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"Cipro" redirects here. For the Rome Metro station, see Cipro (Rome Metro). Cipro (formerly Cipro - Musei Vaticani) is an underground station on Line A of the Rome Metro inaugurated in 1999
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. mass 331. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug 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 The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Fluorine, fluorum meaning "to flow" is the Chemical element with the symbol F and Atomic number 9 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 346
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 69%[1]
Metabolism Hepatic, including CYP1A2
Half life 4 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

B3(AU) C(US)
Legal status

Prescription Only (S4)(AU) POM(UK)
Routes Oral, intravenous, topical (ear drops, eye drops)

Ciprofloxacin is the generic international name for the synthetic antibiotic manufactured and sold by Bayer A.G. under the brand names Cipro, Ciproxin and Ciprobay (and other brand names in other markets, e. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems Cytochrome P450 1A2 (abbreviated CYP1A2) a member of the Cytochrome P450 mixed-function oxidase system is involved in the metabolism of Xenobiotics The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials 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 For a topic outline on this subject see List of basic Australia topics. The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located In Pharmacology and Toxicology, a route In Pharmacology and Toxicology, a route Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. In Medicine, a topical Medication is applied to body surfaces such as the Skin or Mucous membranes for example the Vagina 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. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German g. Veterinary medicine), belonging to a group called fluoroquinolones. Veterinary medicine the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife The quinolones are a family of synthetic Broad-spectrum antibiotics. Ciprofloxacin is bacteriocidal. A bactericide or bacteriocide is a substance that kills bacteria and preferably nothing else 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 chromosome. In Pharmacology, the term mechanism of action (MOA refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known DNA replication is the process of copying a double-stranded DNA molecule to form two double-stranded molecules Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins DNA gyrase, often referred to simply as gyrase, is a type II Topoisomerase ( that introduces negative Supercoils (or relaxes positive supercoils into DNA

Contents

Activity

Ciprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. The term broad-spectrum antibiotic refers to an Antibiotic with activity against a wide range of disease-causing Bacteria. Gram-positive bacteria are those that are stained dark blue or violet by Gram staining. Gram-negative bacteria are those Bacteria that do not retain Crystal violet dye in the Gram staining protocol It functions by inhibiting DNA gyrase, a type II topoisomerase, which is an enzyme necessary to separate replicated DNA, thereby inhibiting cell division. DNA gyrase, often referred to simply as gyrase, is a type II Topoisomerase ( that introduces negative Supercoils (or relaxes positive supercoils into DNA Topoisomerases (type I, type II) are Isomerase Enzymes that act on the topology of DNA. It is effective against:

Weak activity against:

No activity against:

The major adverse effect seen with use is gastrointestinal irritation, common with many antibiotics. Pseudomonas aeruginosa is a Gram-negative, aerobic, rod-shaped Bacterium with unipolar motility. Bacillus anthracis is a Gram-positive, facultatively anaerobic, rod-shaped Bacterium of the genus Bacillus. Streptococcus pneumoniae, or pneumococcus, is a Gram-positive, alpha-hemolytic diplococcus aerotolerant anaerobe and a member of the Genus Chlamydia trachomatis, an obligate intracellular human pathogen is one of three bacterial species in the genus Chlamydia, family Chlamydiaceae Bacteroides is a Genus of Gram-negative, bacillis bacteria. Bacteroides species are non- Endospore -forming anaerobes Burkholderia cepacia complex (BCC, or simply Burkholderia cepacia is a group of Catalase -producing non- Lactose - fermenting Enterococcus faecium is a Gram positive Bacterium in the genus Enterococcus. Ureaplasma urealyticum is a Bacterium belonging to the family Mycoplasmataceae. Streptococcus pyogenes is a spherical Gram-positive Bacteria that grows in long chains and is the cause of Group A streptococcal infections In Medicine, an adverse effect is a harmful and undesired effect resulting from a medication or other intervention such as Chemotherapy or Surgery. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa Because of its general safety, potency and broad spectrum activity, ciprofloxacin was initially reserved as a drug of last resort for use on difficult and antibiotic-resistant infections. The term broad-spectrum antibiotic refers to an Antibiotic with activity against a wide range of disease-causing Bacteria. Drugs of last resort are drugs only used when all other options are exhausted Antibiotic resistance is the ability of a Microorganism to withstand the effects of Antibiotics. As with any antibiotic, however, increasing time and usage has led to an increase in ciprofloxacin-resistant infections, mainly in the hospital setting. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa A hospital is an institution for Health care providing treatment by specialised staff and equipment and often but not always providing for 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. Antibiotic resistance is the ability of a Microorganism to withstand the effects of Antibiotics. The quinolones are a family of synthetic Broad-spectrum antibiotics.

In cell culture it is used to treat infection with mycoplasma. Mycoplasma is a Genus of bacteria which lack a Cell wall. Without a cell wall they are unaffected by many common Antibiotics such

Use against chlamydia and mycoplasma infections is now contraindicated; ciprofloxacin appears to be ineffective against these organisms, merely stopping their growth (and allowing them to resume growth after the antibiotic is withdrawn) rather than killing them. Mycoplasma is a Genus of bacteria which lack a Cell wall. Without a cell wall they are unaffected by many common Antibiotics such [2]

Label information

The drug is available for oral, parenteral and topical use. In Pharmacology and Toxicology, a route It is used in lower respiratory infections (pneumonias), urinary tract infections, STDs, septicemias, Legionellosis and atypical Mycobacteria. 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 Pneumonia is an inflammatory illness of the Lung. Frequently it is described as lung Parenchyma / alveolar inflammation and abnormal A urinary tract infection ( UTI) is a bacterial Infection that affects any part of the Urinary tract. A sexually transmitted disease ( STD) or venereal disease ( VD) is an illness that has a significant probability of transmission between Humans Sepsis is a serious medical condition characterized by a whole-body inflammatory state (called a Systemic inflammatory response syndrome or SIRS caused Legionellosis is an Infectious disease caused by Bacteria belonging to the Genus Legionella. Mycobacterium is a Genus of Actinobacteria, given its own family the Mycobacteriaceae Dosage in Respiratory tract infection is 500-1500 mg a day in 2 doses.

It is contraindicated in children (except for serious infections and anthrax post-exposure), pregnancy, and in patients with epilepsy. Anthrax is an acute Disease in humans and animals caused by the bacterium Bacillus anthracis which is highly lethal in some forms Pregnancy ( Latin graviditas) is the carrying of one or more offspring known as a Fetus or Embryo, inside the Uterus of a Female Epilepsy is a common chronic Neurological disorder that is characterized by recurrent unprovoked seizures. Dose adjustment or avoidance may be necessary with liver or renal failure. Liver failure is the inability of the Liver to perform its normal synthetic and metabolic function as part of normal physiology Renal failure or kidney

Ciprofloxacin can cause photosensitivity reactions and can elevate plasma theophylline levels to toxic values. Photosensitivity is the amount to which an object reacts upon receiving Photons especially Visible light. Theophylline, also known as dimethylxanthine, is a Methylxanthine drug used in therapy for Respiratory diseases such as COPD or Asthma It can also cause constipation and sensitivity to caffeine. Constipation, costiveness, or irregularity, is a condition of the Digestive system in which a person (or animal experiences hard Feces that Caffeine is a bitter white crystalline Xanthine Alkaloid that acts as a Psychoactive Stimulant Drug and a mild Diuretic Ciprofloxacin is also known to cause swelling of joints and cartilage, and cause tendon rupture and chronic pain.

Interactions

Quercetin, a flavonoid occasionally used as a dietary supplement may interact with fluoroquinolones, as quercetin competitively binds to bacterial DNA gyrase. Quercetin is a Flavonoid and to be more specific a flavonol. It is the Aglycone form of a number of other flavonoid Glycosides, such as The term flavonoid (or bioflavonoid refers to a class of Plant Secondary metabolites According to the IUPAC nomenclature they can be classified into Some foods such as garlic and apples contain high levels of quercetin. Allium sativum L, commonly known as garlic, is a species in the Onion family Alliaceae. The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. Whether this inhibits or enhances the effect of fluoroquinolones is not entirely clear. [3]

Contraindications

Medications containing metals, such as aluminium, magnesium, calcium, ferrous sulfate, iron, and zinc, are thought to form chelation complexes with fluoroquinolone antibiotics and prevent the drugs from being absorbed. WikipediaNaming Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 Atomic weight 24 Calcium (ˈkælsiəm is the Chemical element with the symbol Ca and Atomic number 20 Iron(II sulfate or ferrous sulfate is the Chemical compound with the formula ( Fe[[Sulfur S]] O 4 Iron (ˈаɪɚn is a Chemical element with the symbol Fe (ferrum and Atomic number 26 Zinc (ˈzɪŋk from Zink is a Metallic Chemical element with the symbol Zn and Atomic number 30 Because of this, avoid taking ciprofloxacin with antacids which contain aluminium, magnesium or calcium. An antacid is any substance generally a base or Basic salt, which counteracts stomach acidity. Sucralfate, which has a high aluminium content, also reduces the bioavailability of ciprofloxacin to approximately 4%. Sucralfate (brand names Sucramal in Italy Carafate in USA Sucrafil, in India Sutra in parts of South-East Asia Sulcrate [4] 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. [5]

Heavy exercise is discouraged, as achilles tendon rupture has been reported in patients taking ciprofloxacin. Achilles tendon rupture is the most common injury involving a break in a tendon Achilles tendon rupture due to ciprofloxacin use is typically associated with renal failure. Chronic kidney disease (CKD also known as chronic renal disease, is a progressive loss of renal function over a period of months or years

The toxicity of drugs that are metabolised by the cytochrome P450 system is enhanced by concomitant use of some quinolones. Cytochrome P450 (abbreviated CYP, P450, infrequently CYP450) is a very large and diverse superfamily of Hemoproteins found in all Domains They may also interact with the GABA A receptor and cause neurological symptoms; this is further augmented by certain non-steroidal anti-inflammatory drugs. The GABAA receptor is one of two ligand-gated Ion channels responsible for mediating the effects of Gamma-aminobutyric acid (GABA the major Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAID s or NAID s, are drugs with Analgesic, Antipyretic and in higher [6]

Fluoroquinolones are increasingly contraindicated for patients who have been to S. E. Asia due to the growing prevalence of antibiotic resistance to the class of antibiotics in that region. [7]

Side effects

In 2005 the FDA changed the package insert for Cipro[8] to acknowledge the tendon ruptures and the development of irreversible neurological conditions.

The incidence of side effects for ciprofloxacin is widely believed by physicians to be acceptable and relatively safe. However, the safety of Cipro has been increasingly challenged with a large number of patients suffering serious adverse effects with disabling effects lasting months or years with higher doses and/or longer duration of administration. [9] Manufacturer funded studies report that approximately 9% of patients taking the medication experience side effects ranging from mild to moderate, with the vast majority of those relating to metabolic-nutritional problems and the central nervous system. In Vertebrates the central nervous system ( CNS) is the part of the Nervous system which is enclosed in the Meninges. [10] Compared to other Fluoroquinolones the incidence and severity of side effects from ciprofloxacin is low. [11]

Dosing

Ciprofloxacin is available in oral tablets (250, 500, 750, 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 an anti-parasitic drug used against Protozoan infections

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

Cipro® brand ciprofloxacin 500mg tablets
Cipro® brand ciprofloxacin 500mg tablets

Business aspects

The discovery and development of ciprofloxacin opened up a new class of antibiotics for further research, development, and marketing.

Bayer Pharmaceutical embarked on a plan to remake itself from a pharmaceutical manufacturer into a player in the international pharmaceutical business, with a lock on the antibiotic field. For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa 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. In modern usage an antibiotic is a Chemotherapeutic agent with activity against Microorganisms such as Bacteria, fungi or Protozoa For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German Faced with the imminent expiry of its patent rights to ciprofloxacin in the early 2000s and the loss of market share to generic ciprofloxacin, Bayer has focused on the development and patenting of new variations of the existing drug (i. A patent is a set of Exclusive rights granted by a State to an inventor or his assignee for a fixed period of time in exchange for a disclosure of an For other uses see Bayer (disambiguation or Beyer or Buyer. Bayer AG (German ˈbaɪə () is a German e. pediatric ciprofloxacin, intravenous ciprofloxacin, once-a-day ciprofloxacin, etc. ), which will provide new patents and new sources of revenue as patients move to these newer versions of ciprofloxacin.

"Cipro" became a household word during the 2001 anthrax attacks. The 2001 Anthrax attacks in the United States, also known as Amerithrax from its Federal Bureau of Investigation (FBI case name occurred over

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.

References

  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. ^ Dreses-Werringloer U, Padubrin I, Jurgens-Saathoff B, Hudson AP, Zeidler H, Kohler L. Persistence of Chlamydia trachomatis Is Induced by Ciprofloxacin and Ofloxacin In Vitro. Antimicrob Agents Chemother 2000 Dec;44(12):3288-97. PMID 11083629
  3. ^ 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.
  4. ^ Spivey JM, Cummings DM, Pierson NR. Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy 1996;16:314-6. PMID 8820479.
  5. ^ Drug effects of Ciprofloxacin
  6. ^ Brouwers JR. Drug interactions with quinolone antibacterials. Drug Saf 1992;7:268-81. PMID 1524699.
  7. ^ Fluoroquinolone Resistance in Neisseria gonorrhoeae -- Colorado and Washington, 1995 [1]
  8. ^ Cipro package insert. Page 7 Warning of tendon ruptures and irreversible neurological conditions.
  9. ^ Cipro levaquin side effects floxin avelox
  10. ^ Schacht P. (1989). Safety of oral ciprofloxacin. An update based on clinical trial results. American Journal of Medicine: Nov 30;87(5A):98S-102S.
  11. ^ Rubinstein, E. (2001). History of Quinolones and Their Side Effects. Chemotherapy. 47:3-8 (DOI: 10. 1159/000057838)

External links

Dictionary

ciprofloxacin

-noun

  1. A synthetic broad-spectrum antibiotic, derived from fluoroquinolone.
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