Carfecillin

Carfecillin
Clinical data
ATC code	G01AA08 (WHO) ;
Identifiers
	IUPAC name (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[ [3-oxo-3-(phenoxy)-2-phenylpropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	27025-49-6;
PubChem CID	33672;
ChemSpider	31054 ;
UNII	9UU4XDB74X;
ChEBI	CHEBI:3414 ;
ChEMBL	ChEMBL1095283 ;
CompTox Dashboard (EPA)	DTXSID10891704 ;
ECHA InfoCard	100.043.778
Chemical and physical data
Formula	C23H22N2O6S
Molar mass	454.50 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)Oc2ccccc2)[C@H]4SC3(C)C;
	InChI InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1 ; Key:NZDASSHFKWDBBU-KVMCETHSSA-N ;
	(verify)

Carfecillin is a beta-lactam antibiotic. It is a phenyl derivative of carbenicillin, acting as a prodrug.^[1]

References

^ 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.

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Clinical data

ATC code	G01AA08 (WHO)
Identifiers
IUPAC name (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[ [3-oxo-3-(phenoxy)-2-phenylpropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number	27025-49-6
PubChem CID	33672
ChemSpider	31054^Y
UNII	9UU4XDB74X
ChEBI	CHEBI:3414^Y
ChEMBL	ChEMBL1095283^Y
CompTox Dashboard (EPA)	DTXSID10891704
ECHA InfoCard	100.043.778
Chemical and physical data
Formula	C₂₃H₂₂N₂O₆S
Molar mass	454.50 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)Oc2ccccc2)[C@H]4SC3(C)C
InChI InChI=1S/C23H22N2O6S/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29)/t15?,16-,17+,20-/m1/s1^Y Key:NZDASSHFKWDBBU-KVMCETHSSA-N^Y
(verify)