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Carindacillin

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Carindacillin
Clinical data
AHFS/Drugs.comInternational 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
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H26N2O6S
Molar mass494.56g·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 ascarbenicillin indanyl(USAN), is apenicillinantibiotic.It is aprodrugofcarbenicillin.[1]

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

Pharmacokinetics

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

References

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  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.PMC444190.PMID4558137.
  2. ^"Drugs@FDA: FDA-Approved Drugs CARBENICILLIN INDANYL SODIUM".www.accessdata.fda.gov.Retrieved2022-07-29.
  3. ^Pfizer (2008)."GEOCILLIN® carbenicillin indanyl sodium tablets label"(PDF).