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 Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death.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

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

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 Grepafloxacin was withdrawn in the United States due to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death.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

Công ty : Glaxo Wellcome

Sản phẩm biệt dược : Raxar

Đóng gói

Công ty : GlaxoSmithKline Inc.

Website : http://www.gsk.com

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

Bạn thấy hài lòng ?

Bạn chưa hài lòng ?

... loading