Mecillinam

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Mecillinam
Clinical data
Trade namesCoactin, Leo, Selexid, Selexidin
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Appears safe in pregnancy[1]
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNegligible
Protein binding5 to 10%
MetabolismSome hepatic metabolism
Elimination half-life1 to 3 hours
ExcretionRenal and biliary, mostly unchanged
Identifiers
  • (2S,5R,6R)-6-[(E/Z)-(Azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
 ☒NcheckY (what is this?)  (verify)

Mecillinam (

penicillin binding protein 2 (PBP2),[2] and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever.[3][4] Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam
.

Medical uses

Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially urinary tract infections which are most commonly caused by Escherichia coli.[5] Mecillinam is active against most pathogenic Gram-negative bacteria, except Pseudomonas aeruginosa and some species of Proteus.[6] Several studies have also found it to be as effective as other antibiotics for treating Staphylococcus saprophyticus infection, though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.[1]

Worldwide

resistance to mecillinam in bacteria causing urinary tract infection has remained very low since its introduction; a 2003 study conducted in 16 European countries and Canada found resistance to range from 1.2% (Escherichia coli) to 5.2% (Proteus mirabilis).[7] Another large study conducted in Europe and Brazil obtained similar results — 95.9% of E. coli strains, for instance, were sensitive to mecillinam.[8]

Adverse effects

See also:
Beta-lactam antibiotic: Adverse effects

The adverse effect profile of mecillinam is similar to that of other penicillins.[2] Its most common side effects are rash and gastrointestinal upset, including nausea and vomiting.[1]

History

With the codename FL 1060, mecillinam was developed by the Danish

LEO Pharma). It was first described in the scientific literature in a 1972 paper.[9][10]

References

  1. ^
    PMID 10969050
    .
  2. ^
    S2CID 46561080
    .
  3. PMID 820402
    .
  4. PMID 408321
    .
  5. S2CID 115699373
    .
  6. ^ Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. Archived from the original on February 4, 2009. Retrieved September 1, 2008. Retrieved on August 31, 2008. Freely available with registration.
  7. PMID 12493789
    .
  8. PMID 18511178
    .
  9. S2CID 4293996
    .
  10. PMID 170856
    .
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