Mupirocin

Base Information

• Chemical Name: Mupirocin
• CAS No.: 12650-69-0
• Deprecated CAS: 62916-63-6
• Molecular Formula: C₂₆H₄₄O₉
• Molecular Weight: 500.63
• Hs Code.: 2941906000
• European Community (EC) Number: 603-145-3,658-053-6
• NSC Number: 759182
• UNII: D0GX863OA5
• DSSTox Substance ID: DTXSID0046438
• Nikkaji Number: J15.623J
• Wikipedia: Mupirocin
• Wikidata: Q413578
• NCI Thesaurus Code: C29271
• RXCUI: 42372
• Pharos Ligand ID: SQUVG7HHHVCA
• Metabolomics Workbench ID: 42771
• ChEMBL ID: CHEMBL719
• Mol file: 12650-69-0.mol

Synonyms:14C-Labeled Mupirocin;Bactroban;BRL 4910A;BRL-4910A;BRL4910A;Mupirocin;Mupirocin Calcium;Mupirocin, 14C Labeled;Mupirocin, 14C-Labeled;Mupirocin, Calcium Salt (2:1);Mupirocin, Calcium Salt (2:1), Dihydrate;Mupirocin, Lithium Salt;Mupirocin, Sodium Salt;Pseudomonic Acid;Pseudomonic Acid A

Chemical Property of Mupirocin

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 5.91E-21mmHg at 25°C
• Melting Point: 77-78 ºC
• Refractive Index: 1.524
• Boiling Point: 672.3 ºC at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 216.5 ºC
• PSA: 146.05000
• Density: 1.183 g/cm³
• LogP: 2.59250
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: 12 mg/mL, soluble
• Water Solubility.: Soluble in DMSO or methanol. Sparingly soluble in water
• XLogP3: 3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 17
• Exact Mass: 500.29853298
• Heavy Atom Count: 35
• Complexity: 694

Purity/Quality:

99%min ^*data from raw suppliers

Mupirocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O
• Isomeric SMILES: C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
• Recent ClinicalTrials: Decolonization to Reduce After-Surgery Events of Surgical Site Infection
• Recent EU Clinical Trials: Multicenter, prospective, randomized, double-blind, two-armed phase IV clinical study for efficacy and safety assessment of two 2% mupirocin containing nasal ointments (MupiroNasal 20mg/g, nasal ointment, Antibiotic-Razgrad AD, Bulgaria as test product and Bactroban 2%, nasal ointment, GlaxoSmithKline, United Kingdom as reference product), applied to the anterior nares in healthy subjects with nasal carriage of Staphylococcus aureus (S. aureus).
• Uses: Topical antibiotics. This product is generally used for the inflammation of the skin, eczema, etc., or made into mupirocin ointment in the market.By reversibly binding to isoleucine transfer RNA synthetase, this product can prevent isoleucine incorporated so that the synthesis of all proteins in cells containing isoleucine can be stopped. Mupirocin has a unique mode of action. The epoxide-containing monic acid tail of the molecule is an analog of isoleucine and, as such, is a competitive inhibitor of isoleucyltRNA synthetase in bacterial cells. The corresponding mammalian enzyme is unaffected. Mupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial. Pseudomonic acid is a potent antibiotic produced by Pseudomonas fluorescens, reported by Fuller et al. in 1971. Pseudomonic acid has broad spectrum activity against Gram positive bacteria and was approved for topical human use in 1985. Pseudomonic acid acts as a potent and selective inhibitor of isoleucyl-tRNA synthetase. vasodilator An antibiotic inhibitor of isoleucyl-tRNA synthetase
• Description: Mupirocin (pseudomonic acid A) is an antibiotic produced by Pseudomonas fluorescens. It is useful in the treatment of dermal infections, especially those involving S. aureus and S. epidermidis.
• Indications: Mupirocin (Bactroban, Centany) is a topical antibiotic produced by fermented Pseudomonas fluorescens. It has a narrow spectrum of activity, mostly against gram-positive aerobic bacteria (including Staphylococcus and methicillin-resistant Staphylococcus) and many strains of Streptococcus. It is also active against some gram-negative aerobic bacteria but is inactive against anaerobes, Chlamydia, and fungi. It has proved equal in efficacy in the treatment of impetigo when compared with oral erythromycin, with fewer adverse side effects. Mupirocin does not interfere with wound healing. It is active only on topical administration and is converted to an inert molecule on systemic administration. Prolonged use of mupirocin increases the risk of evolution of resistant organisms. Themechanism of action has not yet been fully classified, but it does differ from other available antiinfective agents, and there is little chance of cross-resistance developing. Also, unlike many other topical antibiotics, it rarely causes allergic sensitization.
• Therapeutic Function: Antibiotic
• Clinical Use: Mupirocin is mainly used as a nasal cream as part of the regimen to decolonize patients who have been found to carry methicillin-resistant Staph. aureus. It can also be applied to tracheostomy, gastrostomy and other sites that are frequently colonized with MRSA.The use of mupirocin as a means of controlling outbreaks of infection due to MRSA appears to be of only marginal benefit in an endemic situation.A Cochrane Review of nine randomized controlled trials of use of mupirocin to prevent subsequent Staph. aureus infections in nasal carriers of the organism found a statistically significant reduction in such infections at any site. A small study of local therapy to reduce the risk of peritonitis in patients on continuous ambulatory peritoneal dialysis (CAPD) found that mupirocin applied three times weekly to the dialysis catheter exit site resulted in a 92% reduction in the rate of peritonitis

Technology Process of Mupirocin

There total 23 articles about Mupirocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol (528869-25-2) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

2: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

3: 82 percent / xylene / 18 h / Heating

4: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

5: 86 percent / NaBH₄ / ethanol

6: 93 percent / imidazole / dimethylformamide

7: 94 percent / xylene / 7 h / Heating

8: 81 percent / tetrahydrofuran / -78 °C

9: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

10: 93 percent / anhydr. CuSO₄, TsOH

11: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

12: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

13: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

15: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

D-Arabinose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 17 steps

1: HBr, Ac₂O

2: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

4: 82 percent / xylene / 18 h / Heating

5: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

6: 86 percent / NaBH₄ / ethanol

7: 93 percent / imidazole / dimethylformamide

8: 94 percent / xylene / 7 h / Heating

9: 81 percent / tetrahydrofuran / -78 °C

10: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

11: 93 percent / anhydr. CuSO₄, TsOH

12: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

13: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

14: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

15: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

16: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; iodine; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

1,5-Anhydro-D-arabinitol (32742-34-0) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

2: 82 percent / xylene / 18 h / Heating

3: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

4: 86 percent / NaBH₄ / ethanol

5: 93 percent / imidazole / dimethylformamide

6: 94 percent / xylene / 7 h / Heating

7: 81 percent / tetrahydrofuran / -78 °C

8: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

9: 93 percent / anhydr. CuSO₄, TsOH

10: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

11: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

12: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

13: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

14: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; iodine; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

upstream raw materials:

Ethyl monate C

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol

(3S,4S)-3-(2-Hydroxy-ethyl)-3,4-dihydro-2H-pyran-4-ol

(3S,4S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol

Downstream raw materials:

pseudomonic acid C

Refernces

• 1、 -. "Purification of Mupirocin". Page/Page column 3. . Retrieved 2008/12/07.