Carindacillin

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| 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

| image = Carindacillin.svg

| tradename =

| Drugs.com = {{drugs.com|international|carindacillin}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

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| index2_label = salt

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 26605-69-6

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 4OUL81K2RT

| CAS_number = 35531-88-5

| ATC_prefix = J01

| ATC_suffix = CA05

| ATC_supplemental =

| PubChem = 93184

| DrugBank =

| ChEMBL = 1200991

| ChemSpiderID = 391995

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5V278481KE

| chemical_formula =

| C=26 | H=26 | N=2 | O=6 | S=1

| 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.{{cite journal |vauthors=English AR, Retsema JA, Ray VA, Lynch JE |title=Carbenicillin indanyl sodium, an orally active derivative of carbenicillin |journal=Antimicrob. Agents Chemother. |volume=1 |issue=3 |pages=185–91 |date=March 1972 |pmid=4558137 |pmc=444190 |doi= 10.1128/aac.1.3.185|url=}}

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.{{Cite web |title=Drugs@FDA: FDA-Approved Drugs CARBENICILLIN INDANYL SODIUM |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&varApplNo=050435 |archive-url=https://web.archive.org/web/20220729071701/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&varApplNo=050435 |url-status=dead |archive-date=July 29, 2022 |access-date=2022-07-29 |website=www.accessdata.fda.gov}}