Mupirocin
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MedKoo CAT#: 318292

CAS#: 12650-69-0 (free acid)

Description: Mupirocin is an antibiotic of the monoxycarbolic acid class. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. It is used topically and is effective against Gram-positive bacteria, including MRSA. Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional hydroxyl group at C8, pseudomonic acid C with a double bond between C10 and C11, instead of the epoxide of PA-A, and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin.


Chemical Structure

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Mupirocin
CAS# 12650-69-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 318292
Name: Mupirocin
CAS#: 12650-69-0 (free acid)
Chemical Formula: C26H44O9
Exact Mass: 500.2985
Molecular Weight: 500.6222
Elemental Analysis: C, 62.38; H, 8.86; O, 28.76

Price and Availability

Size Price Availability Quantity
25.0mg USD 390.0 2 Weeks
50.0mg USD 700.0 2 Weeks
100.0mg USD 1250.0 2 Weeks
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Related CAS #: 12650-69-0 (free acid)   73346-79-9 (lithium)   115074-43-6 (calcium)    

Synonym: Mupirocin, Bactroban, Centany, BRL-4910A

IUPAC/Chemical Name: 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

InChi Key: MINDHVHHQZYEEK-HBBNESRFSA-N

InChi Code: 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

SMILES Code: O=C(O)CCCCCCCCOC(/C=C(C)/C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@H]([C@@H](O)C)C)[C@@H](O)[C@H]1O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 500.6222 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Poovelikunnel T, Gethin G, Humphreys H. Mupirocin resistance: clinical implications and potential alternatives for the eradication of MRSA. J Antimicrob Chemother. 2015 Oct;70(10):2681-92. doi: 10.1093/jac/dkv169. Epub 2015 Jul 3. Review. PubMed PMID: 26142407.

2: Hetem DJ, Bonten MJ. Clinical relevance of mupirocin resistance in Staphylococcus aureus. J Hosp Infect. 2013 Dec;85(4):249-56. doi: 10.1016/j.jhin.2013.09.006. Epub 2013 Sep 21. Review. PubMed PMID: 24144552.

3: Gurney R, Thomas CM. Mupirocin: biosynthesis, special features and applications of an antibiotic from a gram-negative bacterium. Appl Microbiol Biotechnol. 2011 Apr;90(1):11-21. doi: 10.1007/s00253-011-3128-3. Epub 2011 Feb 20. Review. PubMed PMID: 21336932.

4: Thomas CM, Hothersall J, Willis CL, Simpson TJ. Resistance to and synthesis of the antibiotic mupirocin. Nat Rev Microbiol. 2010 Apr;8(4):281-9. doi: 10.1038/nrmicro2278. Epub 2010 Mar 1. Review. PubMed PMID: 20190824.

5: Xu G, Tu W, Xu C. Mupirocin for preventing exit-site infection and peritonitis in patients undergoing peritoneal dialysis. Nephrol Dial Transplant. 2010 Feb;25(2):587-92. doi: 10.1093/ndt/gfp411. Epub 2009 Aug 13. Review. PubMed PMID: 19679557.

6: Patel JB, Gorwitz RJ, Jernigan JA. Mupirocin resistance. Clin Infect Dis. 2009 Sep 15;49(6):935-41. doi: 10.1086/605495. Review. PubMed PMID: 19673644.

7: Coates T, Bax R, Coates A. Nasal decolonization of Staphylococcus aureus with mupirocin: strengths, weaknesses and future prospects. J Antimicrob Chemother. 2009 Jul;64(1):9-15. doi: 10.1093/jac/dkp159. Epub 2009 May 18. Review. PubMed PMID: 19451132; PubMed Central PMCID: PMC2692503.

8: van Rijen MM, Bonten M, Wenzel RP, Kluytmans JA. Intranasal mupirocin for reduction of Staphylococcus aureus infections in surgical patients with nasal carriage: a systematic review. J Antimicrob Chemother. 2008 Feb;61(2):254-61. doi: 10.1093/jac/dkm480. Epub 2008 Jan 3. Review. PubMed PMID: 18174201.

9: Laupland KB, Conly JM. Treatment of Staphylococcus aureus colonization and prophylaxis for infection with topical intranasal mupirocin: an evidence-based review. Clin Infect Dis. 2003 Oct 1;37(7):933-8. Epub 2003 Sep 8. Review. PubMed PMID: 13130405.

10: Henkel T, Finlay J. Emergence of resistance during mupirocin treatment: is it a problem in clinical practice? J Chemother. 1999 Oct;11(5):331-7. Review. PubMed PMID: 10632377.

11: Mehtar S. New strategies for the use of mupirocin for the prevention of serious infection. J Hosp Infect. 1998 Sep;40 Suppl B:S39-44. Review. PubMed PMID: 9777532.

12: Cookson BD. The emergence of mupirocin resistance: a challenge to infection control and antibiotic prescribing practice. J Antimicrob Chemother. 1998 Jan;41(1):11-8. Review. PubMed PMID: 9511032.

13: Poupard JA. Update on mupirocin resistance. J Chemother. 1995 Jul;7 Suppl 3:71-4. Review. PubMed PMID: 8609541.

14: Hudson IR. The efficacy of intranasal mupirocin in the prevention of staphylococcal infections: a review of recent experience. J Hosp Infect. 1994 Jun;27(2):81-98. Review. PubMed PMID: 7930545.

15: Leyden JJ. Review of mupirocin ointment in the treatment of impetigo. Clin Pediatr (Phila). 1992 Sep;31(9):549-53. Review. PubMed PMID: 1468173.

16: Slocombe B, Perry C. The antimicrobial activity of mupirocin--an update on resistance. J Hosp Infect. 1991 Sep;19 Suppl B:19-25. Review. PubMed PMID: 1684187.

17: Pappa KA. The clinical development of mupirocin. J Am Acad Dermatol. 1990 May;22(5 Pt 1):873-9. Review. PubMed PMID: 2112164.

18: Cookson BD. Mupirocin resistance in staphylococci. J Antimicrob Chemother. 1990 Apr;25(4):497-501. Review. PubMed PMID: 2112535.

19: Mupirocin in the treatment of impetigo. Infectious Diseases and Immunization Committee, Canadian Paediatric Society. CMAJ. 1990 Mar 15;142(6):543-4. Review. PubMed PMID: 2107019; PubMed Central PMCID: PMC1451875.

20: Hill RL, Casewell MW. Nasal carriage of MRSA: the role of mupirocin and outlook for resistance. Drugs Exp Clin Res. 1990;16(8):397-402. Review. PubMed PMID: 2129029.