User:Mr. Ibrahem/Mupirocin

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Mr. Ibrahem/Mupirocin
Structural formula of pseudomonic acid A (PA-A), the principal component of mupirocin
Ball-and-stick model of the pseudomonic acid A molecule, the principal component of mupirocin
Pseudomonic acid A (PA-A), the principal component of mupirocin
Clinical data
Trade namesBactroban, others
Other namesMuciprocin[1]
AHFS/Drugs.comMonograph
MedlinePlusa688004
License data
Pregnancy
category
  • AU: B1
Routes of
administration
Topical
Drug classCarboxylic acid
Legal status
Legal status
Pharmacokinetic data
Protein binding97%
Elimination half-life20 to 40 minutes
Identifiers
  • 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
Chemical and physical data
FormulaC26H44O9
Molar mass500.629 g·mol−1
3D model (JSmol)
Melting point77 to 78 °C (171 to 172 °F)
  • O=C(O)CCCCCCCCOC(=O)\C=C(/C)C[C@@H]2OC[C@H](C[C@@H]1O[C@H]1[C@@H](C)[C@@H](O)C)[C@@H](O)[C@H]2O
  • InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1 checkY
  • Key:MINDHVHHQZYEEK-HBBNESRFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis.[3][5] It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms.[3] Due to concerns of developing resistance, use for greater than ten days is not recommended.[5] It is used as a cream or ointment applied to the skin.[3]

Common side effects include itchiness and rash at the site of application, headache, and nausea.[3] Long term use may result in increased growth of fungi.[3] Use during pregnancy and breastfeeding appears to be safe.[3] Mupirocin is in the carboxylic acid class of medications.[6] It works by blocking a bacteria's ability to make protein, which usually results in bacterial death.[3]

Mupirocin was initially isolated in 1971 from Pseudomonas fluorescens.[7] It is on the World Health Organization's List of Essential Medicines.[8] The wholesale cost in the developing world is about US$2.10 for a 15 g tube.[9] In the United States, a course of treatment costs $25 to $50.[10] In 2017, it was the 186th most commonly prescribed medication in the United States, with more than three million prescriptions.[11][12]

References[edit]

  1. ^ Fleischer, Alan B. (2002). Emergency Dermatology: A Rapid Treatment Guide. McGraw Hill Professional. p. 173. ISBN 9780071379953. Archived from the original on 2017-09-10.
  2. ^ "Drug Product Database Online Query". health-products.canada.ca. Archived from the original on 30 July 2019. Retrieved 30 July 2019.
  3. ^ a b c d e f g h i "Mupirocin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  4. ^ "Single Drug Information – International Medical Products Price Guide". mshpriceguide. Archived from the original on 6 March 2021. Retrieved 16 August 2020.
  5. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 298. hdl:10665/44053. ISBN 9789241547659.
  6. ^ Khanna, Ramesh; Krediet, Raymond T. (2009). Nolph and Gokal's Textbook of Peritoneal Dialysis (3 ed.). Springer Science & Business Media. p. 421. ISBN 9780387789408. Archived from the original on 2017-09-10.
  7. ^ Heggers, John P.; Robson, Martin C.; Phillips, Linda G. (1990). Quantitative Bacteriology: Its Role in the Armamentarium of the Surgeon. CRC Press. p. 118. ISBN 9780849351297. Archived from the original on 2017-09-10.
  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. ^ "Mupirocin". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 8 December 2016.
  10. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 178. ISBN 9781284057560.
  11. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  12. ^ "Mupirocin - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 11 April 2020.