Ciprofloxacin
Systematic (IUPAC) name
1-cyclopropyl-6-fluoro-4-oxo- 7-piperazin-1-yl-quinoline-3-carboxylic acid
Identifiers
CAS number	85721-33-1
ATC code	J01MA02 S01AX13 S03AA07
PubChem	2764
DrugBank	APRD00424
Chemical data
Formula	C17H18FN3O3
Mol. weight	331.346
Pharmacokinetic data
Bioavailability	69%[1]
Metabolism	Hepatic, including CYP1A2
Half life	4 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	B3 (Australia), C (USA) The formula was drawn in bkchem and GIMP. File links The following pages link to this file: Ciprofloxacin Categories: Public domain images ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Metabolism (from Greek μεταβολισμός metabolismos) is the biochemical modification of chemical compounds in living organisms and cells. ... This page is a candidate for speedy deletion. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	Schedule 4 (Australia) Prescription Only (UK) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug (or POM Prescription Only Medicine, in UK) is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ...
Routes	Oral, intravenous, topical (ear drops, eye drops)

Ciprofloxacin is the generic international name for the synthetic antibiotic manufactured and sold by Bayer Pharmaceutical under the brand names Cipro® and Ciproxin® (and other brand names in other markets, e.g. veterinary drugs), belonging to a group called fluoroquinolones. Ciprofloxacin is bactericidal. Its mode of action depends upon blocking bacterial DNA replication by binding itself to an enzyme called DNA gyrase, thereby causing double-stranded breaks in the bacterial choromosome. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Ear drops are a form of medicine used to treat or prevent ear infections, especially infections of the outer ear and ear canal (Otitis externa). ... Eye drops are saline-containing drops used as a vector to administer medication in the eye. ... Staphylococcus aureus - Antibiotics Test plate. ... Bayer may also refer to Bayer Leverkusen. ... Quinolones and fluoroquinolones form a group of broad-spectrum antibiotics. ... A bacteriocide or bactericide is a substance that kills bacteria and, preferably, nothing else. ... In pharmacology, the term mechanism of action refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect. ... The general structure of a section of DNA Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the biological development of a cellular form of life or a virus. ... DNA replication. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Topoisomerases (Type I: EC 5. ...

Activity

Ciprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. A broad-spectrum antibiotic is so called due to its activity against a wide range of infectious agents. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ...

• Enterobacteriaceae
• Vibrio
• Haemophilus influenzae
• Neisseria gonorrhoeae
• Neisseria meningitidis
• Moraxella catarrhalis
• Brucella
• Campylobacter
• Mycobacterium intracellulare
• Legionella sp.
• Pseudomonas aeruginosa
• Bacillus anthracis - that causes anthrax

Weak activity against: Genera see text The Enterobacteriaceae are a large family of bacteria, including many of the more familiar pathogens, such as Salmonella and Escherichia coli. ... Vibrio is a genus of bacteria, included in the gamma subgroup of the Proteobacteria. ... Binomial name Haemophilus influenzae (Lehmann & Neumann 1896) Winslow 1917 Haemophilus influenzae, formerly called Pfeiffers bacillus or Bacillus influenzae, is a non-motile Gram-negative coccobacillus first described in 1892 by Dr. Richard Pfeiffer during an influenza pandemic. ... Binomial name Neisseria gonorrhoeae Zopf, 1885 Neisseria gonorrhoeae is a species of Gram-negative (see also Gram Stain) bacteria responsible for the disease gonorrhoea. ... Binomial name Neisseria meningitidis Albrecht & Ghon, 1901 Neisseria meningitidis, also simply known as meningococcus is a gram-negative bacterium best known for its role in meningitis. ... Moraxella catarrhalis is a gram-negative, aerobic, oxidase-positive diplococcus. ... Species Brucella melitensis Brucella abortus Brucella suis Brucella canis Brucella are a genus of bacteria. ... Species C. fetus C. jejuni Campylobacter is a genus of Gram-negative bacteria. ... Species Legionella adelaidensis Legionella anisa Legionella beliardensis Legionella birminghamensis Legionella bozemanii Legionella brunensis Legionella busanensis Legionella cherrii Legionella cincinnatiensis Legionella donaldsonii Legionella drancourtii Legionella drozanskii Legionella erythra Legionella fairfieldensis Legionella fallonii Legionella feeleii Legionella geestiana Legionella gratiana Legionella gresilensis Legionella hackeliae Legionella israelensis Legionella jamestowniensis Legionella jordanis Legionella lansingensis Legionella... Binomial name Pseudomonas aeruginosa (Schroeter 1872) Migula 1900 Pseudomonas aeruginosa is Gram-negative, aerobic, rod-shaped bacteria with unipolar motility. ... Binomial name Bacillus anthracis Cohn 1872 Bacillus anthracis is a Gram-positive, facultatively anaerobic, rod-shaped bacterium of the genus Bacillus. ...

• Streptococcus pneumoniae
• Chlamydia trachomatis
• Chlamydia pneumoniae

No activity against: Binomial name Streptococcus pneumoniae (Klein 1884) Chester 1901 Streptococcus pneumoniae is a species of Streptococcus that is a major human pathogen. ... Binomial name Chlamydia trachomatis Busacca, 1935 Chlamydia trachomatis is a species of the chlamydiae, a group of obligately intracellular bacteria. ... Binomial name Chlamydia pneumoniae Chlamydia pneumoniae is a obligate intracellular bacterium. ...

• Bacteroides
• Burkholderia cepacia
• Enterococcus faecium
• Ureaplasma urealyticum

• and others

The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics. Because of its general safety, potency and broad spectrum activity, ciprofloxacin was initially reserved as a "last-resort" drug for use on difficult and drug-resistant infections. As with any antibiotic, however, increasing time and usage has led to an increase in ciprofloxacin-resistant infections, mainly in the hospital setting. Also implicated in the rise of resistant bacteria is the use of lower-cost, less potent fluoroquinolones, and the widespread addition of ciprofloxacin and other antibiotics to the feed of farm animals, which leads to greater and more rapid weight gain, for reasons which are not clear. A genus of gram-negative, anaerobic, rod-shaped, non-sporeforming bacteria that occur in the respiratory, intestinal, and urogenital tracts of warm-blooded animals and include some pathogenic species. ... Burkholderia cepacia complex or simply Burkholderia cepacia is a group of catalase-producing, non-lactose-fermenting Gram-negative bacteria composed of at least seven different species, including Burkholderia multivorans, Burkholderia vietnamiensis, Burkholderia stabilis, and Burkholderia ambifaria. ... Binomial name Ureaplasma urealyticum Shepard et al. ... In medicine, an Adverse effect is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as a result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ... An antibiotic is a drug that kills or slows the growth of bacteria. ... Drugs of last resort are drugs with the most potent antibiotic, antiviral, or anticancer effect, and for which no (or for cancer, very few) resistant strains are known. ... Staphylococcus aureus - Antibiotics Test plate. ... A physician visiting the sick in a hospital. ... Quinolones and fluoroquinolones form a group of broad-spectrum antibiotics. ...

In cell culture it is used to treat infection with mycoplasma. Species M. genitalium M. hominis M. pneumoniae etc. ...

Label information

The drug is available for oral and parenteral use. It is used in lower respiratory infections (pneumonias), urinary tract infections, STDs, septicemias, Legionellosis and atypical Mycobacterioses. Dosage in respiratory infections is 500-1500 mg a day in 2 doses. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... While often used as a synonym for pneumonia, the rubric of lower respiratory tract infection can also be applied to other types of infection including lung abscess, acute bronchitis, and empyema. ... It has been suggested that CURB-65 be merged into this article or section. ... A urinary tract infection (UTI) is an infection of the urinary tract. ... Sexually transmitted diseases (STDs) — also known as sexually transmissible diseases, sexually transmitted infections (STIs) or (infrequently) venereal diseases (VD) or social disease — are diseases or infections that have a significant probability of transmission between humans by means of sexual contact, vaginal intercourse, oral sex, and/or anal sex. ... Sepsis (in Greek Σήψις) is a serious medical condition caused by a severe systemic infection leading to a systemic inflammatory response. ... Legionellosis is an infection caused by the genus of Gram negative bacteria Legionella, notably Legionella pneumophila. ...

It is contraindicated in children, pregnancy, and in patients with epilepsy. Dose adjustment or avoidance may be necessary with liver or renal failure. A pregnant woman near the end of her term Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... Liver failure is the final stage of liver disease. ... Renal failure is the condition in which the kidneys fail to function properly. ...

Ciprofloxacin can cause photosensitivity reactions and can elevate plasma theophylline levels to toxic values. It can also cause constipation and sensitivity to caffeine. Ciprofloxacin is also known to cause swelling of certain joints and cartilage. Photosensitivity is the amount to which an object reacts upon receiving photons of light. ... Theophylline is a methylxanthine drug used in therapy for respiratory diseases such as COPD or asthma under a variety of brand names. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to eliminate; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ...

Interactions

Quercetin, a flavonoid occasionally used as a dietary supplement may interact with fluroquinolones, as quercetin competitively binds to bacterial DNA gyrase. Some foods such as garlic and apples contain high levels of quercetin. Whether this inhibits or enhances the effect of fluoroquinolones is not entirely clear.^[2] Quercetin is a flavonoid that forms the backbone for many other flavonoids, including the citrus flavonoids rutin, hesperidin, naringin and tangeritin. ... Molecular structure of flavone The term flavonoid refers to a class of plant secondary metabolites based around a phenylbenzopyrone structure. ... A prescribed dietary supplement is intended to supply nutrients (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ...

Contraindications

Metal cations such as aluminium, magnesium, calcium, ferrous sulfate, and zinc are thought to form chelation complexes with fluoroquinolone antibiotics and prevent the drugs from being absorbed. Because of this, avoid taking antacids which contain aluminium, magnesium or calcium with ciprofloxacin. Sucralfate, which has a high aluminium content, also reduces the bioavailability of ciprofloxacin to approximately 4%^[3]. Ciprofloxacin may be taken with meals or on an empty stomach. Ciprofloxacin should not be taken with dairy products or calcium-fortified juices alone, but may be taken with a meal that contains these products.^[4] General Name, Symbol, Number aluminium, Al, 13 Chemical series poor metals Group, Period, Block 13, 3, p Appearance silvery Atomic mass 26. ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white Atomic mass 24. ... General Name, Symbol, Number calcium, Ca, 20 Chemical series alkaline earth metals Group, Period, Block 2, 4, s Appearance silvery white Atomic mass 40. ... Iron(II) sulfate (FeSO4) is an example of an ionic compound. ... General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ... An antacid is any substance, generally a base, which counteracts stomach acidity. ... Sucralfate is a prescription medication used to treat peptic ulcers. ...

Heavy exercise is discouraged, as achilles tendon rupture has been reported in patients taking ciprofloxacin. Achilles tendon rupture due to ciprofloxacin use is typically associated with renal failure. Achilles tendon rupture commonly occurs as an acceleration injury e. ... Chronic renal failure (CRF, or chronic kidney failure, CKF, or chronic kidney disease, CKD) is a slowly progressive loss of renal function over a period of months or years and defined as an abnormally low glomerular filtration rate, which is usually determined indirectly by the creatinine level in blood serum. ...

The toxicity of drugs that are metabolised by the cytochrome P450 system is enhanced by concomitant use of some quinolones. They may also interact with the GABA A receptor and cause neurological symptoms; this is further augmented by certain non-steroidal anti-inflammatory drugs.^[5] The GABAA receptor is one of the three ligand-gated ion channels responsible for mediating the effects of Gamma-AminoButyric Acid (GABA), the major inhibitory neurotransmitter in the brain. ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ...

Fluoroquinolones are increasingly contraindicated for patients who have been to S.E. Asia due to the growing prevalance of antibiotic resistance to the class of antibiotics in that region. ^[6]

Dosing

Ciprofloxacin is available in oral tablets (250, 500, 650, and 1000 mg), as well as ready-made infusion bottles (200 and 400 mg). A combination preparation of ciprofloxacin 500 mg and tinidazole 600 mg is marketed under the name Ciplox-TZ® for infections where anaerobes or protozoa together with ciprofloxacin-sensitive aerobes are likely. Tinidazole is a prescription drug used against protozoa infections. ...

Due to its elimination half-life, ciprofloxacin is administered twice daily. No dose adjustments are generally required for mild to moderate renal impairment.

Business aspects

The discovery and development of ciprofloxacin is that rare case of an actual groundbreaking new drug development, opening up an entire new class of antibiotics for further research, development, and marketing. Even more remarkable, it seems to be a case where the first drug discovered of this class remains the 'gold standard' in terms of efficacy, with the other drugs developed by other pharmaceutical companies relegated to 'me-too' status and forced to compete on the basis of lower cost. A pharmaceutical company is a licensed drug company, licensed to discover, develop, markets and distribute drugs. ...

Encouraged by the magnitude of this success, as well as the influx of cash, Bayer Pharmaceutical embarked on a plan to remake itself from a minor pharmaceutical manufacturer into a major player in the international pharmaceutical business, with a lock on the antibiotic field. Unfortunately, a combination of the tendency for antibiotics to be viewed as a commodity and prescribed on the basis of lowest cost, Bayer's inability to follow up with another 'blockbuster' discovery, and a general downturn in the international pharmaceutical business forced Bayer into a major downsizing in 2000-2001. Faced with the imminent expiry of its patent rights to ciprofloxacin in the early 2000's and the predictable loss of market share to generic ciprofloxacin, Bayer has resorted to the usual strategy of pharmaceutical companies in such a situation; focus on the development and patenting of new variations of the old drug (i.e. pediatric ciprofloxacin, intravenous ciprofloxacin, once-a-day ciprofloxacin, etc.), which will have the side effect of extending the patent on the original drug. Bayer may also refer to Bayer Leverkusen. ... Staphylococcus aureus - Antibiotics Test plate. ... An antibiotic is a drug that kills or slows the growth of bacteria. ... Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in 1863. ... Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in 1863. ... A patent is a set of exclusive rights granted by a government to an inventor or applicant for a limited amount of time (normally maximum 20 years from the filing date, depending on extension). ... Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in 1863. ... A pharmaceutical company is a licensed drug company, licensed to discover, develop, markets and distribute drugs. ...

"Cipro" became a household word during the 2001 anthrax attacks after the destruction of the World Trade Center. Bayer took a severe financial blow from the costs involved in rapidly increasing production of the drug to be sold to the American government at far below market price. (Redirected from 2001 anthrax attack) A letter sent to Senate Majority Leader Tom Daschle containing weaponised anthrax powder caused the deaths of two postal workers. ... World trade centers or world trade centres (usually abbreviated WTC) arose in the United States and Japan in the 1970s, spearheaded by New York Citys World Trade Center. ... Bayer AG (German pronunciation BYE-er, in US usually pronounced BAY-er) (NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in 1863. ...

Generic ciprofloxacin is now available in many markets around the world including the USA. In addition two new once daily formulations have been launched in the USA. Bayer have marketed Cipro XR® which is an extended release formulation. Meanwhile Depomed have developed ProQuin XR® another once daily formulation of ciprofloxacin which uses a gastric retention polymer technology to slow the release of ciprofloxacin into the blood.

Ciprofloxacin is the third largest selling molecule in Pakistan pharmaceutical market. It is marketed by numerous companies. In Pakistan, Highnoon Laboratories Ltd. markets the brand under the name "Cyrocin".

Footnotes

1. ^ Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J. Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother 1986;30:444-6. PMID 3777908.
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. PMID 8718602.
3. ^ Spivey JM, Cummings DM, Pierson NR. Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy 1996;16:314-6. PMID 8820479.
4. ^ Drug effects of Ciprofloxacin
5. ^ Brouwers JR. Drug interactions with quinolone antibacterials. Drug Saf 1992;7:268-81. PMID 1524699.
6. ^ Fluoroquinolone Resistance in Neisseria gonorrhoeae -- Colorado and Washington, 1995 [1]

External links

• Data sheet for Cipro
• Fluoroquinolone Toxicity Research Foundation querying the overall safety of fluoroquinolones
• Emergency Medicine Magzine a review of ciprofloxacin in relation to other fluoroquinolones