Mupirocin

Introduction
Mupirocin (trade names Bactroban, Centany) It is used topically and is effective against
Gram-positive bacteria, including MRSA or Methicillin-resistant Staphylococcus aureus
Mupirocin is inactive for most anaerobic bacteria, mycobacteria, mycoplasma, chlamydia,
yeast and fungi.
Mupirocin (pseudomonic acid A), an antibiotic produced by Pseudomonasfluorescens,
showed a high level of activity against staphylococci and streptococci and against certain
gram-negative bacteria, including Haemophilus influenzae and Neisseria gonorrhoeae, but
was much less active against most gram-negative bacilli and anaerobes. Nearly all clinical
isolates of Staphylococcus aureus and Staphylococcus epidermidis, including multiply
resistant strains, were susceptible (mupirocin MIC, o0.5 ,ug/ml). There was no crossresistance between mupirocin and clinically available antibiotics, and the selection of
resistant variants in vitro occurred at a low frequency.
An advantageous feature of this antibiotic is that it has very low toxicity both for humans and
animals and it is negative in the Ames test. Pseudomonic acid A is presently used in human
therapy, in various formulations, for the treatment of skin infections (e.g. impetigo,
pyoderma), nose and external ear infections, acne, burns, eczema, psoriasis, in case of
ulceration for treatment of secondary infections, and for prevention of hospital infections.
The chemical structure of pseudomonic acid A is 9-{4[5S(2S,3S-epoxy-5S-hydroxy-4Smethylhexyl)-3R,4R-dihydroxy-tetrahydropyran-2S-yl]-3-methylbut-2(E)enoyloxy}nonanoic acid [E. B. Chain and G. Mellows, J. C. S. Chem. Comm. 847-848
(1974); R. G. Alexander, J. P. Clayton, K. Luk, N. H. Rogers, T. J. King, J. C. S. Perkin I.
561-565 (1978)], as depicted by formula (I):

(Figure 1 shows structural formula of mupirocin)

Process
Processes are provided for preparing mupirocin calcium dihydrate from pseudomonic acid in
a two phase system by using an organic carboxylate. A highly pure composition of
amorphous mupirocin calcium is provided, and processes for its preparation by solvent
removal, lyophilization and precipitation with use of an anti-solvent. Pharmaceutical
compositions of amorphous form, and methods of using them to treat infections are also
provided. Also provided are combined processes for preparing mupirocin calcium dihydrate
and amorphous, by producing amorphous form first, followed by conversion of amorphous
form into the dihydrate through crystallization from an aqueous solution. Also provided are
processes for removing the water of crystallization of the dihydrate to obtain mupirocin
calcium anhydrate.

Uses
Mupirocin is used in the treatment of superficial skin infections and in controlling the spread
of methicillinresistant Staphylococcus aureus (MRSA). in healthy people, although recolonization is seen in up to 67% of subjects 6 months later.2,3 Short-term intranasal
mupirocin application may reduce post-operative infection rates and vascular and continuous
ambulatory peritoneal dialysis (CAPD) catheter-related infections in dialysis patients.46

Prescription and 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 ointment 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.
Avoid using this medication around your eyes, nose, mouth, or on large areas of damaged or
broken skin unless otherwise directed by your doctor. If you accidentally get it in your eyes,
nose, or mouth, rinse well with plenty of water.

Precautions
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 (such as polyethylene
glycol found in some brands), 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, especially
of: kidney disease (if you are using a brand of mupirocin that contains polyethylene glycol).
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.

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 (Clostridium difficileassociated diarrhea) due to a type of resistant bacteria. 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.
Do not use anti-diarrhea products or narcotic pain medications if you have any of these
symptoms because these products may make them 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.

Other Info
Mupirocin calcium, an antibiotic derived from pseudomonic acid is currently marketed in the
United States as Bactroban. Bactroban is recommended for treatment of secondarily
infected traumatic skin lesions caused by strains of Stephylococcus aureus and Streptococcus
pyogenes. Bactroban is sold as a topical cream or a nasal ointment and has a calcium salt
strength of 2% equivalent base. According to the maker of Bactroban, mupirocin calcium
could be administered orally at 500 mg, and intravenously at 250 mg without any major side
effects.

Reference
Mupirocin Topical, (n.d). WebMD Retrieved from: http://www.webmd.com/drugs/2/drug6180/mupirocin-topical/details#
Journal of Antimicrobial Chemotherapy, (2003). Mupirocin and Staphylococcus aureus: a
recent paradigm of emerging antibiotic resistance Retrieved from:
http://jac.oxfordjournals.org/content/51/3/613.full.pdf
Processes for preparing Crystalline and amorphous Mupirocin Calcium, (2010) Retrieved from:
https://www.google.com/patents/US7737177
"Product Monograph Bactroban" (PDF). (2014) Retrieved from:
http://www.skintherapyletter.com/download/BactOintPM.pdf
Figure 1 Image Retrived from:
https://en.wikipedia.org/wiki/Mupirocin#/media/File:Mupirocin_structure.png

Project in
Biotechnology
(Antibiotics

Submitted by:
Landhel Olsel G. Lobo

Submitted to:
Joan B. Callope