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Inhibits relaxation of DNA; inhibits DNA gyrase in susceptible organisms; promotes breakage of
double-stranded DNA
Absorption
Bioavailability (PO): ~50-85%
Peak plasma time (PO): Immediate-release, 0.5-2 hr; extended-release, 1-2.5 hr
Distribution
Distributed widely throughout body; tissue concentrations often exceed serum concentrations,
especially in kidneys, gallbladder, liver, lungs, gynecologic tissue, and prostatic tissue;
cerebrospinal fluid (CSF) concentration is 10% in noninflamed meninges and 14-37% in
inflamed meninges; crosses placenta; enters breast milk
Protein bound: 20-40%
Vd: 2.1-2.7 L/kg
Metabolism
Metabolized in liver
Enzyme inhibitor: CYP1A2
Elimination
Half-life: 2-5 hr (children); 3-5 hr (adults)
Excretion: Urine (30-50%), feces (15-43%)
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.
This radiopharmaceutical diagnostic imaging agent is being investigated for its ability to
uniquely detect and determine the location of bacterial infection in patients with difficult-todiagnose signs and symptoms. This may be of use with the potential diagnosis of infection,
Ciprofloxacin
DB00537 (APRD00424, EXPT00999)
Small Molecule
Approved, Investigational
A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]
Structure
Synonyms
External
Identifiers
Prescription
Products
entries
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3quinolinecarboxylic acid
1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3carboxylic acid
1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3carboxylic acid
1-CYCLOPROPYL-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline3-carboxylic acid
1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
1-Cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
1-Cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3quinolinecarboxylic acid
Ciprofloxacin
Ciprofloxacine
Ciprofloxacino
Ciprofloxacinum
Not Available
Show
Name
Dosage Strength
Route
Labeller
Actavis
Pharma
Company
Actavis
Act
tablet
500 mg oral
Pharma
Ciprofloxacin
Company
Actavis
Act
tablet
250 mg oral
Pharma
Ciprofloxacin
Company
AuroAuro Pharma
tablet
750 mg oral
ciprofloxacin
Inc
AuroAuro Pharma
tablet
500 mg oral
ciprofloxacin
Inc
AuroAuro Pharma
tablet
250 mg oral
ciprofloxacin
Inc
BioBiomed
tablet
500 mg oral
ciprofloxacin
Pharma
Alcon
Ciloxan
ointment 3.33 mg/g ophthalmic Laboratories,
Inc.
Alcon Canada
Ciloxan
solution 0.3 %
ophthalmic
Inc
Physicians
3.5
Ciloxan
solution
ophthalmic Total Care,
mg/mL
Inc.
Showing 1 to 10 of 142 entries
Act
tablet
Ciprofloxacin
Previous
15
750 mg
oral
Marketing Marketing
Start
End
2004-02-18
Not
applicable
2004-02-18
Not
applicable
2004-02-18
Not
applicable
Not
applicable
Not
2012-06-13
applicable
Not
2012-06-13
applicable
Not
Not
applicable applicable
2012-06-13
1998-06-02
Not
applicable
1992-12-31
Not
applicable
1995-07-10
Not
applicable
Next
Show
entries
Name
Dosage Strength
Route
Labeller
Apo-ciproflox tablet
500 mg
oral
Apotex Inc
Apo-ciproflox tablet
250 mg
oral
Apotex Inc
Apo-ciproflox tablet
oral
750 mg
tablet,
Ciprofloxacin film
500 mg/1 oral
coated
injection,
Ciprofloxacin
2 mg/mL intravenous
solution
tablet,
Ciprofloxacin film
coated
Ciprofloxacin
solution/ 3.5
drops
mg/mL
topical
tablet,
Ciprofloxacin film
coated
Ciprofloxacin tablet
Previous
Apotex Inc
Marketing Marketing
Start
End
Not
2004-02-09
applicable
Not
2004-02-09
applicable
Not
2005-09-14
applicable
Not
2004-02-09
applicable
Golden State
Not
Medical Supply, 2014-11-03
applicable
Inc
Not
Hospira, Inc.
2008-03-18
applicable
HHS/Program
Support
Not
2004-06-09
Center/Supply
applicable
Service Center
Medsource
Not
2008-03-20
Pharmaceuticals
applicable
Lake Erie
Medical DBA
Not
2013-05-02
Quality Care
applicable
Products LLC
Preferred
Not
Pharmaceuticals, 2015-01-29
applicable
Inc.
22
Next
Not
Availabl
e
Show
Previous
Next
Company
Brand mixtures
Show
entries
Name
Cipro
Labeller
Bayer Health Care
Pharmaceuticals Inc.
Ingredients
1. Ciprofloxacin
2. Ciprofloxacin
Name
Labeller
Ingredients
1. Ciprofloxacin
Cipro HC
1. Ciprofloxacin
Cipro HC Otic
Suspension
Ciprodex
2. Hydrocortisone
1. Ciprofloxacin
2. Dexamethasone
Ciprofloxacin
Ciprofloxacin
Extended-release
Mylan Pharmaceuticals
Inc.
1. Ciprofloxacin
2. Ciprofloxacin
1. Ciprofloxacin
Par Pharmaceutical, Inc.
2. Ciprofloxacin
Showing 1 to 6 of 6 entries
Previous
Next
Salts
Name/CAS
Ciprofloxa
cin
Hydrochlor
ide
93107-08-5
Structure
Properties
InChI Key:
DIOIOSKK
IYDRIQUHFFFAO
YSA-N
Monoisotop
ic Mass:
367.109897
Name/CAS
Structure
Properties
401
Anti-Infective Agents
Quinolones
Average
Mass:
367.802
Categories
UNII
CAS number
5E8K9I0O4U
85721-33-1
Average: 331.3415
Weight
Monoisotopic: 331.133219662
Chemical Formula C17H18FN3O3
InChI Key
InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N
InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6InChI
20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3IUPAC Name
carboxylic acid
SMILES
OC(=O)C1=CN(C2CC2)C2=CC(N3CCNCC3)=C(F)C=C2C1=O
Taxonomy
This compound belongs to the class of organic compounds known as
Description
quinoline carboxylic acids. These are quinolines in which the quinoline
ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
N-arylpiperazines
Fluoroquinolones
Hydroquinolones
Hydroquinolines
Pyridinecarboxylic acids
Dialkylarylamines
Fluorobenzenes
Aryl fluorides
Vinylogous amides
Heteroaromatic compounds
Dialkylamines
Carboxylic acids
Azacyclic compounds
Organofluorides
Hydrocarbon derivatives
Carbonyl compounds
Quinoline-3-carboxylic acid
N-arylpiperazine
Fluoroquinolone
Dihydroquinolone
Aminoquinoline
Dihydroquinoline
Substituents
Dialkylarylamine
Fluorobenzene
Benzenoid
Pyridine
Piperazine
1,4-diazinane
Aryl halide
Aryl fluoride
Heteroaromatic compound
Vinylogous amide
Tertiary amine
Azacycle
Secondary amine
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Molecular
Framework
External
Descriptors
Organohalogen compound
Carbonyl group
Amine
N-arylpiperazine (CHEBI:100241 )
aminoquinoline (CHEBI:100241 )
quinolone (CHEBI:100241 )
Pharmacology
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
Indication
and skin structure infections, bone and joint infections, complicated intraabdominal infections (used in combination with metronidazole), infectious
diarrhea, typhoid fever (enteric fever), uncomplicated cervical and
urethral gonorrhea, and inhalational anthrax (post-exposure).
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,
Pharmacodynamics
tetracyclines, or aminoglycosides; therefore, organisms resistant to these
drugs may be susceptible to ciprofloxacin. There is no known crossresistance between ciprofloxacin and other classes of antimicrobials.
Notably the drug has 100 times higher affinity for bacterial DNA gyrase
than for mammalian.
The bactericidal action of ciprofloxacin results from inhibition of the
Mechanism of
enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are
action
required for bacterial DNA replication, transcription, repair, strand
supercoiling repair, and recombination.
Absorption
Rapidly and well absorbed from the gastrointestinal tract after oral
Route of elimination
Half life
Clearance
Toxicity
Affected organisms
Pathways
SNP Mediated
Effects
SNP Mediated
Adverse Drug
Reactions
Not Available
20 to 40%
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.
Approximately 40 to 50% of an orally administered dose is excreted in the
urine as unchanged drug.
4 hours
Not Available
Not Available
Not Available
Menampilkan terjemahan untuk 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 anti infective 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.
Terjemahkan selain dari 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.
Indikasi Untuk pengobatan infeksi berikut disebabkan oleh organisme rentan: infeksi saluran
kemih, sistitis akut tanpa komplikasi, prostatitis bakteri kronis, infeksi saluran pernapasan
bawah, sinusitis akut, infeksi kulit dan struktur kulit, infeksi tulang dan sendi, infeksi intraabdomen rumit ( digunakan dalam kombinasi dengan metronidazole), infeksi diare, demam tifoid
(demam enterik), tidak rumit serviks dan uretra gonore, dan anthrax hirup (post-exposure).
Farmakodinamik Ciprofloxacin merupakan agen anti infeksi spektrum luas dari kelas
fluorokuinolon. Ciprofloxacin memiliki aktivitas in vitro terhadap berbagai gram-negatif dan
gram positif mikroorganisme. Mekanisme kerja dari kuinolon, termasuk ciprofloxacin, berbeda
dengan agen antimikroba lain seperti beta-laktam, makrolid, tetrasiklin, atau aminoglikosida;
Oleh karena itu, organisme resisten terhadap obat ini dapat mengalami ciprofloxacin. Tidak ada
dikenal resistansi silang antara ciprofloxacin dan kelas-kelas lain antimikroba. Terutama obat
memiliki afinitas 100 kali lebih tinggi untuk girase DNA bakteri daripada mamalia.
Mekanisme kerja Tindakan bakterisida hasil ciprofloxacin dari penghambatan enzim
topoisomerase II (DNA gyrase) dan topoisomerase IV, yang diperlukan untuk replikasi bakteri
DNA, transkripsi, perbaikan, untai perbaikan supercoil, dan rekombinasi.
Penyerapan Cepat dan baik diserap dari saluran pencernaan setelah pemberian oral.
Bioavailabilitas absolut adalah sekitar 70% tanpa kehilangan besar dengan metabolisme lulus
pertama.
http://www.drugbank.ca/drugs/DB00537#pharmacology