Mupirocin calciumProduct ingredient for Mupirocin
- Name
- Mupirocin calcium
- Drug Entry
- Mupirocin
Mupirocin, formerly termed pseudomonic acid A,1 is a novel antibacterial agent with a unique chemical structure and mode of action apart from other antibiotic agents. Produced by fermentation using the organism Pseudomonas fluorescens, mupirocin is a naturally-occurring antibiotic that displays a broad-specturm activity against many gram-positive bacteria and certain gram-negative bacteria in vitro.7 It primarily works by inhibiting bacterial protein synthesis. Due to its unique mode of action of inhibiting the activity of bacterial isoleucyl-tRNA synthetase, mupirocin does not demonstrate cross-resistance with other classes of antimicrobial agents, giving it a therapeutic advantage.7 It is available in topical formulations only due to extensive systemic metabolism1 and is used in the treatment of impetigo caused by Staphylococcus aureus and Streptococcus pyogenes and traumatic skin lesions due to secondary skin infections caused by S. aureus and S. pyogenes. There is also some clinical evidence that suggests the potential role of mupirocin in eradicating nasal carriage of Staphylococci when administered intranasally.1,3 Mupirocin is commonly marketed under the brand name Bactroban.
- Accession Number
- DBSALT001049
- Structure
Structure for Mupirocin calcium (DBSALT001049)
- Synonyms
- Mupirocin calcium / Mupirocin calcium dihydrate / Mupirocin calcium hydrate
- UNII
- RG38I2P540
- CAS Number
- 115074-43-6
- Weight
- Average: 1075.35
Monoisotopic: 1074.5651362 - Chemical Formula
- C52H90CaO20
- InChI Key
- DDHVILIIHBIMQU-YJGQQKNPSA-L
- InChI
- 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
- IUPAC Name
- calcium bis(9-{[(2E)-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]oxy}nonanoate) dihydrate
- SMILES
- O.O.[Ca++].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]1O.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]1O
- External Links
- KEGG Drug
- D02195
- ChemSpider
- 4445486
- ChEBI
- 34858
- ChEMBL
- CHEMBL3989715
- Wikipedia
- Mupirocin
- Predicted Properties
Property Value Source Water Solubility 0.00248 mg/mL ALOGPS logP 4.06 ALOGPS logP 2.45 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 4.83 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 148.88 Å2 Chemaxon Rotatable Bond Count 34 Chemaxon Refractivity 140.23 m3·mol-1 Chemaxon Polarizability 55.28 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon