Mupirocin

Iupac Name：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

CAS No.: 12650-69-0

Molecular Weight：500.62

Modify Date.: 2023-03-09 21:20

Introduction: Mupirocin (pseudomonic acid A) is an antibiotic produced by Pseudomonasfluorescens. It is useful in the treatment of dermal infections, especially thoseinvolving S. aureus and S. epidermidis. View more+

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1. Names and Identifiers

1.1 Name: Mupirocin
1.2 Synonyms: 9-({(2E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-({(2R,3S)-3-[(2S,3S)-3-hydroxy-2-butanyl]-2-oxiranyl}methyl)tetrahydro-2H-pyran-2-yl]-3-methyl-2-butenoyl}oxy)nonanoic acid Bactoderm Bactroban Bactroban Ointment BRL 4910A L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-(2S,3S)-3-(1S,2S)-2-hydroxy-1-methylpropyloxiranylmethyl-3-methyl-, 8-carboxyoctyl ester, (2E)- L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)- L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)- (9CI) L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, [2E,8[2S,3S(1S,2S)]]- MUPIROCIN CALCIUM Mupirocin Neo-Sensitabs MUPIROCIN,USP Mupricin Pseudomonic acid Pseudomonic acid A trans-Pseudomonic acid Turixin

1.3 CAS No.: 12650-69-0

1.4 CID: 446596

1.5 EINECS(EC#): 603-145-3

1.6 Molecular Formula: C26H44O9 (isomer)

1.7 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

1.8 InChkey: MINDHVHHQZYEEK-HBBNESRFSA-N

1.9 Canonical Smiles: CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O

1.10 Isomers 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

2. Properties

2.1 Density: 1.183

2.1 Melting point: 77-780C

2.1 Boiling point: 672℃

2.1 Refractive index: 1.524

2.1 Flash Point: >110°(230°F)

2.1 Precise Quality: 500.29900

2.1 PSA: 146.05000

2.1 logP: 2.59250

2.1 Solubility: H2O: 12?mg/mL, soluble

2.2 Λmax: 222nm(EtOH)(lit.)

2.3 Appearance: solid

2.4 Storage: -20°C Freezer, Under Inert Atmosphere

2.5 Color/Form: white to tan

2.6 pKa: 4.78±0.10(Predicted)

2.7 Water Solubility: H2O: 12?mg/mL, soluble

2.8 StorageTemp: Store cool, dark and dry.

3. Use and Manufacturing

3.1 Definition: ChEBI: An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.

3.2 Produe Method: It is a kind of substance produced by the pseudomonas fluorescence, including pseudomonic acids A, B, C, D. Mupirocin is pseudomonic acid A which is the major metabolite.

3.3 Usage: 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.

4. Safety and Handling

4.1 Safety Statements: S2

4.1 WGK Germany: 2

4.1 RTECS: RA6907000

4.1 Specification

The?IUPAC name of?Mupirocin is?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. With the?CAS registry number 12650-69-0,?it is also named as Pseudomonic acid.?The product's categories are?active pharmaceutical ingredients; intermediates & fine chemicals; pharmaceuticals.?It is white crystalline solid?which is an antibiotic originally isolated from Pseudomonas fluorescens NCIMB 10586, developed by Beecham.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 3.44; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.64; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 38.7; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 282.5; (8)ACD/KOC (pH 7.4): 4.53; (9)#H bond acceptors: 9; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 20; (12)Index of Refraction: 1.524; (13)Molar Refractivity: 129.51 cm³; (14)Molar Volume: 423 cm³; (15)Polarizability: 51.34×10^-24 cm³; (16)Surface Tension: 49 dyne/cm; (17)Enthalpy of Vaporization: 113.01 kJ/mol; (18)Vapour Pressure: 5.91E-21 mmHg at 25°C; (19)Rotatable Bond Count: 17; (20)Exact Mass: 500.298533; (21)MonoIsotopic Mass: 500.298533; (22)Topological Polar Surface Area: 146; (23)Heavy Atom Count: 35.

Preparation of Mupirocin: It is?obtained by the Pseudomonas fluorescens which produces a class of substances, including Pseudomonas acid A, B, C, D. Mupirocin is one of the major metabolites Pseudomonas acid A.

Uses of Mupirocin:?is bacteriostatic at low concentrations and bactericidal at high concentrations. It is used topically and is effective against Gram-positive bacteria, including MRSA.?treatment for bacterial skin infections

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)CCCCCCCCOC(=O)\C=C(/C)C[C@@H]2OC[C@H](C[C@@H]1O[C@H]1[C@@H](C)[C@@H](O)C)[C@@H](O)[C@H]2O
2.?InChI:InChI=1/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

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	1638mg/kg (1638mg/kg)	?	United States Patent Document. Vol. #4206224,
mouse	LD50	oral	5gm/kg (5000mg/kg)	?	United States Patent Document. Vol. #4206224,
mouse	LD50	subcutaneous	4gm/kg (4000mg/kg)	?	United States Patent Document. Vol. #4206224,
rat	LD50	intravenous	1310mg/kg (1310mg/kg)	?	United States Patent Document. Vol. #4206224,
rat	LD50	oral	5gm/kg (5000mg/kg)	?	United States Patent Document. Vol. #4206224,
rat	LD50	subcutaneous	5gm/kg (5000mg/kg)	?	United States Patent Document. Vol. #4206224,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. Other Information

6.0 Merck: 14,6302

6.1 Topical antibiotics: The crude drug of Bactroban ointment produced by the well-known domestic pharmaceutical company SmithKline is mupirocin which is a new type of local topical antibiotic and a kind of metabolic substance produced in the culture solution of pseudomonas fluorescence, that is, Pseudomonas A. Mainly through reversibly combined with isoleucine transfer RNA synthetase, this product can prevent the isoleucine incorporation and terminate the protein synthesis in cells containing isoleucine, leading to bacterial death. At low concentrations, this product has the inhibitory effect and at high concentrations, it has the bactericidal effect. This product is highly sensitive to a variety of gram-positive bacteria associated with skin infections, particularly staphylococcus aureus (including drug-resistant staphylococcus aureus) and streptococcus pyogenes; and it is also available for listeria monocytogenes and erythema erysipelothrix bacteria; it is generally not sensitive to gram-negative bacteria, but have some antibacterial effect on some Gram-negative bacteria such as E. coli, neisseria, haemophilus influenzae and Neisseria gonorrhoeae and is not sensitive to the majority of anaerobic bacteria and the normal flora of the skin and has low efficacy against fungi. Rate of occurrence is very low in vitro resistant mutants. After applied into the skin, this medicine can penetrate into the stratum corneum, but the absorption rate is very low. The binding rate of this drug and human serum protein is 95%. when absorbed, it is rapidly metabolized to an inactive substance single spore acid (Monic Acid) and excreted by the kidneys. The minimum inhibitory concentration of most sensitive staphylococcus is 0.01-0.25mg/L, that of sensitive streptococcus is 0.06-0.5mg/L, and that of listeriosis is 8mg/L. This product is more effective in vitro tests under acidic conditions than that under alkaline conditions. When human serum exists, activity of this drug reduce to 1/10-1/20.

6.2 Side effects: Topical application of this drug is generally no adverse reactions, occasionally with skin burning sensation, stinging sensation, aminotransferase rising, itching, dryness and erythema. Its occurrence rate is very low(3%) with a lesser degree. The medicine is generally tolerated and without being stopped. For long-term use, this drug may result in overgrowth of non-susceptible strains; nasal agent can cause headache, taste disturbance, rhinitis, pharyngitis, and other respiratory disorders.
The above information is edited by the Chemiclbook of Bai Linlin.

6.3 Precautions: 1. Allergies of pseudomonas acid or polyethylene glycol are disabled to use; patients who suffer from moderate or severe renal impairment use it with caution; the impact on pregnant or lactating women are not clear, temporarily not available.
2. Ointments made from polyethylene glycol which is used as a substrate, is only available for a small area of skin bacterial infection, and cannot be used to extensive burns or wounds so as to prevent the renal damage due to the absorption of polyethylene glycol, as well as mucous membranes, for example, used in the eyes and noses. As with nasal staph infections, the use of ointment base should be replaced by vaseline.
3. Although mupirocin toxicity is low, we should avoid the abuse or the use of the drug for a long term in case of generating drug-resistant strains.

6.4 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.

6.5 Production Methods: It is a kind of substance produced by the pseudomonas fluorescence, including pseudomonic acids A, B, C, D. Mupirocin is pseudomonic acid A which is the major metabolite.

6.6 Chemical Properties: White Crystalline Solid

6.7 Uses: antibacterial, antimycoplasmal, isoleucyl-tRNA synthetase inhibitor

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

6.9 Uses: 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.

6.10 Uses: vasodilator

6.11 Uses: An antibiotic inhibitor of isoleucyl-tRNA synthetase

6.12 Definition: ChEBI: An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2 -pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydro ybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.

6.13 Brand name: Bactroban (GlaxoSmithKline); Centany (Johnson & Johnson).

6.14 Usage: Mupirocin is involved in inhibition of protein synthesis was reversed by isoleucine and Pseudomonic Acid was shown to inhibit IleRS (isoleucyl-tRNA synthetase) in vitro. It also demonstrates weak inhibitory action on FARSL (phenylalanyl-tRNA synthetase). Efficacy against staphylococci and streptococci including multiply resistant Staphylcoccus aureus and Staphylococcus epidermidis is reported with Pseudomonic Acid.

7. Computational chemical data

Molecular Weight: 500.62g/mol
Molecular Formula: C₂₆H₄₄O₉
Compound Is Canonicalized: True
XLogP3-AA: 3
Exact Mass: 500.29853298
Monoisotopic Mass: 500.29853298
Complexity: 694
Rotatable Bond Count: 17
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 146
Heavy Atom Count: 35
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4PAAAAAAAAAAAAAAAEgAAAAAAAAAkAAAAAAAAAAAAAAAAGgAACAAADRSggAICCAAABgCIAiDSCAAAAAAgAAAACAEAAEgBFBIAIQACUAAFwAALIQPI6OyOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

8. Question & Answer

Usage and Special precautions of Mupirocin Feb 15 2021
Mupirocin, an antibiotic, is used to treat impetigo as well as other skin infections caused by bacteria. It is not effective against fungal or viral infections.This medication is sometimes prescribed for other uses; ask your doctor or pharmacist for more information. Usage Mupirocin comes in an oin...

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