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MedKoo Cat#: 574479 | Name: Mupirocin calcium dihydrate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mupirocin calcium dihydrate is an antibiotic and bacterial metabolite. 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

Mupirocin calcium dihydrate
Mupirocin calcium dihydrate
CAS#115074-43-6 (calcium)

Theoretical Analysis

MedKoo Cat#: 574479

Name: Mupirocin calcium dihydrate

CAS#: 115074-43-6 (calcium)

Chemical Formula: C52H90CaO20

Exact Mass: 1074.5651

Molecular Weight: 1075.35

Elemental Analysis: C, 58.08; H, 8.44; Ca, 3.73; O, 29.76

Price and Availability

Size Price Availability Quantity
200mg USD 750.00 2 Weeks
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Related CAS #
12650-69-0 (free acid) 73346-79-9 (lithium) 115074-43-6 (calcium)
Synonym
Mupirocin calcium salt; Calcium Mupirocin Dihydrate; Mupirocin Calcium Hydrate
IUPAC/Chemical Name
calcium 9-(((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoate dihydrate
InChi Key
DDHVILIIHBIMQU-YJGQQKNPSA-L
InChi Code
InChI=1S/2C26H44O9.Ca.2H2O/c2*1-16(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;;;/h2*13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);;2*1H2/q;;+2;;/p-2/b2*16-13+;;;/t2*17-,18-,19-,20-,21-,24+,25-,26-;;;/m00.../s1
SMILES Code
O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]2CO[C@@H](C\C(=C\C(=O)OCCCCCCCCC(=O)[O-])\C)[C@H](O)[C@@H]2O.C[C@H](O)[C@H](C)[C@@H]3O[C@H]3C[C@H]4CO[C@@H](C\C(=C\C(=O)OCCCCCCCCC(=O)[O-])\C)[C@H](O)[C@@H]4O
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
Shelf Life
>3 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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mupirocin (BRL-4910A, Pseudomonic acid) calcium hydrate is an orally active antibiotic isolated from Pseudomonas fluorescens.
In vitro activity:
Mupirocin (pseudomonic acid A), an antibiotic produced by Pseudomonas fluorescens, showed a high level of activity against staphylococci and streptococci and against certain gram-negative bacteria, including Haemophilus influenzae and Neisseria gonorrhoeae, but was much less active against most gram-negative bacilli an anaerobes. Mupirocin was highly bound (95% bound) to the protein of human serum, and activity was reduced 10- to 20-fold in the presence of human serum. Reference: Antimicrob Agents Chemother. 1985 Apr;27(4):495-8. https://pubmed.ncbi.nlm.nih.gov/3923922/
In vivo activity:
Graft infections were established in the back subcutaneous tissue of adult male Wistar rats by implantation of Dacron prostheses (1 cm(2)) followed by topical inoculation with 5 x 10(7) CFU of one staphylococcal strain. The study included a control group (no graft contamination), three contaminated groups that did not receive any antibiotic prophylaxis, three contaminated groups that received mupirocin-soaked grafts, three contaminated groups in which perioperative intraperitoneal vancomycin prophylaxis (10 mg/kg of body weight) was administered, and three contaminated groups that received mupirocin-soaked grafts and perioperative intraperitoneal vancomycin prophylaxis (10 mg/kg). Data analysis showed the efficacy of mupirocin against all three strains, with growth of the strains in treated rats significantly different than that in the untreated control. In addition, mupirocin was more effective than vancomycin against the strain with intermediate susceptibility to the glycopeptide. Reference: Antimicrob Agents Chemother. 2000 Oct;44(10):2842-4. https://pubmed.ncbi.nlm.nih.gov/10991868/
Solvent mg/mL mM
Solubility
DMSO 100.0 92.99
Ethanol 100.0 92.99
Water 6.0 5.58
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,075.35 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
Formulation protocol:
1. Mohammad H, Cushman M, Seleem MN. Antibacterial Evaluation of Synthetic Thiazole Compounds In Vitro and In Vivo in a Methicillin-Resistant Staphylococcus aureus (MRSA) Skin Infection Mouse Model. PLoS One. 2015 Nov 4;10(11):e0142321. doi: 10.1371/journal.pone.0142321. PMID: 26536129; PMCID: PMC4633232. 2. Sutherland R, Boon RJ, Griffin KE, Masters PJ, Slocombe B, White AR. Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use. Antimicrob Agents Chemother. 1985 Apr;27(4):495-8. doi: 10.1128/AAC.27.4.495. PMID: 3923922; PMCID: PMC180082. 3. Vingsbo Lundberg C, Frimodt-Møller N. Efficacy of topical and systemic antibiotic treatment of meticillin-resistant Staphylococcus aureus in a murine superficial skin wound infection model. Int J Antimicrob Agents. 2013 Sep;42(3):272-5. doi: 10.1016/j.ijantimicag.2013.05.008. Epub 2013 Jul 6. PMID: 23837927. 4. Giacometti A, Cirioni O, Ghiselli R, Goffi L, Viticchi C, Mocchegiani F, Riva A, Orlando F, Saba V, Scalise G. Mupirocin prophylaxis against methicillin-susceptible, methicillin-resistant, or vancomycin-intermediate Staphylococcus epidermidis vascular-graft infection. Antimicrob Agents Chemother. 2000 Oct;44(10):2842-4. doi: 10.1128/AAC.44.10.2842-2844.2000. PMID: 10991868; PMCID: PMC90159.
In vitro protocol:
1. Mohammad H, Cushman M, Seleem MN. Antibacterial Evaluation of Synthetic Thiazole Compounds In Vitro and In Vivo in a Methicillin-Resistant Staphylococcus aureus (MRSA) Skin Infection Mouse Model. PLoS One. 2015 Nov 4;10(11):e0142321. doi: 10.1371/journal.pone.0142321. PMID: 26536129; PMCID: PMC4633232. 2. Sutherland R, Boon RJ, Griffin KE, Masters PJ, Slocombe B, White AR. Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use. Antimicrob Agents Chemother. 1985 Apr;27(4):495-8. doi: 10.1128/AAC.27.4.495. PMID: 3923922; PMCID: PMC180082.
In vivo protocol:
1. Vingsbo Lundberg C, Frimodt-Møller N. Efficacy of topical and systemic antibiotic treatment of meticillin-resistant Staphylococcus aureus in a murine superficial skin wound infection model. Int J Antimicrob Agents. 2013 Sep;42(3):272-5. doi: 10.1016/j.ijantimicag.2013.05.008. Epub 2013 Jul 6. PMID: 23837927. 2. Giacometti A, Cirioni O, Ghiselli R, Goffi L, Viticchi C, Mocchegiani F, Riva A, Orlando F, Saba V, Scalise G. Mupirocin prophylaxis against methicillin-susceptible, methicillin-resistant, or vancomycin-intermediate Staphylococcus epidermidis vascular-graft infection. Antimicrob Agents Chemother. 2000 Oct;44(10):2842-4. doi: 10.1128/AAC.44.10.2842-2844.2000. PMID: 10991868; PMCID: PMC90159.
1: Isaacson G. Oxymetazoline, Mupirocin, Clotrimazole-Safe, Effective, Off-Label Agents for Tympanostomy Tube Care. Ear Nose Throat J. 2020 Nov;99(1_suppl):30S-34S. doi: 10.1177/0145561320912885. Epub 2020 Mar 17. PMID: 32182136. 2: 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. 3: 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. 4: 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. 5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Mupirocin. 2018 Oct 31. PMID: 30000489. 6: 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. 7: 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. 8: Lee MA, Cohen PR. Zoon Balanitis Revisited: Report of Balanitis Circumscripta Plasmacellularis Resolving With Topical Mupirocin Ointment Monotherapy. J Drugs Dermatol. 2017 Mar 1;16(3):285-287. PMID: 28301626. 9: 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. 10: 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. 11: 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. 12: Agarwal A, Nesrallah G. Long-Term Safety of Buttonhole Cannulation and Efficacy of Mupirocin Prophylaxis. Contrib Nephrol. 2015;186:64-70. doi: 10.1159/000431162. Epub 2015 Aug 5. PMID: 26283561. 13: 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. 14: 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. PMID: 24144552. 15: 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. PMID: 21336932. 16: 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. PMID: 20190824. 17: 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. PMID: 19679557. 18: Patel JB, Gorwitz RJ, Jernigan JA. Mupirocin resistance. Clin Infect Dis. 2009 Sep 15;49(6):935-41. doi: 10.1086/605495. PMID: 19673644. 19: 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. PMID: 19451132; PMCID: PMC2692503. 20: van Rijen M, Bonten M, Wenzel R, Kluytmans J. Mupirocin ointment for preventing Staphylococcus aureus infections in nasal carriers. Cochrane Database Syst Rev. 2008 Oct 8;(4):CD006216. doi: 10.1002/14651858.CD006216.pub2. PMID: 18843708.