Wikipedia

User:Mr. Ibrahem/Azithromycin

< User:Mr. Ibrahem
Not to be confused with Erythromycin.


Mr. Ibrahem/Azithromycin
Clinical data
Trade namesZithromax, Azithrocin, others[1]
Other names9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A
AHFS/Drugs.comMonograph
MedlinePlusa697037
License data
Pregnancy
category
Routes of
administration		By mouth (capsule, tablet or suspension), intravenous, eye drop
Drug classMacrolide antibiotic
Legal status
Legal status
Pharmacokinetic data
Bioavailability38% for 250 mg capsules
MetabolismLiver
Elimination half-life11–14 h (single dose) 68 h (multiple dosing)
ExcretionBiliary, kidney (4.5%)
Identifiers
  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
Chemical and physical data
FormulaC38H72N2O12
Molar mass748.996 g·mol−1
3D model (JSmol)
  • CN(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]2(C)O)[C@@H]3O
  • InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1 checkY
  • Key:MQTOSJVFKKJCRP-BICOPXKESA-N checkY
  (verify)

Azithromycin is an antibiotic used for the treatment of a number of bacterial infections.[3] This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections.[3] It can also be used for a number of sexually transmitted infections, including chlamydia and gonorrhea infections.[3] Along with other medications, it may also be used for malaria.[3] It can be taken by mouth or intravenously with doses once per day.[3]

Common side effects include nausea, vomiting, diarrhea, and upset stomach.[3] An allergic reaction, such as anaphylaxis, QT prolongation, or a type of diarrhea caused by Clostridium difficile is possible.[3] No harm has been found with its use during pregnancy.[3] Its safety during breastfeeding is not confirmed, but it is likely safe.[5] Azithromycin is an azalide, a type of macrolide antibiotic.[3] It works by decreasing the production of protein, thereby stopping bacterial growth.[3]

Azithromycin was discovered 1980 by Pliva and approved for medical use in 1988.[6][7] It is on the World Health Organization's List of Essential Medicines.[8] The World Health Organization classifies it as critically important for human medicine.[9] It is available as a generic medication[10] and is sold under many trade names worldwide.[1] The wholesale cost in the developing world is about US$0.18 to US$2.98 per dose.[11] In the United States, it is about US$4 for a course of treatment as of 2018.[12] In 2017, it was the 57th most commonly prescribed medication in the United States, with more than twelve million prescriptions.[13][14]

References edit

  1. ^ a b "Azithromycin International Brands". Drugs.com. Archived from the original on 28 February 2017. Retrieved 27 February 2017.
  2. ^ a b "Azithromycin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 18 June 2020. Retrieved 24 December 2019.
  3. ^ a b c d e f g h i j k "Azithromycin". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-05. Retrieved Aug 1, 2015.
  4. ^ a b "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 18 June 2020. Retrieved 26 August 2020.
  5. ^ "Azithromycin use while Breastfeeding". Archived from the original on 5 September 2015. Retrieved 4 September 2015.
  6. ^ Greenwood, David (2008). Antimicrobial drugs : chronicle of a twentieth century medical triumph (1. publ. ed.). Oxford: Oxford University Press. p. 239. ISBN 9780199534845. Archived from the original on 2016-03-05.
  7. ^ Alapi, Erika M.; Fischer, Janos (2006). "Table of Selected Analogue Classes". In Fischer, Janos; Ganellin, C. Robin (eds.). Analogue-based Drug Discovery. Weinheim: Wiley-Vch Verlag GmbH & Co. KGaA. p. 498. ISBN 978-3-527-31257-3. Archived from the original on 17 June 2020. Retrieved 2 April 2020.
  8. ^ 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.
  9. ^ World Health Organization (2018). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528. License: CC BY-NC-SA 3.0 IGO. Archived from the original on 2 July 2020. Retrieved 28 June 2020.
  10. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. ISBN 9781284057560.
  11. ^ "Azithromycin". International Drug Price Indicator Guide. Archived from the original on 23 August 2018. Retrieved 4 September 2015.
  12. ^ "NADAC as of 2018-05-23". Centers for Medicare and Medicaid Services. Archived from the original on 24 May 2018. Retrieved 24 May 2018.
  13. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 29 March 2020.
  14. ^ "Azithromycin - Drug Usage Statistics". ClinCalc. Archived from the original on 30 March 2020. Retrieved 11 April 2020.
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