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Pivmecillinam

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Pivmecillinam
Pivmecillinam.svg
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category

  • Appears safe in pregnancy[1]
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow
Protein binding5 to 10% (as mecillinam)
MetabolismPivmecillinam is hydrolyzed to mecillinam
Elimination half-life1 to 3 hours
ExcretionRenal and biliary, mostly as mecillinam
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H33N3O5S
Molar mass439.569 g/mol g·mol−1
3D model (JSmol)
 ☒NcheckY (what is this?)  (verify)

Pivmecillinam (INN) or amdinocillin pivoxil (USAN, trade names Selexid, Penomax and Coactabs) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam. Neither drug is available in the United States.[2]

Pivmecillinam is only considered to be active against Gram-negative bacteria, and is used primarily in the treatment of lower urinary tract infections. In the Nordic countries, it has been widely used in that indication since the 1970s. It has been proposed as the first-line drug of choice for empirical treatment of acute cystitis.[1][3] It has also been used to treat paratyphoid fever and shigellosis.[4]

Activity

Adverse effects

The adverse effect profile of pivmecillinam is similar to that of other penicillins. The most common side effects of mecillinam use are rash and gastrointestinal upset, including nausea and vomiting.[1][5]

Prodrugs that release pivalic acid when broken down by the body — such as pivmecillinam, pivampicillin and cefditoren pivoxil — have long been known to deplete levels of carnitine.[6][7] This is not due to the drug itself, but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine,[8] it is unlikely to be of clinical significance;[7] long-term use, however, appears problematic and is not recommended.[7][9][10]

References

  1. 1.0 1.1 1.2
  2. Retrieved on August 31, 2008. Freely available with registration.
  3. Retrieved on August 31, 2008.
  4. 7.0 7.1 7.2
Skeletal formula of mecillinam, the active moiety of pivmecillinam

Comprehensive list of medications or pharmaceutical drugs used in the United States with their NDC or national drug code, brand name, dosage, forms of administration etc. sorted alphabetically.

See also

External links

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