Carindacillin

Last updated
Carindacillin
Carindacillin.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (2S,5R,6R)-6-([3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C26H26N2O6S
Molar mass 494.56 g·mol−1
3D model (JSmol)
  • [Na+].O=C([O-])[C@@H]4N5C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)Oc2cc3c(cc2)CCC3)[C@H]5SC4(C)C

Carindacillin (INN), also known as carbenicillin indanyl (USAN), is a penicillin antibiotic. It is a prodrug of carbenicillin. [1]

It is administered orally, as the sodium salt. It was formerly marketed in the United States by Pfizer under the brand name Geocillin. Pfizer withdrew Carindacillin from the U.S. market sometime after 2008. [2]

Pharmacokinetics

Shortly after absorption via the small intestine, Carindacillin is hydrolyzed into Carbenicillin. Carbenicillin acts by interfering with final cell wall synthesis in susceptible bacteria, including Pseudomonas aeruginosa, Escherichia coli, and some Proteus. The most common adverse effects include nausea, bad taste, diarrhea, vomiting, flatulence, and glossitis. Carindacillin was approved for use in adults in the treatment of prostatitis and urinary tract infections. Dosing was between 2000 and 4000 mg daily, divided into equally spaced doses. [3]

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References

  1. English AR, Retsema JA, Ray VA, Lynch JE (March 1972). "Carbenicillin indanyl sodium, an orally active derivative of carbenicillin". Antimicrob. Agents Chemother. 1 (3): 185–91. doi:10.1128/aac.1.3.185. PMC   444190 . PMID   4558137.
  2. "Drugs@FDA: FDA-Approved Drugs CARBENICILLIN INDANYL SODIUM". www.accessdata.fda.gov. Retrieved 2022-07-29.
  3. Pfizer (2008). "GEOCILLIN® carbenicillin indanyl sodium tablets label" (PDF).