用户名： 密   码：
注册 | 忘记密码？
药品详细

Ciprofloxacin(环丙沙星)

化学结构式图
中文名
环丙沙星
英文名
Ciprofloxacin
分子式
C17H18FN3O3
化学名
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
分子量
Average: 331.3415
Monoisotopic: 331.133219662
CAS号
85721-33-1
ATC分类
J01M 未知;S03A 未知;S02A 未知;S01A 抗感染药
药物类型
small molecule
阶段
approved
商品名
Bacquinor;Baycip;Bernoflox;Ciflox;Cifloxin;Ciloxan;Ciprinol;Cipro;Cipro I.V.;Cipro XL;Cipro XR;Ciprobay;Ciprocinol;Ciprodar;Cipromycin;Ciproquinol;Ciproxan;Ciproxin;Flociprin;Floxin;Ocuflox;Proquin XR;Septicide;Velomonit;
同义名
ciprofloxacin;Ciprofloxacin dihydrochloride;Ciprofloxacin HCl;Ciprofloxacin hydrochloride;Ciprofloxacin monohydrochloride;Ciprofloxacina;
基本介绍

A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]

生产厂家
  • Acs dobfar info sa
  • Akorn inc
  • Alcon inc
  • Allergan inc
  • Apotex inc
  • App pharmaceuticals llc
  • Aurobindo pharma ltd
  • Barr laboratories inc
  • Bausch and lomb pharmaceuticals inc
  • Baxter healthcare corp
  • Bayer healthcare pharmaceuticals inc
  • Bayer pharmaceuticals corp
  • Bedford laboratories
  • Bedford laboratories div ben venue laboratories inc
  • Carlsbad technology inc
  • Claris lifesciences ltd
  • Depomed inc
  • Dr reddys laboratories ltd
  • Fdc ltd
  • Hikma farmaceutica (portugal) sa
  • Hikma pharmaceuticals
  • Hitech pharmacal corp
  • Hospira inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Nexus pharmaceuticals inc
  • Nostrum laboratories inc
  • Novex pharma
  • Pharmaforce inc
  • Pliva inc
  • Ranbaxy pharmaceuticals inc
  • Sandoz inc
  • Taro pharmaceuticals usa inc
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa inc
  • Unique pharmaceutical laboratories
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Wraser pharmaceuticals llc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. Pubmed
  2. Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. Pubmed
  3. Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. Pubmed
  4. Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Fluoroquinolones and Quinolones
  • Aminoquinolines and Derivatives
Substructures
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Pyridines and Derivatives
  • Piperazines
  • Fluoroquinolones and Quinolones
  • Cyclopropane and Derivatives
  • Benzene and Derivatives
  • Aminoquinolines and Derivatives
  • Carboxylic Acids and Derivatives
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
  • (Iso)quinolines and Derivatives
  • Aryl Halides
  • Anilines
适应症
antibacterials 抗细菌;
药理
Indication For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).
Pharmacodynamics Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. The mechanism of action of quinolones, including ciprofloxacin, is different from that of other antimicrobial agents such as beta-lactams, macrolides, tetracyclines, or aminoglycosides; therefore, organisms resistant to these drugs may be susceptible to ciprofloxacin. There is no known cross-resistance between ciprofloxacin and other classes of antimicrobials. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.
Mechanism of action The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.
Absorption Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.
Volume of distribution Not Available
Protein binding 20 to 40%
Metabolism
Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.
Route of elimination Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Half life 4 hours
Clearance
  • Renal cl=300 mL/min
Toxicity The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 255-257 °C Not Available
water solubility 3E+004 mg/L (at 20 °C) NOWARA,A ET AL. (1997)
logP 0.28 TAKACS-NOVAK,K ET AL. (1992)
pKa 6.09 TORNIANEN,K ET AL. (1996)
Predicted Properties
Property Value Source
water solubility 1.35e+00 g/l ALOGPS
logP -0.57 ALOGPS
logP -0.81 ChemAxon
logS -2.4 ALOGPS
pKa (strongest acidic) 5.76 ChemAxon
pKa (strongest basic) 8.68 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 72.88 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 87.94 ChemAxon
polarizability 33.12 ChemAxon
药物相互作用
Drug Interaction
Acenocoumarol The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of acenocoumarol.
Aluminium Formation of non-absorbable complexes
Aminophylline Ciprofloxacin may increase the effect of aminophylline.
Anisindione The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of anisindione.
Bendamustine Decreases metabolism, thus INCREASING levels of bendamustine. Decreased conversion of bendamustine to active metabolites. Concurrent administration of Ciproflaxacin or other CYP1A2 inhibitors may also increase the levels of bendamustine into active metabolites.
Caffeine Ciprofloxacin may increase the effect and toxicity of caffeine.
Calcium Formation of non-absorbable complexes
Calcium Acetate Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics such as ciprofloxacin. Of concern only with oral administration of both agents. Interactions can be minimized by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of an oral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones if administered with oral calcium supplements.
Clozapine Ciprofloxacin may increase clozapine serum levels
Cyclosporine Ciprofloxacin may increase the effect and toxicity of cyclosporine.
Dicumarol The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of dicumarol.
Dihydroxyaluminium Formation of non-absorbable complexes
Duloxetine Ciprofloxacin, a strong CYP1A2 inhibitor, may decrease the metabolism of duloxetine. Monitor for changes in the therapeutic and adverse effects of duloxetine if ciprofloxacin is initiated or discontinued.
Dyphylline Ciprofloxacin may increase the effect of dyphylline.
Eltrombopag Affects hepatic CYP1A2 metabolism, will increase effect/level of eltrombopag.
Ethotoin Decreases the hydantoin effect
Foscarnet Increased risk of convulsions
Iron Formation of non-absorbable complexes
Iron Dextran Formation of non-absorbable complexes
Lomitapide The effect of coadminstration of lomipatide with ciproflaxacin, and other moderate CYP3A4 inhibitors (such as aprepitant, amprenavir, atazanavir, ciprofloxacin, crizotinib, darunavir/ritonavir, diltiazem, erythromycin, fluconazole, fosamprenavir, imatinib, verapamil) is unknown. However, as coadministration is likely to increase serum concentrations of lomipatide, concomitant use is contraindicated.
Magnesium Formation of non-absorbable complexes
Magnesium oxide Formation of non-absorbable complexes
Mephenytoin Decreases the hydantoin effect
Methotrexate Ciprofloxacine may decrease the metabolism of methotrexate. Monitor for changes adverse effects of methotrexate if ciprofloxacin is initiated.
Oxtriphylline Ciprofloxacin may increase the effect of oxtriphylline.
Phenytoin Ciprofloxacin may decrease the therapeutic effect of phenytoin.
Procainamide Ciprofloxacin may increase the effect of procainamide.
Ramelteon Ciprofloxacin increases levels/toxicity of ramelteon
Rasagiline Ciprofloxacin, a strong CYP1A2 inhibitor, may decrease the metabolism of rasagiline. Monitor for changes in the therapeutic and adverse effects of rasagiline if ciprofloxacin is initiated or discontinued.
Ropinirole Ciprofloxacin may increase the effect and toxicity of ropinirole.
Sevelamer Sevelamer decreases ciprofloxacin bioavailability
Sildenafil Ciprofloxacin may increase the serum level of sildenafil.
Sucralfate Formation of non-absorbable complexes
Tacrine The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by strong CYP1A2 inhibitors such as Ciprofloxacin. Consider modifying therapy to avoid Tacrine toxicity. Monitor the efficacy and toxicity of Tacrine if Ciprofloxacin is initiated, discontinued or if the dose is changed.
Theophylline Ciprofloxacin may increase the effect of theophylline.
Thiothixene The strong CYP1A2 inhibitor, Ciprofloxacin, may decrease the metabolism and clearance of Thiothixene, a CYP1A2 substrate. Consider alternate therapy or monitor for changes in Thiothixene therapeutic and adverse effects if Ciprofloxacin is initiated, discontinued or dose changed.
Tizanidine Ciprofloxacin inhibits the metabolism and clearance of Tizanidine. Concomitant therapy is contraindicated.
Warfarin The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of warfarin.
Zinc Formation of non-absorbable complexes
食物相互作用
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid milk, calcium containing dairy products, iron, magnesium, zinc, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take with a full glass of water.
  • Take without regard to meals.

返回 | 收藏