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Clarithromycin information


Clarithromycin
Clinical data
Trade namesBiaxin, others
Other names6-O-methylerythromycin A
AHFS/Drugs.comMonograph
MedlinePlusa692005
License data
  • US DailyMed: Clarithromycin
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, intravenous
Drug classMacrolides
ATC code
  • J01FA09 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING[1]Rx-only
  • EU: Rx-only[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability50%
Protein bindinglow binding
MetabolismLiver
Elimination half-life3–4 h
Identifiers
IUPAC name
  • (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
  • 81103-11-9 checkY
PubChem CID
  • 84029
DrugBank
  • DB01211 checkY
ChemSpider
  • 10342604 ☒N
UNII
  • H1250JIK0A
KEGG
  • D00276 checkY
ChEMBL
  • ChEMBL1741 ☒N
CompTox Dashboard (EPA)
  • DTXSID3022829 Edit this at Wikidata
ECHA InfoCard100.119.644 Edit this at Wikidata
Chemical and physical data
FormulaC38H69NO13
Molar mass747.964 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • 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
  • 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 ☒N
  • Key:AGOYDEPGAOXOCK-KCBOHYOISA-N ☒N
 ☒NcheckY (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]

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 was developed in 1980 and approved for medical use in 1990.[4][5] It is on the World Health Organization's List of Essential Medicines.[6] Clarithromycin is available as a generic medication.[3] It is made from erythromycin and is chemically known as 6-O-methylerythromycin.[7]

  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. ^ a b c d e f g h i "Clarithromycin". The American Society of Health-System Pharmacists. Archived from the original on 3 September 2015. Retrieved 4 September 2015.
  4. ^ 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.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 498. ISBN 978-3-527-60749-5.
  6. ^ 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.
  7. ^ Kirst HA (2012). Macrolide Antibiotics (2 ed.). Basel: Birkhäuser Basel. p. 53. ISBN 978-3-0348-8105-0. Archived from the original on 5 March 2016.

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Clarithromycin

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penicillin-resistant illnesses. Later macrolides developed, including azithromycin and clarithromycin, stemmed from chemically modifying erythromycin; these compounds were...

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and 13% are resistant to clarithromycin. At present, experts disagree on the optimal regimen. In areas of low clarithromycin resistance, including the...

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macrolides depends on the size and structure of their lactone ring. Clarithromycin and erythromycin have a 14-membered lactone ring, which is more prone...

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off-label clarithromycin, and most felt their symptoms improved with this treatment. In order to help further determine whether clarithromycin is truly...

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of vonoprazan with amoxicillin and vonoprazan with amoxicillin and clarithromycin are available. Vonoprazan is indicated for healing of all grades of...

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ATC code A02

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amoxicillin and clarithromycin A02BD05 Omeprazole, amoxicillin and clarithromycin A02BD06 Esomeprazole, amoxicillin and clarithromycin A02BD07...

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domperidone, a combination with itopride, in combination with both clarithromycin and amoxicillin, in combination with levosulpiride, and in combination...

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study, clarithromycin improved subjective sleepiness in GABA-related hypersomnia. In 2013, a retrospective review evaluating longer-term clarithromycin use...

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Erythromycin

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collected). Erythromycin was formerly also called Ilotycin. The antibiotic clarithromycin was invented by scientists at the Japanese drug company Taisho Pharmaceutical...

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symptom onset. Antibiotics used include erythromycin, azithromycin, clarithromycin, or trimethoprim/sulfamethoxazole. Evidence to support interventions...

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Peptic ulcer disease

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are treated with a combination of medications, such as amoxicillin, clarithromycin, and a PPI. Antibiotic resistance is increasing and thus treatment may...

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macrolide antibiotic clarithromycin. The company's branded version of the drug, Clarith, was launched in Japan in 1991. For clarithromycin distribution outside...

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associated with Helicobacter pylori (in combination with amoxicillin or clarithromycin ohm). Ranitidine bismuth citrate may also be effective against coronavirus...

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Gastritis

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be treated with a combination of antibiotics such as amoxicillin and clarithromycin. For those with pernicious anemia, vitamin B12 supplements are recommended...

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Helicobacter pylori

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of the main antibiotics used in eradication therapies is clarithromycin, but clarithromycin-resistant strains have become well-established and the use...

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Fixed drug reaction

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fixed drug eruptions include the following: Cetirizine Ciprofloxacin Clarithromycin Cotrimoxazole Doxycycline Fluconazole NSAIDs (e.g., ibuprofen, etoricoxib...

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Ribociclib

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inhibitors include ketoconazole and similar antifungal drugs, ritonavir, clarithromycin, as well as grapefruit. Conversely, drugs that induce CYP3A4, such as...

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Zolpidem

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CYP3A4 and CYP1A2 inhibitors such as fluvoxamine, ciprofloxacin, and clarithromycin will increase the effects of a given dose of zolpidem. Cytochrome P450...

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Leprosy

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treated with second line drugs such as fluoroquinolones, minocycline, or clarithromycin, but the treatment duration is 24 months because of their lower bactericidal...

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Cetirizine

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induce cytochrome P450 enzymes such as theophylline, erythromycin, clarithromycin, cimetidine, or alcohol. While cetirizine does not undergo extensive...

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with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States, clofazimine is considered an orphan...

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Amoxicillin

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inhibitor (such as omeprazole) and a macrolide antibiotic (such as clarithromycin); other drug combinations are also effective. Amoxicillin is effective...

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