Mupirocin

Structural formula
General
Non-proprietary name	Mupirocin
other names	Pseudomonic acid A.
Molecular formula	C 26 H 44 O 9
External identifiers / databases
EC number	603-145-3
ECHA InfoCard	100.106.215
PubChem	446596
ChemSpider	393914
DrugBank	DB00410
Wikidata	Q413578
Drug information
ATC code	R01 AX06 ; D06 AX09 ;
Drug class	antibiotic
properties
Molar mass	500.63 g · mol -1
Physical state	firmly
Melting point	78-79 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	1310 mg kg −1 ( LD 50 , rat , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mupirocin is a drug from the group of antibiotics that is used to remove staphylococci from the nasal mucosa and in the local treatment of skin infections. It was discovered in the bacterium Pseudomonas fluorescens .

Clinical information

Application areas (indications)

Mupirocin is used to remove certain methicillin- sensitive or methicillin-resistant Staphylococcus aureus strains ( MSSA / MRSA ) from the nasopharynx. Streptococcal infections v. a. with Streptococcus pyogenes can be treated with it. There is also a preparation for the local treatment of skin infections such as impetigo , inflammation of the hair follicle ( folliculitis ) or infected eczema and for additional treatment for boils or carbuncles . Infections with gram-negative bacteria, anaerobes and Enterococcus species cannot be treated with mupirocin.

Dosage, type and duration of application

When used in the nose, an amount the size of a match head is introduced into both nasal atria two to three times a day and evenly distributed by squeezing the nostrils. A treatment duration of 5–7 days is recommended. Thereafter, there should be a two-day break in therapy and the success of the rehabilitation should be checked with another nasal swab on the following days. In the case of skin infections, the ointment with the active ingredient is applied thinly to the affected areas one to three times a day.

Contraindications (contraindications)

The ointments must not be used on the conjunctiva of the eyes. The dosage form for the treatment of skin infections must also not be used on the nasal mucosa. The treatment of the nasal ointment must not be given to infants, as they could absorb the ointment into the airways.

Use during pregnancy and breastfeeding

There are no data on use during pregnancy or breastfeeding, and it is also not known whether mupirocin is excreted in breast milk. Therefore, the indication must be particularly strict here.

Adverse effects (side effects)

When used on the nose, there may occasionally be intolerance reactions on the nasal mucosa and, very rarely, hypersensitivity reactions on the skin. The skin ointment often causes burning, occasionally itching, stinging, redness and dryness of the treated areas. Systemic allergic reactions have been described very rarely. Long-term use can lead to colonization with bacteria that are resistant to the active ingredient.

Pharmacological properties

Mechanism of action (pharmacodynamics)

As a metabolic product of the bacterial strain Pseudomonas fluorescens acts mupirocin by a bacterial enzyme , an RNA - synthetase inhibits (isoleucyl-tRNA synthetase). In this way, bacterial protein synthesis is inhibited (hindered). In higher concentrations it has a bactericidal effect . The effect is bacteriostatic in concentrations close to the “ Minimum Inhibitory Concentration , MIC”.

Absorption and distribution in the body (pharmacokinetics)

After oral or intravenous administration, mupirocin is rapidly converted into the inactive monic acid and is therefore only suitable for local use. When used on the mucous membrane, less than 1% of the amount is excreted as monic acid via the kidneys.

Trade names

Monopreparations

Nasal ointments

Mupirocin InfectoPharm 20 mg / g nasal ointment (D)
Turixin (D)
Bactroban (A, CH)

Dermatics:

Infectopyoderm (D)
Muporin (TH)

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 1089-1090, ISBN 978-0-911910-00-1 .
↑ Data sheet Mupirocin ≥ 94% (HPLC), solid from Sigma-Aldrich , accessed on December 13, 2012 ( PDF ).
↑ Entry on mupirocin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ AT Fuller, G. Mellows et al. a .: Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens. In: Nature Volume 234, Number 5329, December 1971, pp. 416-417. PMID 5003547 .

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 1089-1090, ISBN 978-0-911910-00-1 .

[Sigma-2] Data sheet Mupirocin ≥ 94% (HPLC), solid from Sigma-Aldrich , accessed on December 13, 2012 ( PDF ).

[ChemIDplus-3] Entry on mupirocin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[PMID5003547-4] AT Fuller, G. Mellows et al. a .: Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens. In: Nature Volume 234, Number 5329, December 1971, pp. 416-417. PMID 5003547 .