Cas no 12650-69-0 (Mupirocin)
Mupirocin Chemical and Physical Properties
Names and Identifiers
-
- Mupirocin
- Pseudomonic acid
- 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
- Bactroban
- Bactroban Nasal
- BRL-4910A
- Centany
- Mupirocina
- Mupirocine
- Mupirocinum
- Plasimine
- Pseudomonic acid A
- 5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester
- Turixi
- Turixin
- Mupricin
- Bactoderm
- BRL 4910A
- Aids108090
- Aids-108090
- C26H44O9
- Bactroban (TN)
- Mupirocinum [Latin]
- Mupirocine [French]
- Mupirocina [Spanish]
- D0GX863OA5
- MRC
- 6-Chloro-2,4-dimethoxy pyrimidine
- 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
-
- MDL: MFCD01711620
- 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
- InChI Key: MINDHVHHQZYEEK-HBBNESRFSA-N
- SMILES: [C@]1([H])(C[C@H]2CO[C@@H](C/C(/C)=C/C(=O)OCCCCCCCCC(=O)O)[C@H](O)[C@@H]2O)O[C@@]1([H])[C@@H](C)[C@@H](O)C
Computed Properties
- Exact Mass: 500.29900
- Monoisotopic Mass: 500.299
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 9
- Heavy Atom Count: 35
- Rotatable Bond Count: 17
- Complexity: 694
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 8
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- Tautomer Count: nothing
- XLogP3: 3
- Topological Polar Surface Area: 146
Experimental Properties
- Color/Form: Crystallized from diethyl ether, melting point 77 ~ 78 ℃.
- Density: 1.1830
- Melting Point: 78°C(lit.)
- Boiling Point: 672.3°C at 760 mmHg
- Flash Point: >110°(230°F)
- Refractive Index: 1.524
- Solubility: H2O: 12?mg/mL, soluble
- Water Partition Coefficient: Soluble in DMSO or methanol. Sparingly soluble in water
- PSA: 146.05000
- LogP: 2.59250
- λmax: 222(EtOH)(lit.)
- Merck: 6302
- Specific Rotation: -15.7° - -20.0° (c=1, MeOH)
- Solubility: Soluble in DMSO or methanol. Sparingly soluble in water
Mupirocin Security Information
- Signal Word:Warning
- Hazard Statement: H317
- Warning Statement: P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
- WGK Germany:2
- Safety Instruction: S2
- Regulatory Condition Code:Class Q (sugars, alkaloids, antibiotics, hormones)
- RTECS:RA6907000
- Storage Condition:Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
Mupirocin Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| MedChemExpress | HY-B0958-10mM*1mLinDMSO |
Mupirocin |
12650-69-0 | 98.34% | 10mM*1mLinDMSO |
¥550 | 2022-03-28 | |
| MedChemExpress | HY-B0958-10mg |
Mupirocin |
12650-69-0 | 98.04% | 10mg |
¥500 | 2025-04-16 | |
| MedChemExpress | HY-B0958-50mg |
Mupirocin |
12650-69-0 | 98.04% | 50mg |
¥1400 | 2025-04-16 | |
| S e l l e c k ZHONG GUO | S4297-25mg |
Mupirocin |
12650-69-0 | 99.64% | 25mg |
¥1186.55 | 2023-09-15 | |
| S e l l e c k ZHONG GUO | S4297-100mg |
Mupirocin |
12650-69-0 | 99.64% | 100mg |
¥3914.82 | 2023-09-15 | |
| DC Chemicals | DCAPI1432-1 g |
Mupirocin |
12650-69-0 | >99% | 1g |
$500.0 | 2022-02-28 | |
| Chemenu | CM126667-50mg |
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)nonanoic acid |
12650-69-0 | 98% | 50mg |
$137 | 2021-08-05 | |
| TRC | M794000-10mg |
Mupirocin |
12650-69-0 | 10mg |
$ 68.00 | 2023-09-06 | ||
| TRC | M794000-25mg |
Mupirocin |
12650-69-0 | 25mg |
$148.00 | 2023-05-17 | ||
| TRC | M794000-50mg |
Mupirocin |
12650-69-0 | 50mg |
$ 201.00 | 2023-09-06 |
Mupirocin Suppliers
Mupirocin Related Literature
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Changgui Zhao,Ziyun Yuan,Yuanyuan Zhang,Bin Ma,Huilin Li,Shouchu Tang,Xingang Xie,Xuegong She Org. Chem. Front. 2014 1 105
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Eric J. N. Helfrich,J?rn Piel Nat. Prod. Rep. 2016 33 231
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Sian M. Cooper,Russell J. Cox,John Crosby,Matthew P. Crump,Joanne Hothersall,Wanpen Laosripaiboon,Thomas J. Simpson,Christopher M. Thomas Chem. Commun. 2005 1179
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Luoyi Wang,Zhongshu Song,Paul R. Race,James Spencer,Thomas J. Simpson,Matthew P. Crump,Christine L. Willis Chem. Sci. 2020 11 5221
-
Harald Gross,Joyce E. Loper Nat. Prod. Rep. 2009 26 1408
Additional information on Mupirocin
Mupirocin (CAS No. 12650-69-0): A Comprehensive Overview of Its Applications and Recent Research Developments
Mupirocin, a naturally occurring antibiotic with the chemical name mupirocin, is an essential compound identified by its unique CAS number 12650-69-0. This molecule has garnered significant attention in the field of pharmaceutical chemistry and microbiology due to its potent antimicrobial properties. Derived from the bacterium Staphylococcus aureus, mupirocin has been widely recognized for its efficacy against Gram-positive bacteria, making it a cornerstone in the treatment of skin infections and nasal colonization by methicillin-resistant *Staphylococcus aureus* (MRSA). The following discussion delves into the chemical properties, mechanisms of action, clinical applications, and the latest advancements in research involving mupirocin.
The chemical structure of mupirocin consists of a tricyclic lipophilic core linked to a hydrophilic amino acid side chain. This unique configuration contributes to its ability to disrupt bacterial cell wall synthesis and inhibit bacterial protein synthesis. Specifically, mupirocin interacts with isoleucyl-tRNA synthetase, an essential enzyme for bacterial protein biosynthesis, thereby preventing the elongation of the peptide chain. This mechanism ensures high specificity against Gram-positive bacteria while minimizing impact on Gram-negative organisms or human cells.
In clinical settings, mupirocin is primarily utilized in topical formulations such as ointments and creams for treating skin infections caused by susceptible bacteria. Its effectiveness in eradicating MRSA from nasal carriers has made it a critical tool in preventing hospital-acquired infections. Recent studies have highlighted its potential in combination therapies to overcome antibiotic resistance. For instance, research published in *The Journal of Antimicrobial Chemotherapy* demonstrated that combining mupirocin with other agents like daptomycin can enhance therapeutic outcomes against multidrug-resistant strains.
Moreover, the development of novel delivery systems for mupirocin has been a focal point in recent pharmaceutical research. Nanoencapsulation techniques have shown promise in improving bioavailability and prolonging the antimicrobial effect. A study published in *Advanced Drug Delivery Reviews* showcased nanocarriers based on chitosan that efficiently deliver mupirocin, reducing the required dosage and minimizing local irritation. These advancements not only enhance patient compliance but also expand the spectrum of treatable infections.
Another emerging area involves the genetic modification of bacterial strains to produce engineered versions of mupirocin with enhanced properties. Researchers at institutions such as the University of Oxford have successfully utilized CRISPR-Cas9 technology to optimize the biosynthesis pathways of *Staphylococcus aureus*, leading to higher yields of mupirocin with improved stability. Such innovations could significantly reduce production costs and increase accessibility, particularly in resource-limited settings where antibiotic resistance poses a severe public health threat.
The role of mupirocin in public health initiatives has also been underscored by global health organizations. The World Health Organization (WHO) has recommended its use as part of strategies to control MRSA outbreaks in healthcare facilities. Furthermore, ongoing clinical trials are exploring its potential in treating chronic wounds infected with drug-resistant bacteria, where traditional antibiotics have failed. These trials aim to validate mupirocin as a first-line treatment option for such challenging infections.
From a regulatory perspective, regulatory bodies such as the U.S. Food and Drug Administration (FDA) and the European Medicines Agency (EMA) have stringent guidelines for the approval and use of mupirocin formulations. These regulations ensure that patients receive safe and effective treatments while minimizing risks associated with prolonged use or misuse. Recent updates to these guidelines reflect evolving scientific understanding and emerging resistance patterns, emphasizing the need for judicious use alongside infection control measures.
In conclusion, Mupirocin (CAS No. 12650-69-0) remains a vital compound in modern medicine due to its potent antimicrobial activity and broad range of applications. Ongoing research continues to uncover new possibilities for its use, from advanced delivery systems to genetic engineering approaches that enhance its production and efficacy. As antibiotic resistance remains a pressing global challenge, compounds like mupirocin will play an increasingly critical role in safeguarding public health and improving patient outcomes worldwide.
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