Carindacillin

Title: Carindacillin
CAS Registry Number: 35531-88-5
CAS Name: (2S,5R,6R)-6-[[3-[(2,3-Dihydro-1H-inden-5-yl)oxy]-1,3-dioxo-2-phenylpropyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-2-phenylmalonamic acid 1-(5-indanyl) ester; 6-[2-(5-indanyloxycarbonyl)phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 1-(5-indanyl) N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-2-phenylmalonamate; 6-[2-phenyl-2-(5-indanyloxycarbonyl)acetamido]penicillanic acid; 6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 6-(5-indanyl ester); a-(5-indanyloxycarbonyl)benzylpenicillin; carbenicillin indanyl ester
Manufacturers' Codes: CP-15464
Molecular Formula: C26H26N2O6S
Molecular Weight: 494.56
Percent Composition: C 63.14%, H 5.30%, N 5.66%, O 19.41%, S 6.48%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: K. Butler, ZA 6900060; idem, US 3679801 (1969, 1972 both to Pfizer). New process: S. Nakanishi, US 3759898 (1973 to Pfizer). Activity studies: Butler, Del. Med. J. 43, 366 (1971); English et al., Antimicrob. Agents Chemother. 1, 185 (1972). Clinical evaluation: Wallace et al., Antimicrob. Agents Chemother. 1970, 223; Bran et al., Clin. Pharmacol. Ther. 12, 525 (1971); Indanyl Carbenicillin, H. Swarz, F. E. Storari, Eds. (Am. Elsevier, New York, 1974) 100 pp.
Derivative Type: Sodium salt
CAS Registry Number: 26605-69-6
Manufacturers' Codes: CP-15464-2
Trademarks: Carindapen (Pfizer); Geocillin (Roerig); G.U.-Pen (Pfizer)
Molecular Formula: C26H25N2NaO6S
Molecular Weight: 516.54
Percent Composition: C 60.46%, H 4.88%, N 5.42%, Na 4.45%, O 18.58%, S 6.21%
Properties: mp 207-213°.
Melting point: mp 207-213°
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
Cariporide Carlsbad Salt Artificial Carminic Acid Carmofur Carmoxirole

Carindacillin
Carindacillin.png
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Oral
Identifiers
CAS number 26605-69-6
ATC code J01CA05
PubChem CID 93184
ChemSpider 391995
UNII 5V278481KE YesY
ChEMBL CHEMBL1200991
Chemical data
Formula C26H26N2O6S 
Mol. mass 494.55 g/mol

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 is marketed by Pfizer under the brand name Geocillin.