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Carindacillin

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Chemical compound

Pharmaceutical compound
Carindacillin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (2S,5R,6R)-6-(amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26N2O6S
Molar mass494.56 g·mol
3D model (JSmol)
SMILES
  • .O=C()4N5C(=O)(NC(=O)C(c1ccccc1)C(=O)Oc2cc3c(cc2)CCC3)5SC4(C)C

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

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.

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.

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).
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other


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