Carindacillin

Carindacillin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	J01CA05 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (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	35531-88-5; salt: 26605-69-6 ;
PubChem CID	93184;
ChemSpider	391995;
UNII	5V278481KE; salt: 4OUL81K2RT ;
ChEMBL	ChEMBL1200991;
CompTox Dashboard (EPA)	DTXSID6048705 ;
Chemical and physical data
Formula	C26H26N2O6S
Molar mass	494.56 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [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]

References

^ 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.
^ "Drugs@FDA: FDA-Approved Drugs CARBENICILLIN INDANYL SODIUM". www.accessdata.fda.gov. Retrieved 2022-07-29.
^ Pfizer (2008). "GEOCILLIN® carbenicillin indanyl sodium tablets label" (PDF).

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[pmid4558137-1] 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).

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J01CA05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (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	35531-88-5 salt: 26605-69-6^Y
PubChem CID	93184
ChemSpider	391995
UNII	5V278481KE salt: 4OUL81K2RT^Y
ChEMBL	ChEMBL1200991
CompTox Dashboard (EPA)	DTXSID6048705
Chemical and physical data
Formula	C₂₆H₂₆N₂O₆S
Molar mass	494.56 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [Na+].O=C([O-])[C@@H]4N5C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)Oc2cc3c(cc2)CCC3)[C@H]5SC4(C)C