Mupirocin
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MedKoo CAT#: 318292

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

Description: Mupirocin is an antibiotic and bacterial metabolite that has been found in P. fluorescens.. It is bacteriostatic against S. aureus (MIC = 0.05 µg/ml) and active against skin wound clinical isolates of methicillin-resistant S. aureus (MRSA; MICs = 1-4 µg/ml). Mupirocin inhibits MRSA and P. aeruginosa biofilm formation in vitro.4 It inhibits bacterial cell wall isoleucyl-tRNA synthetase, slowing bacterial growth. Topical administration of Mupirocin (2% v/v) reduces the number of wound colony forming units (CFUs) in a mouse model of MRSA skin infection. Lithium mupirocin as been used to study mupirocin resistance in staphylococcus aureus and in mycoplasma susceptibility studies.


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: Dadashi M, Hajikhani B, Darban-Sarokhalil D, van Belkum A, Goudarzi M. Mupirocin resistance in Staphylococcus aureus: A systematic review and meta- analysis. J Glob Antimicrob Resist. 2020 Mar;20:238-247. doi: 10.1016/j.jgar.2019.07.032. Epub 2019 Aug 20. PMID: 31442624.

2: Tucaliuc A, Blaga AC, Galaction AI, Cascaval D. Mupirocin: applications and production. Biotechnol Lett. 2019 May;41(4-5):495-502. doi: 10.1007/s10529-019-02670-w. Epub 2019 Mar 29. PMID: 30927135.

3: Khoshnood S, Heidary M, Asadi A, Soleimani S, Motahar M, Savari M, Saki M, Abdi M. A review on mechanism of action, resistance, synergism, and clinical implications of mupirocin against Staphylococcus aureus. Biomed Pharmacother. 2019 Jan;109:1809-1818. doi: 10.1016/j.biopha.2018.10.131. Epub 2018 Nov 26. PMID: 30551435.

4: Bari O, Cohen PR. Successful Management of Zoon's Balanitis with Topical Mupirocin Ointment: A Case Report and Literature Review of Mupirocin-Responsive Balanitis Circumscripta Plasmacelluaris. Dermatol Ther (Heidelb). 2017 Jun;7(2):203-210. doi: 10.1007/s13555-017-0178-1. Epub 2017 Apr 5. Erratum in: Dermatol Ther (Heidelb). 2017 Jun;7(2):211. PMID: 28382428; PMCID: PMC5453920.

5: Tsai CC, Yang PS, Liu CL, Wu CJ, Hsu YC, Cheng SP. Comparison of topical mupirocin and gentamicin in the prevention of peritoneal dialysis-related infections: A systematic review and meta-analysis. Am J Surg. 2018 Jan;215(1):179-185. doi: 10.1016/j.amjsurg.2017.03.005. Epub 2017 Mar 15. PMID: 28341139.

6: George S, Leasure AR, Horstmanshof D. Effectiveness of Decolonization With Chlorhexidine and Mupirocin in Reducing Surgical Site Infections: A Systematic Review. Dimens Crit Care Nurs. 2016 Jul-Aug;35(4):204-22. doi: 10.1097/DCC.0000000000000192. PMID: 27258958.

7: Hetem DJ, Bootsma MC, Bonten MJ. Prevention of Surgical Site Infections: Decontamination With Mupirocin Based on Preoperative Screening for Staphylococcus aureus Carriers or Universal Decontamination? Clin Infect Dis. 2016 Mar 1;62(5):631-6. doi: 10.1093/cid/civ990. Epub 2015 Dec 9. PMID: 26658054.

8: Greywal T, Cohen PR. Pitted keratolysis: successful management with mupirocin 2% ointment monotherapy. Dermatol Online J. 2015 Aug 15;21(8):13030/qt6155v9wk. PMID: 26437161.

9: 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. PMID: 26142407.