e-Drug3D

1029

CEFUROXIME

INN
CEFUROXIME

(is an active metabolite)

cas 55268-75-2

CLASS

ANTIINFECTIVES
ANTIBIOTIC
ANTIBACTERIAL
CEPHALOSPORINS

ROUTE (list)

INTRAMUSCULAR INTRAVENOUS INJECTION

ATC code

J01DC02
S01AA27
J01DC52
J01RA03

PK parameters

Tmax 2.5 HOUR
Cmax 32 MICROMOLAR (1 GRAM)
VD 9.7 LITER (65 KILOGRAM)
Cl 8.6 LITER / HOUR (65 KILOGRAM)
PPB 50 PERCENT
t1/2 1.3 HOUR

Target

TARGET PENICILLIN-BINDING PROTEINS 1A/1B

PDB
4KOV (CRYSTAL STRUCTURE OF A GNAT SUPERFAMILY ACETYLTRANSFERASE PA4794 IN COMPLEX WITH CEFUROXIME)

Ligand code = KOV (link to the list of PDB complexes)

Download experimental 3D coordinates of KOV with added hydrogens

DrugCentral

Bacterial penicillin-binding protein UNIPROT P02918 mrcA

Download SDF file

(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2E)-2-furan-2-yl-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Formula:
C16H16N4O8S

Calculated chemical properties:

MW 423.39
NB_atoms 29
XLogP -1.87
PSA 153.792
NB_HD 3
NB_HA 12
fsp3 0.31
Lipinski(0=no;1=yes) 0

FDA
NDA 050558 (label) INN (CEFUROXIME SODIUM) ZINACEF (PAI HOLDINGS PHARM) APPROVAL= AP YEAR= 1983 DISCONTINUED
NDA 062590 (pdf not found) INN (CEFUROXIME SODIUM) KEFUROX IN PLASTIC CONTAINER (LILLY) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 062591 (pdf not found) INN (CEFUROXIME SODIUM) KEFUROX (ACS DOBFAR) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 062592 (pdf not found) INN (CEFUROXIME SODIUM) KEFUROX (LILLY) APPROVAL= AP YEAR= 1986 DISCONTINUED
NDA 050643 (label) INN (CEFUROXIME SODIUM) ZINACEF IN PLASTIC CONTAINER (PAI HOLDINGS PHARM) APPROVAL= AP YEAR= 1989 DISCONTINUED
NDA 064035 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (WATSON LABS INC) APPROVAL= AP YEAR= 1993 DISCONTINUED
NDA 064036 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (WATSON LABS INC) APPROVAL= AP YEAR= 1993 DISCONTINUED
NDA 064124 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (ACS DOBFAR SPA) APPROVAL= AP YEAR= 1997 DISCONTINUED
NDA 064125 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (ACS DOBFAR SPA) APPROVAL= AP YEAR= 1997
NDA 064191 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (TEVA PHARMS) APPROVAL= AP YEAR= 1998 DISCONTINUED
NDA 064192 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (TEVA PHARMS) APPROVAL= AP YEAR= 1998 DISCONTINUED
NDA 065002 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (FRESENIUS KABI USA) APPROVAL= AP YEAR= 1998 DISCONTINUED
NDA 050780 (label) INN (CEFUROXIME SODIUM) CEFUROXIME AND DEXTROSE IN DUPLEX CONTAINER (B BRAUN) APPROVAL= AP YEAR= 2001 DISCONTINUED
NDA 065001 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (FRESENIUS KABI USA) APPROVAL= AP YEAR= 2001 DISCONTINUED
NDA 065046 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (HIKMA) APPROVAL= AP YEAR= 2004 DISCONTINUED
NDA 065048 (pdf not found) INN (CEFUROXIME) CEFUROXIME (HIKMA) APPROVAL= AP YEAR= 2004
NDA 065483 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (HOSPIRA INC) APPROVAL= AP YEAR= 2008 DISCONTINUED
NDA 065484 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (HOSPIRA INC) APPROVAL= AP YEAR= 2008 DISCONTINUED
NDA 065503 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM (HOSPIRA INC) APPROVAL= AP YEAR= 2008 DISCONTINUED
NDA 065251 (pdf not found) INN (CEFUROXIME SODIUM) CEFUROXIME SODIUM IN PLASTIC CONTAINER (SAMSON MEDCL) APPROVAL= AP YEAR= 2009 DISCONTINUED

Other links:

PubChem
ChemicalProbes

U.S. repository of Clinical Trials

VigiAccess
SIDER side effects

ChemSynthesis
Patent@SureChEMBL

e-Drug3D

1030

CEFUROXIME AXETIL

INN
CEFUROXIME AXETIL

(has an active metabolite)

cas 64544-07-6

CLASS

ANTIINFECTIVES
ANTIBACTERIAL
ANTIBIOTIC
CEPHALOSPORINS

ROUTE (list)

ORAL

ATC code

J01DC02
S01AA27
J01DC52
J01RA03

PK parameters

Target

TARGET PENICILLIN-BINDING PROTEINS 1A/1B

DrugCentral

Bacterial penicillin-binding protein UNIPROT P02918 mrcA

Download SDF file

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, 1-(acetyloxy)ethyl ester, (6R,7R)-

Formula:
C20H22N4O10S

Calculated chemical properties:

MW 510.49
NB_atoms 35
XLogP -0.17
PSA 172.757
NB_HD 3
NB_HA 14
fsp3 0.40
Lipinski(0=no;1=yes) 0

FDA
NDA 050605 (label) INN (CEFUROXIME AXETIL) CEFTIN (GLAXOSMITHKLINE) APPROVAL= AP YEAR= 1987 DISCONTINUED
NDA 050672 (label) INN (CEFUROXIME AXETIL) CEFTIN (GLAXOSMITHKLINE) APPROVAL= AP YEAR= 1994 DISCONTINUED
NDA 065043 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (RANBAXY LABS LTD) APPROVAL= AP YEAR= 2002 DISCONTINUED
NDA 065069 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (APOTEX) APPROVAL= AP YEAR= 2002 DISCONTINUED
NDA 065118 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (SUN PHARM INDS LTD) APPROVAL= AP YEAR= 2003 DISCONTINUED
NDA 065126 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (FOSUN PHARMA) APPROVAL= AP YEAR= 2003 DISCONTINUED
NDA 065135 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (LUPIN) APPROVAL= AP YEAR= 2003 DISCONTINUED
NDA 065190 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (ANI PHARMS) APPROVAL= AP YEAR= 2004 DISCONTINUED
NDA 065166 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (CHARTWELL RX) APPROVAL= AP YEAR= 2005
NDA 065308 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (AUROBINDO PHARMA) APPROVAL= AP YEAR= 2006
NDA 065323 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (SUN PHARM INDS LTD) APPROVAL= AP YEAR= 2008 DISCONTINUED
NDA 065359 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (ANDA REPOSITORY) APPROVAL= AP YEAR= 2008
NDA 065496 (pdf not found) INN (CEFUROXIME AXETIL) CEFUROXIME AXETIL (ALKEM LABS LTD) APPROVAL= AP YEAR= 2010