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Encyclopedia > Azithromycin
Azithromycin
Systematic (IUPAC) name
9-deoxy-9a-aza-9a-methyl-9a- homoerythromycin A
Identifiers
CAS number 83905-01-5
ATC code J01FA10
PubChem 55185
Chemical data
Formula C38H72N2O12 
Mol. mass 748.88
Pharmacokinetic data
Bioavailability 38% for 250 mg capsules
Metabolism hepatic
Half life 68 hours
Excretion biliary, renal (4.5%)
Therapeutic considerations
Pregnancy cat.

B1(AU) B(US) Image File history File links Azithromycin. ... 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. ... 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. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 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 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. ... 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. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... X-Ray of the bile duct during a laprascopic cholecystectomy A bile duct is any of a number of long tube-like structures that carry bile. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped 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. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status
Routes oral (capsule)

Azithromycin is an azalide, a subclass of macrolide antibiotics. Azithromycin (brand names Zithromax® in Italy and the United States; Vinzam® / Zitromax® in Spain; Zmax®; Sumamed®; Aztrin®, Zitrocin®, Azibiot®) is one of the world's best-selling antibiotics, and is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis. Recent studies have also indicated it to be effective against late-onset asthma, but these findings are controversial and not widely accepted as of yet. 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 1. ... azithromycin Azalides are a class of macrolide antibiotics which contain a nitrogen in the macrolide ring. ... 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. ... An antibiotic is a drug that kills or slows the growth of bacteria. ... 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. ... 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. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... Properties In chemistry and physics, an atom (Greek ἄτομος or átomos meaning indivisible) is the smallest particle still characterizing a chemical element. ... A lactone is a cyclic ester in organic chemistry. ... Otitis media is an inflammation of the middle ear: the space behind the ear drum. ... Inflamed tonsils Tonsillitis is an inflammation of the tonsils in the mouth and will often, but not necessarily, cause a sore throat and fever. ... Laryngitis is an inflammation of the larynx. ... Bronchitis is inflammation of the bronchi (medium-size airways) in the lungs. ... Pneumonia is an illness of the lungs and respiratory system in which the alveoli (microscopic air-filled sacs of the lung responsible for absorbing oxygen from the atmosphere) become inflamed and flooded with fluid. ... 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. ... Non-gonococcal urethritis (NGU) is an inflammation of the urethra which is not caused by gonorrheal infection. ...

Contents

Etymology

Azithromycin's name is derived from the azane-substituent and erythromycin. Its accurate chemical name is


(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13- [(2,6-dideoxy-3-C-methyl-3-O-methyl -α-L-ribo-hexopyranosyl)oxy]-2-ethyl- 3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl -11-[[3,4,6-trideoxy-3-(dimethylamino) -β-D-xylo-hexopyranosyl]]oxy]-1-oxa- 6-azacyclopentadecan-15-one.


History

A team of Pliva's researchers, Gabrijela Kobrehel, Gorjana Radobolja-Lazarevski and Zrinka Tamburašev led by Dr. Slobodan Đokić, discovered azithromycin in 1980. It was patented in 1981, and was later found by Pfizer's scientists while going through patent documents. In 1986 Pliva and Pfizer signed a licensing agreement which gave Pfizer exclusive rights for the sale of azithromycin in Western Europe and the United States. Pliva brought their azithromycin on the market in Central and Eastern Europe under the brand name of Sumamed in 1988, Pfizer Zithromax in 1991, and Zentiva Azitrox. Pliva d. ... Year 1980 (MCMLXXX) was a leap year starting on Tuesday (link displays the 1980 Gregorian calendar). ... Year 1981 (MCMLXXXI) was a common year starting on Thursday (link displays the 1981 Gregorian calendar). ... Pfizer, Incorporated (NYSE: PFE) (pronounced faɪzəɹ or faɪzÉ™), is the worlds largest pharmaceutical company. ... Year 1986 (MCMLXXXVI) was a common year starting on Wednesday (link displays 1986 Gregorian calendar). ... The borders of Western Europe were largely defined by the Cold War. ... Year 1988 (MCMLXXXVIII) was a leap year starting on Friday (link displays 1988 Gregorian calendar). ... Year 1991 (MCMXCI) was a common year starting on Tuesday (link will display the 1991 Gregorian calendar). ...


Available forms

Azithromycin is commonly administered in tablet or oral suspension (a one-dose version was made available in 2005). It is also available for intravenous injection. Tablets come in 250 mg and 500 mg doses. Oral suspension comes in 100 mg/teaspoon and 200 mg/teaspoon strengths. The 250 mg tablets are often dispensed in packages of six and commonly referred to as a "Z-Pak," whereas the 500 mg tablets are commonly available commercially in a pack of three tablets, or "Tri-Pak," intended as a three-day treatment. A common dose of oral azithromycin therapy consists of a "double dose" of medication on the first day of treatment and subsequent treatment for four or five additional days. With the "Z-Pak," this means two 250 mg tablets (a total of 500 mg) on the first day and one 250 mg tablet once daily for the next four days. It has been suggested that this article or section be merged into Mixture. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... An injection is a method of putting liquid into the body with a hollow needle and a syringe which is pierced through the skin long enough for the material to be forced into the body. ...


Azithromycin tablets are mottled pink, unscored, film-coated, modified-oval-shaped tablets containing azithromycin monohydrate equivalent to 250 mg or 500 mg azithromycin and the following inactive ingredients: butylated hydroxytoluene, calcium phosphate, carmine, colloidal silicon dioxide, FD&C red # 40 lake, FD&C yellow # 6 lake, hypromellose (2910, 15cP), lactose monohydrate, magnesium stearate, pregelatinized starch, sodium lauryl sulfate, talc, titanium dioxide and triacetin. The 250 mg tablets have the following appearance: they are mottled pink, of a modified-oval-shape, and have "Pfizer" engraved into one side with "306" engraved into the other. The 500 mg tablet is similar in appearance with the exception of its relative size and "ZTM500" engraved onto one side with "Pfizer" on the reverse. As with all medications, generic azithromycin tablets produced by companies other than Pfizer without the Zithromax brand name may have different appearances, but they tend to share the same general shape and coloration. Butylated hydroxytoluene (BHT) is a fat-soluble organic compound primarily used as an antioxidant food additive (E number E321). ... Calcium phosphate is the name given to a family of minerals containing calcium ions (Ca2+) together with orthophosphates (PO43-), metaphosphates or pyrophosphates (P2O74-) and occasionally hydrogen or hydroxide ions. ... Carmine Carminic acid Carmine (IPA: []), also called Crimson Lake, Cochineal, Natural Red 4, C.I. 75470 or E120, is a pigment of a bright red color obtained from the carminic acid produced by some scale insects, such as the cochineal and the Polish cochineal, and is used as a general... A colloid or colloidal dispersion, is a form of matter intermediate between a true solution and a mixture (suspension). ... R-phrases R42 R43 R49 S-phrases S22 S36 S37 S45 S53 Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... The United States Federal Food, Drug, and Cosmetic Act (FD&C) is a set of laws passed by Congress in 1938 giving authority to the Food and Drug Administration to oversee the safety of food, drugs, and cosmetics. ... Allura Red AC Allura Red AC, also called Allura Red, Food Red 17, C.I. 16035, and FD&C Red 40, is a red azo dye. ... Food coloring spreading on a thin water film. ... The United States Federal Food, Drug, and Cosmetic Act (FD&C) is a set of laws passed by Congress in 1938 giving authority to the Food and Drug Administration to oversee the safety of food, drugs, and cosmetics. ... Sunset Yellow FCF (also known as Orange Yellow S, and FD&C Yellow 6) is a colourant that may be added to foods to induce a colour change. ... Food coloring spreading on a thin water film. ... Hypromellose, short for hydroxypropyl methylcellulose (HPMC), is a semisynthetic, inert, viscoelastic polymer used as an ophthalmic lubricant found in a variety of commercial products. ... Lactose is a disaccharide that consists of β-D-galactose and β-D-glucose molecules bonded through a β1-4 glycosidic linkage. ... Magnesium stearate, also called Octadecanoic acid,magnesium salt is a white substance, solid at room temperature, chemical formula C36H70MgO4. ... Starch (CAS# 9005-25-8) is a complex carbohydrate which is insoluble in water; it is used by plants as a way to store excess glucose. ... Sodium dodecyl sulfate (SDS or NaDS) (CH3(CH2)11OSO3Na) (FW 288. ... Talc (derived from the Persian via Arabic talq) is a mineral composed of hydrated magnesium silicate with the chemical formula H2Mg3(SiO3)4 or Mg3Si4O10(OH)2. ... Titanium dioxide, also known as titanium(IV) oxide or titania, is the naturally occurring oxide of titanium, chemical formula TiO2. ... The triglyceride 1,2,3-triacetoxypropane is more generally known as triacetin and glycerin triacetate. ...


Microbiology

Azithromycin prevents bacteria from growing by interfering with their protein synthesis. Azithromycin binds to the 50S subunit of the bacterial ribosome, and thus inhibits translation of mRNA. Nucleic acid synthesis is not affected. Azithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Haemophilus influenzae. 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. ... Biological and artificial methods for creation of proteins differ significantly. ... Figure 1: Ribosome structure indicating small subunit (A) and large subunit (B). ... Translation is the second process of protein biosynthesis (part of the overall process of gene expression). ... The interaction of mRNA in a eukaryote cell. ... 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. ... Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ... 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. ...


Azithromycin has been proven to be most effective against the most isolates of the following microorganisms:

Azithromycin has been shown to be effective against malaria when used in combination with artesunate or quinine; the optimal dose for this is not yet known.[1] Binomial name Rosenbach 1884 Staphylococcus aureus , (literally Golden Cluster Seed) the most common cause of staph infections, is a spherical bacterium, frequently living on the skin or in the nose of a person, that can cause a range of illnesses from minor skin infections (such as pimples, boils, and cellulitis... Streptococcus agalactiae is a gram-positive streptococcus characterized by the presence of group B Lancefield antigen. ... Binomial name Streptococcus pneumoniae (Klein 1884) Chester 1901 Streptococcus pneumoniae is a species of Streptococcus that is a major human pathogen. ... Binomial name Streptococcus pyogenes Rosenbach 1884 Streptococcus pyogenes is a Gram-positive coccus that grows in long chains depending on the culture method. ... Binomial name Haemophilus ducreyi A chancroid is an STD characterized by painful sores on the genitalia. ... 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. ... Moraxella catarrhalis is a gram-negative, aerobic, oxidase-positive diplococcus. ... Binomial name Neisseria gonorrhoeae Zopf, 1885 Neisseria gonorrhoeae is a species of Gram-negative bacteria responsible for the disease gonorrhoea. ... Binomial name Chlamydia pneumoniae Chlamydia pneumoniae is a obligate intracellular bacterium. ... Binomial name Chlamydia trachomatis Busacca, 1935 Chlamydia trachomatis is a species of the chlamydiae, a group of obligately intracellular bacteria. ... Binomial name Mycoplasma pneumoniae Somerson et al. ... Malaria is a vector-borne infectious disease that is widespread in tropical and subtropical regions, including parts of the Americas, Asia, and Africa. ... Artemisinin is a drug used to treat multi-drug resistant strains of falciparum malaria. ... Quinine (IPA: ) is a natural white crystalline alkaloid having antipyretic (fever-reducing), antimalarial, analgesic (painkilling), and anti-inflammatory properties and a bitter taste. ...


Pharmacokinetics

Unlike erythromycin, azithromycin is acid-stable and can therefore be taken orally with no need of protection from gastric acids. It is readily absorbed, and diffused into most tissues and phagocytes. Due to the high concentration in phagocytes, azithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations of azithromycin are released. The concentration of azithromycin in the tissues can be over 50 times higher than in plasma. This is due to ion trapping and the high lipid solubility. A phagocyte is a cell that ingests and destroys foreign matter such as microorganisms or debris via a process known as phagocytosis. ...


Metabolism

Following a single 500 mg dose, plasma concentrations of azithromycin declined in a polyphasic pattern with a mean apparent plasma clearance of 630 mL/min and a terminal elimination half-life of 68 hours. The prolonged terminal half-life is thought to be due to extensive uptake and subsequent release of drug from tissues. Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... In medicine, the clearance, also renal clearance or renal plasma clearance (when referring to the function of the kidney), of a substance is the inverse of the time constant that describes its removal rate from the body divided by its volume of distribution (or total body water). ...


Biliary excretion of azithromycin, predominantly unchanged, is a major route of elimination. Over the course of a week, approximately 6% of the administered dose appears as unchanged drug in urine. Bilirubin is a yellow breakdown product of normal heme catabolism. ... This article or section is in need of attention from an expert on the subject. ...


Side effects

Most common side effects are gastrointestinal; diarrhea (4-5%), nausea (3%), abdominal pain (2-3%) and vomiting. Fewer than 1% of patients stop taking the drug due to side effects. Serious allergic reactions, dermatologic reactions, and fatalities have been reported but are extremely rare. As with all antimicrobial agents, pseudomembranous colitis can occur during and up to several weeks after azithromycin therapy. This drug may interfere with the effectiveness of birth control pills; other forms of contraception may be required during the treatment period. Pseudomembranous colitis is an infection of the colon often, but not always, caused by the bacterium Clostridium difficile. ...


Allergic reaction

Patients who suffer from an allergic reaction to Azithromycin will often experience blood in the stool 4-10 days after ingestion, although cases of this have been recorded as early as after the first day of ingestion. These allergies are usually non-severe if the treatment is immediatley stopped.


Reference links

  1. ^ Noedl H, Krudsood S, Chalermratana K, et al. (2006). "Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomised, phase 2 clinical trial in Thailand" 43 (10): 1264–71. PMID 17051490. 
  • MedicineNet.com - Azithromycin

  Results from FactBites:
 
Azithromycin - Wikipedia, the free encyclopedia (428 words)
Azithromycin is an azalide, a subclass of macrolide antibiotics.
Azithromycin is derived from erythromycin by adding a nitrogen atom into the lactone ring of erythromycin A, thus making the lactone ring 15-membered.
Azithromycin is commonly administered in tablet or oral suspension (a one-dose version was made available in 2005).
  More results at FactBites »

 
 

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