA-N
IUPAC Name
1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional IUPAC Name
grepafloxacin
SMILES
CC1CN(CCN1)C1=C(F)C(C)=C2C(=O)C(=CN(C3CC3)C2=C1)C(O)=O
Độ hòa tan
6.32e-01 g/l
logP
2.9
logS
-2.8
pKa (strongest acidic)
5.88
pKa (Strongest Basic)
8.77
PSA
72.88 Å2
Refractivity
97.4 m3·mol-1
Polarizability
37.69 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
6
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms.
Cơ Chế Tác Dụng : Grepafloxacin is an oral broad-spectrum quinoline antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death. [Wikipedia] Grepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA.
Dược Động Học :
▧ Absorption :
Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%.
▧ Protein binding :
50%
▧ Metabolism :
Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity
▧ Half Life :
15 ± 3 hours
Độc Tính : Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events.
Chỉ Định : For treatment of adults with mild to moderate infections caused by susceptible strains of Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis.
Tương Tác Thuốc :
  • Aluminium Formation of non-absorbable complexes
  • Aminophylline Grepafloxacin may increase the effect of aminophylline.
  • Amiodarone Increased risk of cardiotoxicity and arrhythmias
  • Amitriptyline Increased risk of cardiotoxicity and arrhythmias
  • Amoxapine Increased risk of cardiotoxicity and arrhythmias
  • Astemizole Increased risk of cardiotoxicity and arrhythmias
  • Bepridil Increased risk of cardiotoxicity and arrhythmias
  • Bretylium Increased risk of cardiotoxicity and arrhythmias
  • Caffeine Grepafloxacin may increase the effect and toxicity of caffeine.
  • Calcium Calcium may decrease the absorption of grepafloxacin. Doses should be spaced apart by at least 2 hours.
  • Chlorpromazine Increased risk of cardiotoxicity and arrhythmias
  • Clomipramine Increased risk of cardiotoxicity and arrhythmias
  • Desipramine Increased risk of cardiotoxicity and arrhythmias
  • Dihydroquinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
  • Disopyramide Increased risk of cardiotoxicity and arrhythmias
  • Doxepin Increased risk of cardiotoxicity and arrhythmias
  • Dyphylline Grepafloxacin may increase the effect of dyphylline.
  • Eltrombopag Affects hepatic enzyme CYP1A2 metabolism and may increase the level of eltrombopag.
  • Erythromycin Increased risk of cardiotoxicity and arrhythmias
  • Fluphenazine Increased risk of cardiotoxicity and arrhythmias
  • Imipramine Increased risk of cardiotoxicity and arrhythmias
  • Iron Formation of non-absorbable complexes
  • Iron Dextran Formation of non-absorbable complexes
  • Josamycin Increased risk of cardiotoxicity and arrhythmias
  • Magnesium Magnesium may decrease the absorption of grepafloxacin. Doses should be spaced apart by at least 2 hours.
  • Magnesium oxide Formation of non-absorbable complexes
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Methotrimeprazine Increased risk of cardiotoxicity and arrhythmias
  • Nortriptyline Increased risk of cardiotoxicity and arrhythmias
  • Oxtriphylline Grepafloxacin may increase the effect of oxtriphylline.
  • Perphenazine Increased risk of cardiotoxicity and arrhythmias
  • Prochlorperazine Increased risk of cardiotoxicity and arrhythmias
  • Promazine Increased risk of cardiotoxicity and arrhythmias
  • Promethazine Increased risk of cardiotoxicity and arrhythmias
  • Propiomazine Increased risk of cardiotoxicity and arrhythmias
  • Protriptyline Increased risk of cardiotoxicity and arrhythmias
  • Quinidine Increased risk of cardiotoxicity and arrhythmias
  • Quinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
  • Quinupristin This combination presents an increased risk of toxicity
  • Sotalol Increased risk of cardiotoxicity and arrhythmias
  • Sucralfate Formation of non-absorbable complexes
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Theophylline Grepafloxacin may increase the effect of theophylline.
  • Thiethylperazine Increased risk of cardiotoxicity and arrhythmias
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Trifluoperazine Increased risk of cardiotoxicity and arrhythmias
  • Triflupromazine Increased risk of cardiotoxicity and arrhythmias
  • Trimipramine Increased risk of cardiotoxicity and arrhythmias
  • Zinc Formation of non-absorbable complexes
Liều Lượng & Cách Dùng : Tablet, film coated - Oral
Dữ Kiện Thương Mại
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00365
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=72474
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507253
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C11368
ChemSpider
http://www.chemspider.com/Chemical-Structure.65391.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50117924
PharmGKB
http://www.pharmgkb.org/drug/PA449812
Wikipedia
http://en.wikipedia.org/wiki/Grepafloxacin
RxList
http://www.rxlist.com/cgi/generic2/grepa.htm
Drugs.com
http://www.drugs.com/mtm/grepafloxacin.html
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