Clarithromycin

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Clarithromycin
Clarithromycin structure.svg
Clarithromycin-from-xtal-3D-bs-17.png
Clinical data
Trade names Biaxin, others
Other names6-O-Methylerythromycin A
AHFS/Drugs.com Monograph
MedlinePlus a692005
License data
Pregnancy
category
  • AU:B3
Routes of
administration 		By mouth, intravenous
Drug class Macrolides
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING [1] Rx-only
  • EU:Rx-only [2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 50%
Protein binding Low binding
Metabolism Liver
Elimination half-life 3–4 h
Identifiers
  • (3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R) -4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy} -14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy -4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7 -methoxy-3,5,7,9,11,13-hexamethyl -1-oxacyclotetradecane-2,10-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.119.644 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C38H69NO13
Molar mass 747.964 g·mol−1
3D model (JSmol)
  • CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)O)(C)O
  • InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1 X mark.svgN
  • Key:AGOYDEPGAOXOCK-KCBOHYOISA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections. [3] This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. [3] Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously. [3]

Contents

Common side effects include nausea, vomiting, headaches, and diarrhea. [3] Severe allergic reactions are rare. [3] Liver problems have been reported. [3] It may cause harm if taken during pregnancy. [3] It is in the macrolide class and works by slowing down bacterial protein synthesis. [3] Clarithromycin resistance is already a major challenge to healthcare systems and such resistance is spreading, leading to recommendations to test the susceptibility of pathogenic organisms to the antibiotic before commencing clarithromycin therapy. [4]

Clarithromycin was developed in 1980 and approved for medical use in 1990. [5] [6] It is on the World Health Organization's List of Essential Medicines. [7] Clarithromycin is available as a generic medication. [3] It is made from erythromycin and is chemically known as 6-O-methylerythromycin. [8]

Medical uses

Antibiotic

Clarithromycin is primarily used to treat a number of bacterial infections including pneumonia, Helicobacter pylori , and as an alternative to penicillin in strep throat. [3] Other uses include cat scratch disease and other infections due to Bartonella, cryptosporidiosis, as a second line agent in Lyme disease and toxoplasmosis. [3] It may also be used to prevent bacterial endocarditis in those who cannot take penicillin. [3] It is effective against upper and lower respiratory tract infections, skin and soft tissue infections and helicobacter pylori infections associated with duodenal ulcers.[ citation needed ]

Spectrum of bacterial susceptibility

Aerobic Gram-positive bacteria

Aerobic Gram-negative bacteria

Helicobacter

Mycobacteria

Mycobacterium avium complex consisting of:

Other bacteria

Safety and effectiveness of clarithromycin in treating clinical infections due to the following bacteria have not been established in adequate and well-controlled clinical trials: [9]

Aerobic Gram-positive bacteria

Aerobic Gram-negative bacteria

Anaerobic Gram-positive bacteria

Anaerobic Gram-negative bacteria

Idopathic hypersomnia

Clarithromycin has been researched as a potential treatment for idiopathic hypersomnia (IH) in adults, but the evidence is limited. A 2021 Cochrane study determined that the evidence is inadequate to definitively determine the efficacy of clarithromycin in the management of idiopathic hypersomnia. [10] The American Academy of Sleep Medicine's 2021 clinical practice guidelines conditionally suggested its use, especially for those who don't respond to other therapies. [11] [12]

Contraindications

Side effects

The most common side effects are gastrointestinal: diarrhea (3%), nausea (3%), abdominal pain (3%), and vomiting (6%). It also can cause headaches, insomnia, and abnormal liver function tests. Allergic reactions include rashes and anaphylaxis. Less common side effects (<1%) include extreme irritability, hallucinations (auditory and visual), dizziness/motion sickness, and alteration in senses of smell and taste, including a metallic taste. Dry mouth, panic attacks, and nightmares have also been reported, albeit less frequently. [13]

Cardiac

In February 2018, the US Food and Drug Administration (FDA) issued a safety communication warning with respect to an increased risk for heart problems or death with the use of clarithromycin, and has recommended that alternative antibiotics be considered in those with heart disease. [14]

Clarithromycin can lead to a prolonged QT interval. In patients with long QT syndrome, cardiac disease, or patients taking other QT-prolonging medications, this can increase risk for life-threatening arrhythmias. [15]

In one trial, the use of short-term clarithromycin treatment was correlated with an increased incidence of deaths classified as sudden cardiac deaths in stable coronary heart disease patients not using statins. [16]

Liver and kidney

Clarithromycin has been known to cause jaundice, cirrhosis, and kidney problems, including kidney failure.[ citation needed ] Some case reports suspect it of causing liver disease. [17]

Central nervous system

Common adverse effects of clarithromycin in the central nervous system include dizziness, headaches. Rarely, it can cause ototoxicity, delirium and mania.[ citation needed ]

Infection

A risk of oral candidiasis and vaginal candidiasis, due to the elimination of the yeast's natural bacterial competitors by the antibiotic, has also been noted.[ citation needed ]

Pregnancy and breastfeeding

Clarithromycin should not be used in pregnant women except in situations where no alternative therapy is appropriate. [9] Clarithromycin can cause potential hazard to the fetus hence should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus. [9] For lactating mothers it is not known whether clarithromycin is excreted in human milk. [9]

Interactions

Clarithromycin inhibits a liver enzyme, CYP3A4, involved in the metabolism of many other commonly prescribed drugs. Taking clarithromycin with other medications that are metabolized by CYP3A4 may lead to unexpected increases or decreases in drug levels. [18] [19]

A few of the common interactions are listed below.

Colchicine

Clarithromycin has been observed to have a dangerous interaction with colchicine as the result of inhibition of CYP3A4 metabolism and P-glycoprotein transport. Combining these two drugs may lead to fatal colchicine toxicity, particularly in people with chronic kidney disease. [9]

Statins

Taking clarithromycin concurrently with certain statins (a class of drugs used to reduce blood serum cholesterol levels) increases the risk of side effects, such as muscle aches and muscle break down (rhabdomyolysis). [20]

Calcium channel blockers

Concurrent therapy with calcium channel blocker may increase risk of low blood pressure, kidney failure, and death, compared to pairing calcium channel blockers with azithromycin, a drug similar to clarithromycin but without CYP3A4 inhibition. [21] Administration of clarithromycin in combination with verapamil have been observed to cause low blood pressure, low heart rate, and lactic acidosis. [9]

Carbamazepine

Clarithromycin may double the level of carbamazepine in the body by reducing its clearance, which may lead to toxic symptoms of carbamazepine, such as double vision, loss of voluntary body movement, and nausea, as well as hyponatremia. [22]

HIV medications

Depending on the combination of medications, clarithromycin therapy could be contraindicated, require changing doses of some medications, or be acceptable without dose adjustments. [23] For example, clarithromycin may lead to decreased zidovudine concentrations. [24]

Pharmacology

Mechanism of action

Clarithromycin prevents bacteria from multiplying by acting as a protein synthesis inhibitor. It binds to 23S rRNA, a component of the 50S subunit of the bacterial ribosome, thus inhibiting the translation of peptides.[ citation needed ]

In addition to its antibiotic activity, clarithromycin has been found to act as a negative allosteric modulator of the GABAA receptor. [25] In relation to this action, it may have wakefulness-promoting effects in people with hypersomnia. [25]

Pharmacokinetics

Unlike erythromycin, clarithromycin is acid-stable, so can be taken orally without having to be protected from gastric acids. It is readily absorbed, and diffuses 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 are released; its concentration in the tissues can be over 10 times higher than in plasma. Highest concentrations are found in liver, lung tissue, and stool.

Metabolism

Clarithromycin has a fairly rapid first-pass metabolism in the liver. Its major metabolites include an inactive metabolite, N-desmethylclarithromycin, and an active metabolite, 14-(R)-hydroxyclarithromycin. Compared to clarithromycin, 14-(R)-hydroxyclarithromycin is less potent against mycobacterial tuberculosis and the Mycobacterium avium complex. Clarithromycin (20%-40%) and its active metabolite (10%-15%) are excreted in urine. Of all the drugs in its class, clarithromycin has the best bioavailability at 50%, which makes it amenable to oral administration. Its elimination half-life is about 3 to 4 hours with 250 mg administered every 12 h, but increased to 5 to 7 h with 500 mg administered every 8 to 12 h. With any of these dosing regimens, the steady-state concentration of this metabolite is generally attained within 3 to 4 days. [26]

History

Clarithromycin was invented by researchers at the Japanese drug company Taisho Pharmaceutical in 1980. [5] The product emerged through efforts to develop a version of the antibiotic erythromycin that did not experience acid instability in the digestive tract, causing side effects, such as nausea and stomachache. Taisho filed for patent protection for the drug around 1980 and subsequently introduced a branded version of its drug, called Clarith, to the Japanese market in 1991. In 1985, Taisho 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 US in mid-2005. [27]

Society and culture

A pack of clarithromycin tablets manufactured by Taisho Pharmaceutical Clarith-200.jpg
A pack of clarithromycin tablets manufactured by Taisho Pharmaceutical

Available forms

Clarithromycin is available as a generic medication. [3] In the United States, clarithromycin is available as immediate-release tablets, extended-release tablets, and granules for oral suspension. [3]

Brand names

Clarithromycin is available under several brand names in many different countries, including Biaxin, Crixan, Claritron, Clarihexal, Clacid, Claritt, Clacee, Clarac, Clariwin, Claripen, Clarem, Claridar, Cloff, Fromilid, Infex, Kalixocin, Karicin, Klaricid, Klaridex, Klacid, Klaram, Klabax, Klerimed, MegaKlar, Monoclar, Resclar, Rithmo, Truclar, Vikrol and Zeclar.[ citation needed ]

Manufacturers

In the UK the drug product is manufactured in generic form by a number of manufacturers including Somex Pharma, Ranbaxy, Aptil and Sandoz.

Research

Hypersomnolence

Clarithromycin has been studied in a phase 2 clinical trial in the treatment of central hypersomnolence (i.e., idiopathic hypersomnolence and narcolepsy without cataplexy). [25] There was no apparent improvement on an objective measure of vigilance, but subjective sleepiness was reduced with the drug compared to placebo. [25] It is thought to work for this use as a GABAA receptor negative allosteric modulator. [25]

Related Research Articles

<span class="mw-page-title-main">Amoxicillin</span> Beta-lactam antibiotic

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken orally, or less commonly by either Intramuscular injection or by an IV bolus injection, which is a relatively quick intravenous injection lasting from a couple seconds to a few minutes.

<span class="mw-page-title-main">Erythromycin</span> Antibiotic medication

Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used during pregnancy to prevent Group B streptococcal infection in the newborn, and to improve delayed stomach emptying. It can be given intravenously and by mouth. An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn.

<span class="mw-page-title-main">Macrolide</span> Class of natural products

Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but has since been used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Peptic ulcer disease</span> Ulcer of an area of the gastrointestinal tract

Peptic ulcer disease is a break in the inner lining of the stomach, the first part of the small intestine, or sometimes the lower esophagus. An ulcer in the stomach is called a gastric ulcer, while one in the first part of the intestines is a duodenal ulcer. The most common symptoms of a duodenal ulcer are waking at night with upper abdominal pain, and upper abdominal pain that improves with eating. With a gastric ulcer, the pain may worsen with eating. The pain is often described as a burning or dull ache. Other symptoms include belching, vomiting, weight loss, or poor appetite. About a third of older people with peptic ulcers have no symptoms. Complications may include bleeding, perforation, and blockage of the stomach. Bleeding occurs in as many as 15% of cases.

<i>Helicobacter pylori</i> Species of bacteria

Helicobacter pylori, previously known as Campylobacter pylori, is a gram-negative, flagellated, helical bacterium. Mutants can have a rod or curved rod shape, that exhibit less virulence. Its helical body is thought to have evolved to penetrate the mucous lining of the stomach, helped by its flagella, and thereby establish infection. The bacterium was first identified as the causal agent of gastric ulcers in 1983 by the Australian doctors Barry Marshall and Robin Warren. In 2005 they were awarded the Nobel Prize in Physiology or Medicine for this discovery.

<i>Helicobacter</i> Genus of bacteria

Helicobacter is a genus of gram-negative bacteria possessing a characteristic helical shape. They were initially considered to be members of the genus Campylobacter, but in 1989, Goodwin et al. published sufficient reasons to justify the new genus name Helicobacter. The genus Helicobacter contains about 35 species.

<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is a lincosamide antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Pantoprazole</span> Stomach acid suppressing medication

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<span class="mw-page-title-main">Azithromycin</span> Antibiotic

Azithromycin, sold under the brand names Zithromax and Azasite, is an antibiotic medication used for the treatment of several bacterial infections. This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or into the eye.

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<span class="mw-page-title-main">Furazolidone</span> Chemical compound

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<span class="mw-page-title-main">Rifaximin</span> Antibiotic medication

Rifaximin, is a non-absorbable, broad spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in over more than 30 countries for the treatment of a variety of gastrointestinal diseases like irritable bowel syndrome, and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription. It is marketed under the brand name Xifaxan by Salix Pharmaceuticals.

Helicobacter pylori eradication protocols is a standard name for all treatment protocols for peptic ulcers and gastritis in the presence of Helicobacter pylori infection. The primary goal of the treatment is not only temporary relief of symptoms but also total elimination of H. pylori infection. Patients with active duodenal or gastric ulcers and those with a prior ulcer history should be tested for H. pylori. Appropriate therapy should be given for eradication. Patients with MALT lymphoma should also be tested and treated for H. pylori since eradication of this infection can induce remission in many patients when the tumor is limited to the stomach. Several consensus conferences, including the Maastricht Consensus Report, recommend testing and treating several other groups of patients but there is limited evidence of benefit. This includes patients diagnosed with gastric adenocarcinoma, patients found to have atrophic gastritis or intestinal metaplasia, as well as first-degree relatives of patients with gastric adenocarcinoma since the relatives themselves are at increased risk of gastric cancer partly due to the intrafamilial transmission of H. pylori. To date, it remains controversial whether to test and treat all patients with functional dyspepsia, gastroesophageal reflux disease, or other non-GI disorders as well as asymptomatic individuals.

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Helicobacter heilmannii sensu lato refers to a group of bacterial species within the Helicobacter genus. The Helicobacter genus consists of at least 40 species of spiral-shaped flagellated, Gram-negative bacteria of which the by far most prominent and well-known species is Helicobacter pylori. H. pylori is associated with the development of gastrointestinal tract diseases such as stomach inflammation, stomach ulcers, duodenal ulcers, stomach cancers that are not lymphomas, and various subtypes of extranodal marginal zone lymphomas, e.g. those of the stomach, small intestines, large intestines, and rectum. H. pylori has also been associated with the development of bile duct cancer and has been associated with a wide range of other diseases although its role in the development of many of these other diseases requires further study.

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<span class="mw-page-title-main">Vonoprazan/amoxicillin</span> Combination medication

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References

  1. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  2. ↑ "Active substance: clarithromycin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 10 December 2020.
  3. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 "Clarithromycin". The American Society of Health-System Pharmacists. Archived from the original on 3 September 2015. Retrieved 4 September 2015.
  4. ↑ Mommersteeg MC, Nieuwenburg SA, Wolters LM, Roovers BH, van Vuuren HA, Verhaar AP, et al. (November 2023). "The use of non-invasive stool tests for verification of Helicobacter pylori eradication and clarithromycin resistance". United European Gastroenterol J. 11 (9): e894-903. doi: 10.1002/ueg2.12473 . PMC   10637120 . PMID   37854002.
  5. 1 2 Greenwood D (2008). Antimicrobial drugs : chronicle of a twentieth century medical triumph (1 ed.). Oxford: Oxford University Press. p. 239. ISBN   978-0-19-953484-5. Archived from the original on 5 March 2016.
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  7. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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  9. 1 2 3 4 5 6 7 8 9 10 11 12 "Biaxin Filmtab (clarithromycin tablets, USP) Biaxin XL Filmtab (clarithromycin extended-release tablets) Biaxin Granules (clarithromycin for oral suspension, USP)" (PDF). 2 November 2015. Archived (PDF) from the original on 24 August 2015. Retrieved 2 November 2015.
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  11. ↑ Maski K, Trotti LM, Kotagal S, Robert Auger R, Rowley JA, Hashmi SD, et al. (September 2021). "Treatment of central disorders of hypersomnolence: an American Academy of Sleep Medicine clinical practice guideline". Journal of Clinical Sleep Medicine. 17 (9): 1881–1893. doi:10.5664/jcsm.9328. PMC   8636351 . PMID   34743789. Recommendation 9: We suggest that clinicians use clarithromycin (vs no treatment) for the treatment of idiopathic hypersomnia in adults. (CONDITIONAL)
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  18. ↑ Hougaard Christensen MM, Bruun Haastrup M, Øhlenschlaeger T, Esbech P, Arnspang Pedersen S, Bach Dunvald AC, et al. (April 2020). "Interaction potential between clarithromycin and individual statins-A systematic review". Basic Clin Pharmacol Toxicol. 126 (4): 307–317. doi:10.1111/bcpt.13343. PMID   31628882.
  19. ↑ Herdegen T, Cascorbi I (December 2023). "Drug Interactions of Tetrahydrocannabinol and Cannabidiol in Cannabinoid Drugs: Recommendations for Clinical Practice". Dtsch Arztebl Int. 120 (49): 833–840. doi:10.3238/arztebl.m2023.0223. PMC  10824494. PMID   37874128. S2CID   264438050.
  20. ↑ Patel AM, Shariff S, Bailey DG, Juurlink DN, Gandhi S, Mamdani M, et al. (June 2013). "Statin toxicity from macrolide antibiotic coprescription: a population-based cohort study". Annals of Internal Medicine. 158 (12): 869–76. doi:10.7326/0003-4819-158-12-201306180-00004. PMID   23778904. S2CID   21222679.
  21. ↑ Gandhi S, Fleet JL, Bailey DG, McArthur E, Wald R, Rehman F, et al. (December 2013). "Calcium-channel blocker-clarithromycin drug interactions and acute kidney injury". JAMA. 310 (23): 2544–53. doi:10.1001/jama.2013.282426. PMID   24346990.
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  23. ↑ Sekar VJ, Spinosa-Guzman S, De Paepe E, De Pauw M, Vangeneugden T, Lefebvre E, et al. (January 2008). "Darunavir/ritonavir pharmacokinetics following coadministration with clarithromycin in healthy volunteers". Journal of Clinical Pharmacology. 48 (1): 60–5. doi:10.1177/0091270007309706. PMID   18094220. S2CID   38368595.
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