Carbenicillin

Carbenicillin
Clinical data
Trade names	Geocillin; Pyopen
Other names	CB
AHFS/Drugs.com	Monograph
Pregnancy; category	Passes into breast milk;
Routes of; administration	Oral, parenteral
ATC code	J01CA03 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	30 to 40%
Protein binding	30 to 60%
Metabolism	Minimal
Elimination half-life	1 hour
Excretion	Renal (30 to 40%)
Identifiers
	IUPAC name (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-; 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]; heptane-2-carboxylic acid;
CAS Number	4697-36-3 ;
PubChem CID	20824;
DrugBank	DB00578 ;
ChemSpider	19599 ;
UNII	G42ZU72N5G;
KEGG	D07614 ;
ChEBI	CHEBI:3393 ;
ChEMBL	ChEMBL1214 ;
CompTox Dashboard (EPA)	DTXSID6048464 ;
ECHA InfoCard	100.022.882
Chemical and physical data
Formula	C17H18N2O6S
Molar mass	378.40 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)O)[C@H]3SC2(C)C;
	InChI InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 ; Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N ;
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Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins.^[2] It was discovered by scientists at Beecham and marketed as Pyopen. It has Gram-negative coverage which includes Pseudomonas aeruginosa but limited Gram-positive coverage. The carboxypenicillins are susceptible to degradation by beta-lactamase enzymes, although they are more resistant than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.

^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
^ Basker MJ, Comber KR, Sutherland R, Valler GH (1977). "Carfecillin: antibacterial activity in vitro and in vivo". Chemotherapy. 23 (6): 424–35. doi:10.1159/000222012. PMID 21771.