Mechanism of Action

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,

including fever of unknown origin, osteomyelitis, wound infection, abdominal abscess,

pneumonia, appendicitis and tuberculosis.
Ciprofloxacin is a synthetic broad spectrum fluoroquinolone antibiotic. Ciprofloxacin binds to
and inhibits bacterial DNA gyrase, an enzyme essential for DNA replication. This agent is more
active against Gram-negative bacteria than Gram-positive bacteria. (NCI04)
https://pubchem.ncbi.nlm.nih.gov/compound/ciprofloxacin#section=Pharmacology

Menampilkan terjemahan untuk 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. 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-to-diagnose signs and symptoms. This may be of use with the potential
diagnosis of infection, including fever of unknown origin, osteomyelitis, wound infection,
abdominal abscess, pneumonia, appendicitis and tuberculosis. Ciprofloxacin is a synthetic broad
spectrum fluoroquinolone antibiotic. Ciprofloxacin binds to and inhibits bacterial DNA gyrase,
an enzyme essential for DNA replication. This agent is more active against Gram-negative
bacteria than Gram-positive bacteria. (NCI04)
Terjemahkan selain dari 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-to-diagnose signs and symptoms. This may be of use with the potential
diagnosis of infection, including fever of unknown origin, osteomyelitis, wound infection,
abdominal abscess, pneumonia, appendicitis and tuberculosis. Ciprofloxacin is a synthetic broad
spectrum fluoroquinolone antibiotic. Ciprofloxacin binds to and inhibits bacterial DNA gyrase,
an enzyme essential for DNA replication. This agent is more active against Gram-negative
bacteria than Gram-positive bacteria. (NCI04)
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.

Agen pencitraan diagnostik ini radiofarmaka sedang diselidiki karena kemampuannya untuk
mendeteksi unik dan menentukan lokasi infeksi bakteri pada pasien dengan tanda dan gejala
sulit-untuk-mendiagnosis. Ini mungkin digunakan dengan diagnosis potensi infeksi, termasuk
demam yang tidak diketahui, osteomyelitis, infeksi luka, abses perut, radang paru-paru, usus
buntu dan TBC.
Ciprofloxacin adalah spektrum yang luas fluorokuinolon antibiotik sintetis. Ciprofloxacin
mengikat dan menghambat bakteri girase DNA, sebuah penting enzim untuk replikasi DNA.
Agen ini lebih aktif terhadap bakteri Gram-negatif daripada bakteri Gram-positif. (NCI04)
Identification
Name
Accession Number
Type
Groups
Description

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

Generic Prescription Products

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 solution 0.3 %

ophthalmic 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

500 mg/1 oral

solution/ 3.5
drops
mg/mL

topical

tablet,
Ciprofloxacin film
coated

250 mg/1 oral

Ciprofloxacin tablet

250 mg/1 oral

Showing 1 to 10 of 214 entries

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

Over the Counter Products

International Brands
entries
Name
Bacquinor Not Available
Baycip
Not Available
Ciflox
Not Available
Cifloxin
Not Available
Ciprinol
Not Available
Ciprobay
Not Available
Ciprocinol Not Available
Ciprodar
Not Available
Ciproxan
Not Available
Ciproxin
Not Available
Showing 1 to 10 of 12 entries

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

Alcon Laboratories, Inc.

2. Hydrocortisone

1. Ciprofloxacin

Cipro HC Otic
Suspension

Alcon Canada Inc

Ciprodex

Alcon Laboratories, Inc.

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

Aminoquinolines and derivatives

Hydroquinolines

Pyridinecarboxylic acids

Dialkylarylamines

Fluorobenzenes

Aryl fluorides

Vinylogous amides

Heteroaromatic compounds

Monocarboxylic acids and derivatives

Dialkylamines

Carboxylic acids

Azacyclic compounds

Organofluorides

Hydrocarbon derivatives

Carbonyl compounds

Quinoline-3-carboxylic acid

N-arylpiperazine

Fluoroquinolone

Dihydroquinolone

Aminoquinoline

Dihydroquinoline

Pyridine carboxylic acid or derivatives

Substituents

Pyridine carboxylic acid

Dialkylarylamine

Fluorobenzene

Benzenoid

Pyridine

Piperazine

1,4-diazinane

Aryl halide

Aryl fluoride

Heteroaromatic compound

Vinylogous amide

Tertiary amine

Azacycle

Secondary amine

Monocarboxylic acid or derivatives

Secondary aliphatic amine

Carboxylic acid

Carboxylic acid derivative

Hydrocarbon derivative

Organooxygen compound

Organonitrogen compound

Organofluoride

Molecular
Framework

External
Descriptors

Organohalogen compound

Carbonyl group

Amine

Aromatic heteropolycyclic compound

Aromatic heteropolycyclic compounds

organofluorine compound (CHEBI:100241 )

N-arylpiperazine (CHEBI:100241 )

aminoquinoline (CHEBI:100241 )

quinolone (CHEBI:100241 )

quinolinemonocarboxylic acid (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

administration. The absolute bioavailability is approximately 70% with no

substantial loss by first pass metabolism.
Volume of
distribution
Protein binding
Metabolism

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

Renal cl=300 mL/min

The major adverse effect seen with use of is gastrointestinal irritation,

common with many antibiotics.

Enteric bacteria and other eubacteria

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