9-({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)nonanoic acid

• ChemBase ID: 293
• Molecular Formular: C26H44O9
• Molecular Mass: 500.62216
• Monoisotopic Mass: 500.29853299
• SMILES: [C@H]1([C@H](CO[C@H]([C@@H]1O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)C[C@H]1[C@H]([C@H]([C@H](C)O)C)O1)O
• Canonical SMILES: OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C
• InChI: 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
• InChIKey: MINDHVHHQZYEEK-HBBNESRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-({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)nonanoic acid; 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}nonanoic acid
• IUPAC Traditional name: mupirocin; 9-({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)nonanoic acid
• Brand Name: Bactoderm; Bactroban; Bactroban Nasal; Centany; Turixin
• Synonyms: mupirocin; Mupirocin; Bifido Selective Supplement A; MUP Supplement; Mupirocin solution; Mupirocin Supplement; 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; BRL 4910A; Mupirocin; (2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]-oxiranyl]methyl]-3-methyl-L-talo-non-2-enonic Acid 8-Carboxyoctyl Ester; Bactoderm; Bactroban; Bactroban Ointment; Mupirocin Neo-Sensitabs; Mupricin; Pseudomonic Acid A; Turixin; trans-Pseudomonic Acid; MRC; Pseudomonic acid; Mupirocine; Bifido 选择性添加剂 A; MUP 添加剂; 莫匹罗星 溶液; 莫匹罗星添加剂

Database IDs

• CAS Number: 12650-69-0
• EC Number: 231-791-2
• MDL Number: MFCD01711620
• PubChem SID: 160963756; 24724542; 46505594
• PubChem CID: 446596
• ATC CODE: R01AX06; D06AX09
• CHEMBL: 719
• Chemspider ID: 393914
• DrugBank ID: DB00410
• KEGG ID: D01076
• Unique Ingredient Identifier: D0GX863OA5
• Wikipedia Title: Mupirocin
• Medline Plus: a688004

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.8340716
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.7011259
• LogD (pH = 7.4): -0.07094509
• Log P: 2.4513257
• Molar Refractivity: 129.3941 cm^3
• Polarizability: 51.53534 Å^3
• Polar Surface Area: 146.05 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.25
• LOG S: -4.28
• Solubility (Water): 2.65e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥10 mg/mL; Ethanol; Methanol
• Apperance: White Crystalline Solid; white to tan powder
• Melting Point: 77-78°C
• Optical Rotation: [α]/D -15.7 to -20°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: RA6907000
• German water hazard class: 1; 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Admin Routes: topical
• Half Life: 20 to 40 minutes
• Protein Bound: 97%
• Legal Status: Rx Only (US)
• Pregnancy Category: B (US)
• US Licence: Bactroban

Product Information

• Purity: ≥92% (HPLC)
• Grade: for microbiology
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C26H44O9

DETAILS

DrugBank - DB00410

• Drug Groups: approved; investigational
• Description: Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.; Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
• Indication: For the treatment of Staphylococci nasal carriers.
• Pharmacology: Mupirocin, an antibiotic produced from Pseudomonas fluorescens, is structurally unrelated to any other topical or systemic antibiotics. Mupirocin is used to treat infection caused by Staphylococcus aureus and beta-hemolytic streptococci including Streptococcus pyogenes. This antibiotic has little, if any, potential for cross-resistance with other antibiotics.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.
• Absorption: No measurable systemic absorption
• Half Life: 20 to 40 minutes
• Protein Binding: 97%
• Elimination: Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M7694

Biochem/physiol Actions
Antibiotic; inhibits isoleucyl-tRNA synthetase (IRS).

Sigma Aldrich - 89914

Components
(per vial, sufficient for 500 ml medium)Mupirocin 25 mgSterile Distilled Water 5 ml
Application
A selective supplement for the selective isolation of Bifidobacterium species by colony count technique from milk products.

Toronto Research Chemicals - M794000

Mupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

REFERENCES

• Hughes, J., et al.: J. Antibiot., 31, 330 (1978)
• Ward, A., et al.: Drugs, 32, 425 (1978)
• Casewell, M.W., et al.: J. Antimicrob. Chemother., 19, 1 (1978)