Clarithromycin
Systematic (IUPAC) name
6-(4-dimethylamino-3-hydroxy- 6-methyl-tetrahydropyran-2-yl) oxy-14-ethyl-12,13-dihydroxy- 4-(5-hydroxy-4-methoxy-4,6- dimethyl-tetrahydropyran-2-yl) oxy-7-methoxy-3,5,7,9,11, 13-hexamethyl-1- oxacyclotetradecane-2,10-dione Image File history File links This is a lossless scalable vector image. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
Identifiers
CAS number	81103-11-9
ATC code	J01FA09
PubChem	84029
DrugBank	APRD00181
Chemical data
Formula	C38H69NO13
Mol. mass	747.953 g/mol
Pharmacokinetic data
Bioavailability	50%
Protein binding	low binding
Metabolism	hepatic
Half life	3-4 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	C (USA) B3 (Aus) CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... 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 concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... 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 nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 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) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also 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 unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... 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. ... For other uses, see Australia (disambiguation). ...
Legal status
Routes	oral

Clarithromycin is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR), skin and skin structure infections, and, in HIV and AIDS patients to prevent, and to treat, disseminated Mycobacterium avium complex (MAC). In addition, it is sometimes used to treat Legionellosis. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... 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. ... The macrolides are a group of drugs (typically antibiotics) whose activity stems from the presence of a macrolide ring, a large lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, are attached. ... Staphylococcus aureus - Antibiotics test plate. ... ÏŽ:For the noisegrind band, see Sore Throat. ... Tonsillitis is an inflammation of the tonsils in the mouth and will often, but not necessarily, cause a sore throat and fever. ... Sinusitis is an inflammation of the paranasal sinuses, which may or may not be as a result of infection, from bacterial, fungal, viral, allergic or autoimmune issues. ... Bronchitis is an inflammation of the bronchi (medium-size airways) in the lungs. ... This article is about human pneumonia. ... Binomial name Chlamydia pneumoniae Chlamydia pneumoniae is a obligate intracellular bacterium. ... Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ... For other uses, see AIDS (disambiguation). ... Mycobacterium avium complex refers to infection by two species of bacteria, Mycobacterium avium and Mycobacterium intracellulare. ... Legionellosis is an infectious disease caused by bacteria belonging to the genus Legionella. ...

Clarithromycin is available under several brand names, for example Biaxin, Klacid, Claripen and Claridar.

History

Clarithromycin was invented by scientists at the Japanese drug company Taisho Pharmaceutical in the 1970s. The product emerged through efforts to develop a version of the antibiotic erythromycin that did not experience acid instability in the digestive tract and thereby cause side effects, such as nausea and stomach ache. Taisho filed for patent protection over its new drug around 1980 and subsequently introduced a branded version of its drug, called Clarith, to the Japanese market in 1991. In 1985 Taisho had partnered with the American company Abbott Laboratories for the international rights, and Abbott also gained FDA approval for Biaxin in October 1991. The drug went generic in Europe in 2004 and in the U.S. in mid-2005. Taisho Pharmaceutical is a Japanese drug company based in Tokyo. ... Erythromycin is a macrolide antibiotic which has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins. ... Abbott Laboratories (NYSE: ABT) is a diversified pharmaceuticals and health care company. ... A generic drug (pl. ...

Potential new uses

The Australian biotechnology company Giaconda is working on a new triple drug therapy for Crohn's disease that combines clarithromycin with rifabutin and clofazimine. Giaconda is an Australian biotechnology company headquartered in Sydney. ... Crohns disease (also known as regional enteritis) is a chronic, episodic, inflammatory condition of the gastrointestinal tract characterized by transmural inflammation (affecting the entire wall of the involved bowel) and skip lesions (areas of inflammation with areas of normal lining between). ... Rifabutin is an antibiotic drug primarily used in the treatment of tuberculosis. ... Clofazimine is a fat-soluble riminophenazine dye used for the treatment of leprosy. ...

Available forms

Clarithromycin is commonly administered in tablets (Biaxin), extended-release tablets (Biaxin XL), or oral suspension. In the United States generic clarithromycin is available from Andrx, Genpharm, Ivax, Ranbaxy Laboratories, Roxane, Sandoz, Teva and Wockhardt. It is also used as part of a combination therapy to treat Helicobacter pylori. In the Middle East it is available as Claridar, produced by Dar Al Dawa. IVAX Corporation is a United States public corporation focused on manufacturing and distributing generic pharmaceutical products. ... Ranbaxy Laboratories Limited is an Indian company incorporated in 1961. ... Sandoz is the generics subsidiary of Novartis, one of the Big Pharma pharmaceutical companies. ... Teva Pharmaceutical Industries Ltd. ... Binomial name Helicobacter pylori ((Marshall 1985) Goodwin 1989) Helicobacter pylori is a helical shaped Gram-negative bacterium that colonises the mucus layer of gastric epithelium in the stomach, and also the duodenum when it has undergone gastric metaplasia. ...

Mechanism of action

Clarithromycin prevents bacteria from growing, by interfering with their protein synthesis. Clarithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translocation of peptides. Clarithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. Besides this bacteriostatic effect, clarithromycin also has bactericidal effect on certain strains such as Haemophilus influenzae, Streptococcus pneumoniae and Neisseria gonorrhoeae. Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Protein synthesis is the creation of proteins using DNA and RNA. Biological and artificial methods for creation of proteins differ significantly. ... Figure 1: Ribosome structure indicating small subunit (A) and large subunit (B). ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... Binomial name Legionella pneumophila Brenner DJ, Steigerwalt AG, McDade JE 1979 Legionella pneumophila is a thin, pleomorphic, flagellated Gram-negative bacterium of the genus Legionella. ... 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 (Klein 1884) Chester 1901 Streptococcus pneumoniae, or pneumococcus, is a Gram-positive, alpha-hemolytic diplococcus bacterium and a member of the genus Streptococcus. ... Binomial name Neisseria gonorrhoeae Zopf, 1885 Neisseria gonorrhoeae is a species of Gram-negative bacteria responsible for the disease gonorrhoea. ...

Pharmacokinetics

Unlike erythromycin, clarithromycin is acid-stable and can therefore be taken orally without being protected from gastric acids. It is readily absorbed, and diffused into most tissues and phagocytes. Due to the high concentration in phagocytes, clarithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations of clarithromycin is released. The concentration of clarithromycin in the tissues can be over 10 times higher than in plasma. Highest concentrations were found in liver and lung tissue. A phagocyte is a cell that ingests and destroys foreign matter such as microorganisms or debris via a process known as phagocytosis. ...

Metabolism

Clarithromycin has a fairly rapid first-pass hepatic metabolism, that is, it is metabolised by the liver. However, this metabolite, 14-hydroxy clarithromycin is almost twice as active as clarithromycin. The half-life of clarithromycin is about 5 hours and 14-hydroxy clarithromycin's about 7 hours. Clarithromycin's and its metabolites' main routes of elimination are urinary and biliary excretion. The liver is an organ present in vertebrates and some other animals. ...

Side effects

Most common side-effects are gastrointestinal: diarrhea, nausea, abdominal pain and vomiting, facial swelling. Less common side-effects include headaches, dizziness/motion sickness, rashes, alteration in senses of smell and taste, including a metallic taste that lasts the entire time one takes it. Dry mouth, anxiety, hallucinations, and nightmares have also been reported. In more serious cases it has been known to cause jaundice, other liver disorders, and kidney problems including kidney failure. Inform your doctor immediately if side effects are extremely bothersome or serious. Clarithromycin may cause false positives on urine drug screens for cocaine. Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... Jaundice, also known as icterus (attributive adjective: icteric), is a yellowing of the skin, conjunctiva (a clear covering over the sclera, or whites of the eyes) and mucous membranes caused by hyperbilirubinemia (increased levels of bilirubin in red blooded animals). ... Renal failure is when the kidneys fail to function properly. ...

Special precautions

Allergic reactions can occur with clarithromycin use. People with a history of allergy, asthma, hay fever or hives seem to be more susceptible to these reactions, and it is normally recommended they avoid the use of Clarithromycin. The reaction can be immediate and severe. Urticaria or hives is a skin condition, commonly caused by an allergic reaction, that is characterized by raised red skin welts. ...

Allergic symptoms include wheezing, hives, itching, swelling, spasms in the throat and breathing tubes, swelling of the face and neck, joint and muscle pain, difficulty breathing, fever and skin rashes. Rashes can range in severity, the most serious cases being toxic epidermal necrolysisand Stevens-Johnson syndrome. Nausea and vomiting are not symptoms of an allergic reaction. Toxic epidermal necrolysis is a life-threatening and usually drug-induced dermatological condition that occurs more often in women than in men. ... Stevens-Johnson syndrome (SJS) is a severe and life-threatening condition. ...

Resistance

Streptococci quickly develop resistance to clarithromycin after standard courses of treatment, most frequently via acquisition of the erm(B) gene, which confers high-level resistance to all macrolides.^[1] Streptococcus is a genus of spherical shaped Gram-positive bacteria, belonging to the phylum Firmicutes[1] and the lactic acid bacteria group. ... The macrolides are a group of drugs (typically antibiotics) whose activity stems from the presence of a macrolide ring, a large lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, are attached. ...

Contraindications

Clarithromycin should be used with caution if the patient has liver or kidney disease, certain heart problems (e.g., QT prolongation or bradycardia), or an electrolyte imbalance (e.g., low potassium or magnesium levels). Many other drugs can interact with clarithromycin, which is why the doctor should be informed of any other drugs the patient is taking concomitantly. Clarithromycin is almost never used in HIV patients due to significant interaction with HIV drugs. Schematic representation of normal ECG trace (sinus rhythm), with waves, segments, and intervals labeled. ... Bradycardia, as applied to adult medicine, is defined as a resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min. ...

References

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• Biaxin Official web site by Abbott Laboratories
• U.S. Patent 4,331,803