Mupirocin en español

Mupirocin en español DEFAULT

Chronic therapy leads to mupirocin-resistant staphylococci.

Mupirocin is nontoxic but, when applied to denuded skin or mucous membranes, may cause itching and burning.

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Muricin® (mupirocin ointment 2%)

Muricin® (mupirocin ointment 2%)

For use in: dogs

An ointment indicated for the topical treatment of canine bacterial infections of the skin, including superficial pyoderma, caused by susceptible strains of Staphylococcus aureus and Staphylococcus intermedius.

Important safety information

As with all drugs, side effects may occur. Muricin Ointment is not for ophthalmic use. Safety in pregnant or breeding animals has not been determined. Due to a potential hazard for nephrotoxicity due to polyethylene glycol content of the product base, exercise care in use for extensive deep lesions where absorption of large quantities of polyethylene glycol is possible. Refer to the prescribing information for complete details.

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mupirocin calcium 2 % topical cream

7091Medication name

Generic name:
Mupirocin cream - topical


Brand name(s)


Mupirocin is used to treat infected cuts or wounds. It is an antibiotic. It works by stopping the growth of certain bacteria.

How to use

Read the Patient Information Leaflet if available from your pharmacist before you start using mupirocin and each time you get a refill. If you have any questions, ask your doctor or pharmacist.

Use this medication only on the skin. Clean and dry the affected area first. Then apply a small amount of cream to the area as directed by your doctor, usually 3 times a day. You may cover the treated area with a bandage.

Use this medication regularly to get the most benefit from it. Continue to use it for the full time prescribed, even if symptoms disappear after a few days. Stopping the medication too early may result in a return of the infection.

Keep mupirocin away from your eyes, nose, or mouth unless otherwise directed by your doctor. If you accidentally get it in your eyes, nose, or mouth, rinse well with plenty of water.

Tell your doctor if your condition does not get better in 3 to 5 days.

Side effects

Remember that this medication has been prescribed because your doctor has judged that the benefit to you is greater than the risk of side effects. Many people using this medication do not have serious side effects.

Although uncommon, mild burning or stinging after using this medication may occur. If you have severe burning, stinging, or irritation, stop using this medication and tell your doctor right away.

This medication may rarely cause a severe intestinal condition due to a bacteria called C. difficile. This condition may occur during treatment or weeks to months after treatment has stopped. Tell your doctor right away if you develop:

  • diarrhea that doesn't stop
  • abdominal or stomach pain/cramping
  • blood/mucus in your stool

If you have these symptoms, do not use anti-diarrhea or opioid products because they may make symptoms worse.

Use of this medication for prolonged or repeated periods may result in a new skin infection caused by fungus or yeast. Tell your doctor right away if you notice signs of a new infection, or if your current infection does not get better or if it gets worse.

A very serious allergic reaction to this drug is rare. However, get medical help right away if you notice any symptoms of a serious allergic reaction, including:

  • rash
  • itching/swelling (especially of the face/tongue/throat)
  • severe dizziness
  • trouble breathing

This is not a complete list of possible side effects. If you notice other effects not listed above, contact your doctor or pharmacist.

In the US -

Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088 or at

In Canada - Call your doctor for medical advice about side effects. You may report side effects to Health Canada at 1-866-234-2345.


Before using mupirocin, tell your doctor or pharmacist if you are allergic to it; or if you have any other allergies. This product may contain inactive ingredients, which can cause allergic reactions or other problems. Talk to your pharmacist for more details.

Before using this medication, tell your doctor or pharmacist your medical history.

Before having surgery, tell your doctor or dentist about all the products you use (including prescription drugs, nonprescription drugs, and herbal products).

During pregnancy, this medication should be used only when clearly needed. Discuss the risks and benefits with your doctor.

It is unknown if this drug passes into breast milk. Consult your doctor before breast-feeding.

Drug interactions

Drug interactions may change how your medications work or increase your risk for serious side effects. This document does not contain all possible drug interactions. Keep a list of all the products you use (including prescription/nonprescription drugs and herbal products) and share it with your doctor and pharmacist. Do not start, stop, or change the dosage of any medicines without your doctor's approval.


This medicine may be harmful if swallowed. If someone has overdosed and has serious symptoms such as passing out or trouble breathing, call 911. Otherwise, call a poison control center right away. US residents can call their local poison control center at 1-800-222-1222. Canada residents can call a provincial poison control center.


Do not share this medication with others.

This medication has been prescribed for your current condition only. Do not use it later for another infection unless your doctor tells you to.

Missed dose

If you miss a dose, use it as soon as you remember. If it is near the time of the next dose, skip the missed dose. Use your next dose at the regular time. Do not double the dose to catch up.


Store at or below 77 degrees F (25 degrees C). Do not freeze. Keep all medications away from children and pets.

Do not flush medications down the toilet or pour them into a drain unless instructed to do so. Properly discard this product when it is expired or no longer needed. Consult your pharmacist or local waste disposal company.

Important note

HOW TO USE THIS INFORMATION: This is a summary and does NOT have all possible information about this product. This information does not assure that this product is safe, effective, or appropriate for you. This information is not individual medical advice and does not substitute for the advice of your health care professional. Always ask your health care professional for complete information about this product and your specific health needs.

Information last revised August 2021.

Copyright(c) 2021 First Databank, Inc.

Selected from NATIONAL DRUG DATA FILE (NDDF) data included with permission and copyrighted by First Databank, Inc., 2019. This copyrighted material has been downloaded from a licensed data provider.

The above information is intended to supplement, not substitute for, the expertise and judgment of your health care professional. You should consult your health care professional before taking any drug, changing your diet, or commencing or discontinuing any course of treatment.

What is mupirocin ointment 2% used for


pronounced as (myoo peer' oh sin)

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.

Mupirocin comes in an ointment that is applied to the skin. Mupirocin usually is applied three times a day for 1 to 2 weeks. Follow the directions on your prescription label carefully, and ask your doctor or pharmacist to explain any part you do not understand. Use mupirocin exactly as directed. Do not use more or less of it or use it more often than prescribed by your doctor.

Wash the affected skin area thoroughly, and then gently apply a small amount (a thin film) of the ointment. You may cover the area with a sterile gauze dressing.

Do not apply mupirocin to your eyes.

Do not apply mupirocin to burns unless told to do so by your doctor.

Before using mupirocin,

  • tell your doctor and pharmacist if you are allergic to mupirocin or any other drugs.
  • tell your doctor and pharmacist what prescription and nonprescription medications you are taking, especially chloramphenicol (Chloromycetin).
  • tell your doctor if you are pregnant, plan to become pregnant, or are breast-feeding. If you become pregnant while using mupirocin, call your doctor.

Apply the missed dose as soon as you remember it. However, if it is almost time for the next dose, skip the missed dose and continue your regular dosing schedule. Do not apply a double dose to make up for a missed one.

Keep this medication in the container it came in, tightly closed, and out of reach of children. Store it at room temperature and away from excess heat and moisture (not in the bathroom).

It is important to keep all medication out of sight and reach of children as many containers (such as weekly pill minders and those for eye drops, creams, patches, and inhalers) are not child-resistant and young children can open them easily. To protect young children from poisoning, always lock safety caps and immediately place the medication in a safe location – one that is up and away and out of their sight and reach.

Unneeded medications should be disposed of in special ways to ensure that pets, children, and other people cannot consume them. However, you should not flush this medication down the toilet. Instead, the best way to dispose of your medication is through a medicine take-back program. Talk to your pharmacist or contact your local garbage/recycling department to learn about take-back programs in your community. See the FDA's Safe Disposal of Medicines website ( for more information if you do not have access to a take-back program.

Keep all appointments with your doctor. Mupirocin is for external use only. Do not let mupirocin ointment get into your eyes, nose, or mouth, and do not swallow it. Do not apply dressings, bandages, cosmetics, lotions, or other skin medications to the area being treated unless your doctor tells you.

Do not let anyone else use your medication. Ask your pharmacist any questions you have about refilling your prescription.

If you still have symptoms of infection after you finish the mupirocin, call your doctor.

It is important for you to keep a written list of all of the prescription and nonprescription (over-the-counter) medicines you are taking, as well as any products such as vitamins, minerals, or other dietary supplements. You should bring this list with you each time you visit a doctor or if you are admitted to a hospital. It is also important information to carry with you in case of emergencies.

  • Bactroban®
  • Bactroban® Nasal
  • Centany® Nasal
Last Revised - 12/15/2017

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Español mupirocin en

Dictionary English-Spanish

Mupirocin ointmentappears effective [...]

in reducing the risk of catheter-related bacteraemia.

El ungüento de mupirocina parece [...]

efectivo para reducir el riesgo de bacteriemia relacionada con el catéter.

The review of 10 studies (786

[...] patients) found thatmupirocin ointmentreduced the risk [...]

of patients developing catheter-related


bacteraemia (bacteria in the blood).

La revisión de diez estudios (786

[...] pacientes) halló que el ungüento de mupirocina redujo [...]

el riesgo de los pacientes de desarrollar


bacteriemia (bacterias en la sangre) relacionada con el catéter.

Mupirocin ointmentreduced the risk [...]

of catheter-related bacteraemia (RR 0.17, 95%CI 0.07 to 0.43) and had a significant


effect on catheter-related infections caused by S. aureus.

El ungüento de mupirocina redujo [...]

el riesgo de la bacteriemia relacionada con el catéter (CR 0,17; IC del 95%: 0,07 a 0,43)


y tuvo un efecto significativo sobre las infecciones relacionadas con el catéter causadas por S. aureus.

Of these, 917 were put in a controlled trial, with half receiving no treatment

[...] aimed at staph and half getting two antibiotic treatments,mupirocinnasalointmentand chlorhexidine soap.

De ellas, pusieron a 917 en un ensayo controlado, de los


cuales la mitad no

[...] recibió tratamiento para el estafilococo y la otra mitad recibió dos tratamientos con ungüento nasal de mupirocina [...]

y jabón de clorhexidina.

Mortality related to infection was

[...] not reduced bymupirocin,polysporin or povidone-iodineointment.

La mortalidad relacionada con la infección no fue reducida por

[...] la mupirocina, la polisporina ni el ungüento de povidona yodada.

Carefully wash the eye. Apply a thick layer

[...] of bacitracin,mupirocin,or other antibacterialointmenton the eyelid.

Lave el ojo cuidadosamente y aplique una capa gruesa de

[...] bacitracina, mupirocina u otro ungüento antibacteriano en el párpado.


[...] analysis suggestedmupirocin(RR 0.12, 95%CI 0.01 to 2.13) and povidone-iodineointment(RR 0.84, 95%CI [...]

0.24 to 2.98) had


no effect on all-cause mortality while polysporin ointment showed a significant reduction (RR 0.22, 95%CI 0.07 to 0.74).

El análisis de subgrupos indicó que la

[...] mupirocina (CR 0,12; IC del 95%: 0,01 a 2,13) y el ungüento de povidona yodada (CR 0,84; IC del 95%: 0,24 [...]

a 2,98) no tuvieron


efecto sobre la mortalidad por todas las causas mientras que el ungüento de polisporina mostró una reducción significativa (CR 0,22; IC del 95%: 0,07 a 0,74).

Antibioticointment(brand names: Neosporin, Bactroban) that contain ingredients such as bacitracin ormupirocin

Ungüentos antibióticos(nombres de marca: Neosporin, Bactrobanz) que contienen ingredientes tales como bacitracina [...]

o mupirocina.

Insufficient reporting onmupirocinresistance was [...]

noted and needs to be considered in future studies.

Se observó un informe

[...] insuficiente sobre la resistenciaa la [...]

mupirocina por lo que necesita considerarse en los estudios futuros.

Your doctor

[...] may prescribe anointmentthatincludesmupirocinto treat your MRSA.

El médico le

[...] puede recetar un ungüento que incluye mupirocina (un nombrede marca: [...]


para tratar su infección por SARM.

Antibioticointment,such as bacitracin, polysporin, ormupirocin

Ungüento antibiótico (como bacitracina, polisporina o mupirocina)

This review

[...] demonstrates that nasalmupirocinreduces exit-site/tunnel [...]

infection but not peritonitis.

Esta revisión demuestra que

[...] la mupirocina nasal reduce la infección [...]

del sitio de salida/túnel pero no la peritonitis.

Fusidic acid andmupirocinare of similar [...]


El ácido fusídico y la mupirocina tienen una [...]

eficacia similar.


[...] monitoring ofmupirocinresistance needs [...]

to be considered in future studies.

Sin embargo,

[...] la vigilancia de la resistenciaa la [...]

mupirocina debe considerarse en los estudios futuros.

This review

[...] found that nasalmupirocinreduces exit-site/tunnel [...]

infection but not peritonitis while preoperative intravenous


antibiotic prophylaxis reduces early peritonitis but not exit-site/tunnel infection.

Esta revisión estableció

[...] que la mupirocina nasal reduce la infección [...]

del sitio de salida/túnel pero no la peritonitis, al


tiempo que la profilaxis antibiótica intravenosa preoperatoria reduce la peritonitis temprana pero no la infección del sitio de salida/túnel.

Several strategies can be used to prevent these infections


occurring including the application of

[...] different types ofointments (mupirocin,povidone-iodine and [...]

polysporin) or medicinal honey


to the catheter site, and the use of different dressings which cover the catheter site (transparent or gauze and tape).

Pueden utilizarse varias estrategias para prevenir la aparición de estas


infecciones incluida la aplicación de

[...] diferentes tipos de ungüentos (mupirocina, povidona yodada [...]

y polisporina) o miel medicinal


en el sitio del catéter, y el uso de diferentes apósitos que cubren el sitio del catéter (transparentes o de gasa y cinta).

Treatment may include antibiotics applied to the skin(mupirocin)or taken by mouth (dicloxacillin), or antifungal medications to control the infection.

El tratamiento puede abarcar antibióticos tópicos (mupirocina), antibióticos orales (dicloxacilina) o medicamentos antimicóticos para controlar la infección.

Mupirocincan be applied directly to the skin (topical). It can be used along [...]

with other antibiotics, but should not be the only treatment.

La mupirocina se puede aplicar directamente sobre la piel (tópica) y se puede emplear [...]

junto con otros antibióticos, pero


no debe ser el único tratamiento.

Nasalmupirocincompared with placebo significantly [...]

reduced the exit-site and tunnel infection rate (one trial, 2716 patient


months, RR 0.58, 95% CI 0.40 to 0.85) but not peritonitis rate (one trial, 2716 patient months, RR 0.84, 95% CI 0.44 to 1.60).

La mupirocina nasal comparada con el placebo redujo [...]

significativamente la tasa de infección del sitio de salida y del túnel


(un ensayo, 2716 paciente-meses, RR 0,58; IC del 95%: 0,40 a 0,85) pero no redujo la tasa de peritonitis (un ensayo, 2716 paciente-meses, RR 0,84; IC del 95%: 0,44 a 1,60).

Prescription topical antibiotic (egmupirocin,retapamulin )

Antibióticos tópicos recetados (p. ej., mupirocina , retapamulina )

If carried out, MRSA isolates

[...] shall be tested for antimicrobial susceptibility using micro-dilution at least to the following antimicrobial agents: ciprofloxacin, erythromycin, fusidic acid, gentamicin, linezolide,mupirocin,sulphametoxazole, trimethoprim, tetracycline, chloramphenicol, vancomycin and quinupristin/dalfopristin.

En caso de que se realice, se utilizará una microdilución, al menos para los agentes antimicrobianos siguientes: Ciprofloxacino, eritromicina, ácido fusídico, gentamicina, linezolida, mupirocina, sulfametoxazol, trimetropim, tetraciclina, cloranfenicol, vancomicina y quinupristina/dalfopristina.

Topical antibiotics showed better cure rates than placebo (pooled odds ratio (OR) 6.49, 95% confidence interval (CI) 3.93


to 10.73), and no topical antibiotic was

[...] superior (pooled OR ofmupirocinversus fusidic [...]

acid 1.76, 95% CI 0.69 to 2.16).

Los antibióticos tópicos mostraron mejores tasas de curación que el placebo (odds-ratio (OR) combinado: 6,49; intervalo de confianza (IC) del 95%: 3,93 a 10,73) y


ningún antibiótico tópico fue superior (OR

[...] combinado de la mupirocina versus ácido fusídico [...]

1,76; IC del 95%: 0,69 a 2,16).

Apply antibacterialointmentand a clean bandage [...]

that will not stick to the wound.

Aplique un ungüento antibacteriano y [...]

un vendaje limpio que no se pegue a la herida.

Eye care, which may include eye

[...] drops during the day,ointmentat bedtime, or a moisture [...]

chamber at night, helps to protect


the cornea from scratching, which is crucial to the management of Bell's palsy.

El cuidado de los ojos, que puede incluir

[...] gotas durante el día, ungüento a la hora de acostarse [...]

o una cámara de humedad durante


la noche, ayuda a proteger la córnea de rasguños, lo cual es fundamental en el tratamiento de la parálisis de Bell.

Further good quality research is required before definitive conclusions can be made about the effectiveness of systemic antibiotics and topical preparations such as povidone iodine, peroxide-based preparations, ethacridine lactate,mupirocinand chlorhexidine in healing venous leg ulceration.

Se necesita más investigación de buena calidad antes de poder sacar conclusiones definitivas sobre la efectividad de los antibióticos sistémicos y las preparaciones tópicas como el yodo de povidona, las preparaciones en base a peróxido, el lactato de etacridina y la mupirocina en la curación de las úlceras venosas de la pierna.

The nasal antibiotic prophylacticmupirocinreduces exit-site/tunnel infection and preoperative intravenous antibiotic prophylaxis reduces [...]

early peritonitis in peritoneal dialysis

El antibiótico

[...] profiláctico nasal mupirocina reduce la infección del sitio de salida/túnel y la profilaxis antibiótica intravenosa preoperatoria reducela peritonitis [...]

temprana en la diálisis peritoneal.

Mupirocina, cuándo y cómo debemos aplicarla - #TuFarmacéuticoInforma


Not to be confused with Miprocin.

Structural formula of pseudomonic acid A (PA-A), the principal component of mupirocin
Ball-and-stick model of the pseudomonic acid A molecule, the principal component of mupirocin

Pseudomonic acid A (PA-A), the principal component of mupirocin

Trade namesBactroban, others
Other namesmuciprocin[1]
License data
Routes of
ATC code
Legal status
  • AU: S4 (Prescription only)
  • CA: OTC[2]
  • UK: POM (Prescription only)
  • US: ℞-only
Protein binding97%
Elimination half-life20 to 40 minutes

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 Number
CompTox Dashboard(EPA)
ECHA InfoCard100.106.215Edit this at Wikidata
Molar mass500.629 g·mol−1
3D model (JSmol)
Melting point77 to 78 °C (171 to 172 °F)


  • 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 checkY
 ☒NcheckY (what is this?)  (verify)

Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis.[3][4][5] It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms.[4] Due to concerns of developing resistance, use for greater than ten days is not recommended.[5] It is used as a cream or ointment applied to the skin.[4]

Common side effects include itchiness and rash at the site of application, headache, and nausea.[4] Long term use may result in increased growth of fungi.[4] Use during pregnancy and breastfeeding appears to be safe.[4] Mupirocin is in the carboxylic acid class of medications.[6] It works by blocking a bacteria's ability to make protein, which usually results in bacterial death.[4]

Mupirocin was initially isolated in 1971 from Pseudomonas fluorescens.[7] It is on the World Health Organization's List of Essential Medicines.[8] In 2018, it was the 165th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[9][10]

Medical uses[edit]

Mupirocin is used as a topical treatment for bacterial skin infections, for example, furuncle, impetigo, open wounds, which are typically due to infection by Staphylococcus aureus or Streptococcus pyogenes. It is also useful in the treatment of superficial methicillin-resistant Staphylococcus aureus (MRSA) infections.[11] Mupirocin is inactive for most anaerobic bacteria, mycobacteria, mycoplasma, chlamydia, yeast and fungi.[12]

Intranasal mupirocin before surgery is effective for prevention of post-operative wound infection with Staphylcoccus aureus and preventative intranasal or catheter-site treatment is effective for reducing the risk of catheter site infection in persons treated with chronic peritoneal dialysis.[13]


Shortly after the clinical use of mupirocin began, strains of Staphylococcus aureus that were resistant to mupirocin emerged, with nares clearance rates of less than 30% success.[14][15] Two distinct populations of mupirocin-resistant S. aureus were isolated. One strain possessed low-level resistance, MuL, (MIC = 8–256 mg/L) and another possessed high-level resistance, MuH, (MIC > 256 mg/L).[14] Resistance in the MuL strains is probably due to mutations in the organism's wild-typeisoleucyl-tRNA synthetase. In E. coli IleRS, a single amino acid mutation was shown to alter mupirocin resistance.[16] MuH is linked to the acquisition of a separate Ile synthetase gene, MupA.[17] Mupirocin is not a viable antibiotic against MuH strains. Other antibiotic agents, such as azelaic acid, nitrofurazone, silver sulfadiazine, and ramoplanin have been shown to be effective against MuH strains.[14]

Most strains of Cutibacterium acnes, a causative agent in the skin disease acne vulgaris, are naturally resistant to mupirocin.[18]

The mechanism of action of mupirocin differs from other clinical antibiotics, rendering cross-resistance to other antibiotics unlikely.[14] However, the MupA gene may co-transfer with other antibacterial resistance genes. This has been observed already with resistance genes for triclosan, tetracycline, and trimethoprim.[14] It may also result in overgrowth of non-susceptible organisms.

Mechanism of action[edit]

Pseudomonic acid inhibits isoleucine tRNA synthetase in bacteria,[11] leading to depletion of isoleucyl-tRNA and accumulation of the corresponding uncharged tRNA. Depletion of isoleucyl-tRNA results in inhibition of protein synthesis. The uncharged form of the tRNA binds to the aminoacyl-tRNA binding site of ribosomes, triggering the formation of (p)ppGpp, which in turn inhibits RNA synthesis.[19] The combined inhibition of protein synthesis and RNA synthesis results in bacteriostasis. This mechanism of action is shared with furanomycin, an analog of isoleucine.[20]


Figure 1. The domain structure of MmpA, MmpC, and MmpD for the synthesis of monic acid. The biosynthesis of monic acid is not colinear but has been rearranged in this diagram. The protein name is displayed inside of the arrow with module and domain structure listed below. ACP=acyl carrier protein, AT=acyl transferase, DH=dehydratase, ER=enoyl reductase, HMG=3-hydroxy-3-methylglutaric acid, MeT=methyl transferase, KR=ketoreductase, KS=ketosynthase, TE=thioesterase.
Figure 2. The structure of pseudomonic acid A–D, labeled A to D, respectively.
Figure 4. The pyranring of mupirocin is generated in this proposed multistep reaction. Gene knockoutsof mupO, mupU, mupV and macpE abolish PA-A production but not PA-B production, demonstrating that PA-B is a precursorto PA-A.[22]
Figure 5. MmpB is proposed to synthesize 9-HN with a 3-hydroxy-propionate starter unit and three malonyl-CoA extender units. The domain structure of MmpB is shown below alongside MupE, the proposed enoyl reductase required for complete saturation of 9-HN. ACP=acyl carrier protein, DH=dehydratase, ER=enoyl reductase, KR=ketoreductase, KS=ketosynthase, TE=thioesterase.

Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. Also present in mupirocin are pseudomonic acid B with an additional hydroxyl group at C8,[23] pseudomonic acid C with a double bond between C10 and C11, instead of the epoxide of PA-A,[24] and pseudomonic acid D with a double bond at C4` and C5` in the 9-hydroxy-nonanoic acid portion of mupirocin.[25]

Biosynthesis of pseudomonic acid A[edit]

The 74 kb mupirocin gene cluster contains six multi-domainenzymes and twenty-six other peptides (Table 1).[21] Four large multi-domain type I polyketide synthase (PKS) proteins are encoded, as well as several single function enzymes with sequence similarity to type II PKSs.[21] Therefore, it is believed that mupirocin is constructed by a mixed type I and type II PKS system. The mupirocin cluster exhibits an atypical acyltransferase (AT) organization, in that there are only two AT domains, and both are found on the same protein, MmpC. These AT domains are the only domains present on MmpC, while the other three type I PKS proteins contain no AT domains.[21] The mupirocin pathway also contains several tandem acyl carrier protein doublets or triplets. This may be an adaptation to increase the throughput rate or to bind multiple substrates simultaneously.[21]

Pseudomonic acid A is the product of an esterification between the 17C polyketide monic acid and the 9C fatty acid 9-hydroxy-nonanoic acid. The possibility that the entire molecule is assembled as a single polyketide with a Baeyer-Villigeroxidation inserting an oxygen into the carbon backbone has been ruled out because C1 of monic acid and C9' of 9-hydroxy-nonanoic acid are both derived from C1 of acetate.[26]

Monic acid biosynthesis[edit]

Biosynthesis of the 17C monic acid unit begins on MmpD (Figure 1).[21] One of the AT domains from MmpC may transfer an activated acetyl group from acetyl-Coenzyme A (CoA) to the first ACP domain. The chain is extended by malonyl-CoA, followed by a SAM-dependent methylation at C12 (see Figure 2 for PA-A numbering) and reduction of the B-keto group to an alcohol. The dehydration (DH) domain in module 1 is predicted to be non-functional due to a mutation in the conservedactive site region. Module 2 adds another two carbons by the malonyl-CoA extender unit, followed by ketoreduction (KR) and dehydration. Module three adds a malonyl-CoA extender unit, followed by SAM-dependent methylation at C8, ketoreduction, and dehydration. Module 4 extends the molecule with a malonyl-CoA unit followed by ketoreduction.

Assembly of monic acid is continued by the transfer of the 12C product of MmpD to MmpA.[21] Two more rounds of extension with malonyl-CoA units are achieved by module 5 and 6. Module 5 also contains a KR domain.

Post-PKS tailoring[edit]

The keto group at C3 is replaced with a methyl group in a multi-step reaction (Figure 3). MupG begins by decarboxylating a malonyl-ACP. The alpha carbon of the resulting acetyl-ACP is linked to C3 of the polyketide chain by MupH. This intermediate is dehydrated and decarboxylated by MupJ and MupK, respectively.[21]

The formation of the pyran ring requires many enzyme-mediated steps (Figure 4). The double bond between C8 and C9 is proposed to migrate to between C8 and C16.[22]Gene knockout experiments of mupO, mupU, mupV, and macpE have eliminated PA-A production.[22] PA-B production is not removed by these knockouts, demonstrating that PA-B is not created by hydroxylating PA-A. A knockout of mupW eliminated the pyran ring, identifying MupW as being involved in ring formation.[22] It is not known whether this occurs before or after the esterification of monic acid to 9-hydroxy-nonanoic acid.

The epoxide of PA-A at C10-11 is believed to be inserted after pyran formation by a cytochrome P450 such as MupO.[21] A gene knockout of mupO abolished PA-A production but PA-B, which also contains the C10-C11 epoxide, remained.[22] This indicates that MupO is either not involved or is not essential for this epoxidation step.

9-Hydroxy-nonanoic acid biosynthesis[edit]

The nine-carbon fatty acid9-hydroxy-nonanoic acid (9-HN) is derived as a separate compound and later esterified to monic acid to form pseudomonic acid. 13C labeled acetate feeding has shown that C1-C6 are constructed with acetate in the canonical fashion of fatty acid synthesis. C7' shows only C1 labeling of acetate, while C8' and C9' show a reversed pattern of 13C labeled acetate.[26] It is speculated that C7-C9 arises from a 3-hydroxypropionate starter unit, which is extended three times with malonyl-CoA and fully reduced to yield 9-HN. It has also been suggested that 9-HN is initiated by 3-hydroxy-3-methylglutaric acid (HMG). This latter theory was not supported by feeding of [3-14C] or [3,6-13C2]-HMG.[27]

It is proposed that MmpB to catalyzes the synthesis of 9-HN (Figure 5). MmpB contains a KS, KR, DH, 3 ACPs, and a thioesterase (TE) domain.[21] It does not contain an enoyl reductase (ER) domain, which would be required for the complete reduction to the nine-carbon fatty acid. MupE is a single-domain protein that shows sequence similarity to known ER domains and may complete the reaction.[21] It also remains possible that 9-hydroxy-nonanoic acid is derived partially or entirely from outside of the mupirocin cluster.


  1. ^Fleischer, Alan B. (2002). Emergency Dermatology: A Rapid Treatment Guide. McGraw Hill Professional. p. 173. ISBN . Archived from the original on 2017-09-10.
  2. ^"Drug Product Database Online Query". Retrieved 30 July 2019.
  3. ^AlHoufie, Sari Talal S.; Foster, Howard A. (1 August 2016). "Effects of sub-lethal concentrations of mupirocin on global transcription in Staphylococcus aureus 8325-4 and a model for the escape from inhibition". Journal of Medical Microbiology. 65 (8): 858–866. doi:10.1099/jmm.0.000270. PMID 27184545.
  4. ^ abcdefg"Mupirocin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ abWorld Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 298. hdl:10665/44053. ISBN .
  6. ^Khanna, Ramesh; Krediet, Raymond T. (2009). Nolph and Gokal's Textbook of Peritoneal Dialysis (3 ed.). Springer Science & Business Media. p. 421. ISBN . Archived from the original on 2017-09-10.
  7. ^Heggers, John P.; Robson, Martin C.; Phillips, Linda G. (1990). Quantitative Bacteriology: Its Role in the Armamentarium of the Surgeon. CRC Press. p. 118. ISBN . Archived from the original on 2017-09-10.
  8. ^World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^"The Top 300 of 2021". ClinCalc. Retrieved 18 February 2021.
  10. ^"Mupirocin - Drug Usage Statistics". ClinCalc. Retrieved 18 February 2021.
  11. ^ abHughes J, Mellows G (October 1978). "Inhibition of isoleucyl-transfer ribonucleic acid synthetase in Echerichia coli by pseudomonic acid". Biochem. J. 176 (1): 305–18. doi:10.1042/bj1760305. PMC 1186229. PMID 365175.
  12. ^"Product Monograph Bactroban"(PDF). Archived(PDF) from the original on September 24, 2015. Retrieved September 8, 2014.
  13. ^Troeman DPR, Van Hout D, Kluytmans JAJW (February 2019). "Antimicrobial approaches in the prevention of Staphylococcus aureus infections: a review". J. Antimicrob. Chemother. 74 (2): 281–294. doi:10.1093/jac/dky421. PMC 6337897. PMID 30376041.
  14. ^ abcdeCookson BD (January 1998). "The emergence of mupirocin resistance: a challenge to infection control and antibiotic prescribing practice". J. Antimicrob. Chemother. 41 (1): 11–8. doi:10.1093/jac/41.1.11. PMID 9511032.
  15. ^Worcester, Sharon (March 2008). "Topical MRSA Decolonization Is Warranted During Outbreaks". American College of Emergency Physicians. Elsevier Global Medical News. Archived from the original on 18 May 2014. Retrieved 18 November 2013.
  16. ^Yanagisawa T, Lee JT, Wu HC, Kawakami M (September 1994). "Relationship of protein structure of isoleucyl-tRNA synthetase with pseudomonic acid resistance of Escherichia coli. A proposed mode of action of pseudomonic acid as an inhibitor of isoleucyl-tRNA synthetase". J. Biol. Chem. 269 (39): 24304–9. doi:10.1016/S0021-9258(19)51082-1. PMID 7929087.
  17. ^Gilbart J, Perry CR, Slocombe B (January 1993). "High-level mupirocin resistance in Staphylococcus aureus: evidence for two distinct isoleucyl-tRNA synthetases". Antimicrob. Agents Chemother. 37 (1): 32–8. doi:10.1128/aac.37.1.32. PMC 187600. PMID 8431015.
  18. ^"Antibiotic Susceptibility of Propionibacterium acnes". 2011-06-11. Archived from the original on 2012-07-29. Retrieved 2012-08-27.
  19. ^Haseltine WA, Block R (May 1973). "Synthesis of Guanosine Tetra- and Pentaphosphate Requires the Presence of a Codon-Specific, Uncharged Transfer Ribonucleic Acid in the Acceptor Site of Ribosomes". Proc. Natl. Acad. Sci. U.S.A. 70 (5): 1564–8. Bibcode:1973PNAS...70.1564H. doi:10.1073/pnas.70.5.1564. PMC 433543. PMID 4576025.
  20. ^Tanaka K, Tamaki M, Watanabe S (November 1969). "Effect of furanomycin on the synthesis of isoleucyl-tRNA". Biochim. Biophys. Acta. 195 (1): 244–5. doi:10.1016/0005-2787(69)90621-2. PMID 4982424.
  21. ^ abcdefghijkEl-Sayed AK, Hothersall J, Cooper SM, Stephens E, Simpson TJ, Thomas CM (May 2003). "Characterization of the mupirocin biosynthesis gene cluster from Pseudomonas fluorescens NCIMB 10586". Chem. Biol. 10 (5): 419–30. doi:10.1016/S1074-5521(03)00091-7. PMID 12770824.
  22. ^ abcdeCooper SM, Laosripaiboon W, Rahman AS, et al. (July 2005). "Shift to Pseudomonic acid B production in P. fluorescens NCIMB10586 by mutation of mupirocin tailoring genes mupO, mupU, mupV, and macpE". Chem. Biol. 12 (7): 825–33. doi:10.1016/j.chembiol.2005.05.015. PMID 16039529.
  23. ^Chain EB, Mellows G (1977). "Pseudomonic acid. Part 3. Structure of pseudomonic acid B". J. Chem. Soc. Perkin Trans. 1 (3): 318–24. doi:10.1039/p19770000318. PMID 402373.
  24. ^Clayton, J; O'Hanlon, Peter J.; Rogers, Norman H. (1980). "The structure and configuration of pseudomonic acid C". Tetrahedron Letters. 21 (9): 881–884. doi:10.1016/S0040-4039(00)71533-4.
  25. ^O'Hanlon, PJ; Rogers, NH; Tyler, JW (1983). "The chemistry of pseudomonic acid. Part 6. Structure and preparation of pseudomonic acid D". Journal of the Chemical Society, Perkin Transactions 1: 2655–2657. doi:10.1039/P19830002655.
  26. ^ abFeline TC, Jones RB, Mellows G, Phillips L (1977). "Pseudomonic acid. Part 2. Biosynthesis of pseudomonic acid A". J. Chem. Soc. Perkin Trans. 1 (3): 309–18. doi:10.1039/p19770000309. PMID 402372.
  27. ^Martin, FM; Simpson, TJ (1989). "Biosynthetic studies on pseudomonic acid (mupirocin), a novel antibiotic metabolite of Pseudomonas fluorescens". Journal of the Chemical Society, Perkin Transactions 1 (1): 207–209. doi:10.1039/P19890000207.

External links[edit]

  • "Mupirocin". Drug Information Portal. U.S. National Library of Medicine.

You will also like:

mupirocin topical

What is the most important information I should know about mupirocin topical?

Follow all directions on your medicine label and package. Tell each of your healthcare providers about all your medical conditions, allergies, and all medicines you use.

What is mupirocin topical?

Mupirocin is an antibiotic that prevents bacteria from growing on your skin.

Mupirocin topical (for use on the skin) is used to treat skin infections such as impetigo (IM-pe-TYE-go) or a "Staph" infection of the skin.

Mupirocin topical may also be used for purposes not listed in this medication guide.

What should I discuss with my healthcare provider before using mupirocin topical?

You should not use this medicine if you are allergic to mupirocin.

To make sure mupirocin topical is safe for you, tell your doctor if you have ever had:

Do not use mupirocin topical on a child without medical advice. The cream should not be used on a child younger than 3 months old. The ointment may be used on a child as young as 2 months old.

It is not known whether this medicine will harm an unborn baby. Tell your doctor if you are pregnant.

It is not known whether mupirocin topical passes into breast milk or if it could harm a nursing baby. Tell your doctor if you are breast-feeding a baby. If you apply this medicine to your breast or nipple, wash the areas thoroughly before nursing your baby.

How should I use mupirocin topical?

Follow all directions on your prescription label. Do not use this medicine in larger or smaller amounts or for longer than recommended.

Do not take by mouth. Topical medicine is for use only on the skin. If this medicine gets in your eyes, nose, or mouth, rinse with water.

Wash your hands before and after applying mupirocin topical.

Clean and dry the affected skin area. Use a cotton swab or gauze pad to apply a small amount of mupirocin topical as directed.

Do not spread mupirocin topical over large areas of skin.

Mupirocin topical is usually applied 3 times per day for 10 days. Use only a small amount of the medicine.

Use a sterile gauze pad to cover the treated skin. Do not cover treated areas with a bandage, plastic wrap, or other covering that does not allow air to circulate.

Call your doctor if your symptoms do not improve within 3 to 5 days, or if your skin condition gets worse.

Use this medicine for the full prescribed length of time. Your symptoms may improve before the infection is completely cleared. Skipping doses may also increase your risk of further infection that is resistant to antibiotics.

Store at room temperature away from moisture and heat. Do not freeze. Keep the medicine tube tightly closed when not in use.

What happens if I miss a dose?

Apply the missed dose as soon as you remember. Skip the missed dose if it is almost time for your next dose. Do not use extra medicine to make up the missed dose.

What happens if I overdose?

An overdose of mupirocin topical is not expected to be dangerous. Seek emergency medical attention or call the Poison Help line at 1-800-222-1222 if anyone has accidentally swallowed the medication.

What should I avoid while using mupirocin topical?

Antibiotic medicines can cause diarrhea, which may be a sign of a new infection. If you have diarrhea that is watery or bloody, call your doctor. Do not use anti-diarrhea medicine unless your doctor tells you to.

Avoid getting this medicine in your eyes, mouth, or nose. A separate product called mupirocin nasal is made for use in the nose. Mupirocin topical is for use only on the skin.

Avoid using other medications on the areas you treat with mupirocin topical unless your doctor tells you to.

What other drugs will affect mupirocin topical?

It is not likely that other drugs you take orally or inject will have an effect on topically applied mupirocin. But many drugs can interact with each other. Tell each of your health care providers about all medicines you use, including prescription and over-the-counter medicines, vitamins, and herbal products.

Where can I get more information?

Your pharmacist can provide more information about mupirocin topical.

Remember, keep this and all other medicines out of the reach of children, never share your medicines with others, and use this medication only for the indication prescribed.

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