Cefradine

Cefradine

Systematic (IUPAC) name
(6R,7R)-7-{[(2R)-2-amino-2-(1-cyclohexa-1,4- dienyl)acetyl]amino}-3-methyl-8-oxo-5-thia- 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral, IM, IV
Pharmacokinetic data
Bioavailability	Well absorbed
Protein binding	<10%
Metabolism	Nil
Half-life	0.9 hours
Excretion	Renal, unchanged
Identifiers
CAS number	38821-53-3
ATC code	J01DB09
PubChem	CID 38103
DrugBank	DB01333
ChemSpider	34933^Y
UNII	9YA6SX5S4D^Y
KEGG	D00264^Y
ChEBI	CHEBI:3547^Y
ChEMBL	CHEMBL1604^Y
Chemical data
Formula	C₁₆H₁₉N₃O₄S
Mol. mass	349.406 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1^Y Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N^Y
Y(what is this?) (verify)

Cefradine (INN) (formerly cephradine BAN) is a first generation cephalosporin antibiotic.

Indications

It has similar spectrum of activity to cefalexin.

Formulations

Capsules containing 250 mg or 500 mg, Syrup containing 250 mg/5 ml, or vials for injection containing 500 mg or 1 g.

References

British National Formulary 45 March 2003

Antibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular

inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)

Glycopeptide

inhibit PG chain elongation: Vancomycin^# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins
(penams)

Extended sp.

aminopenicillins: Amoxicillin^# • Ampicillin^# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin

carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin

ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin

other: Mecillinam (Pivmecillinam) • Sulbenicillin

Narrow sp.

β-lactamase sensitive	Benzylpenicillin (G)^#: Clometocillin • Benzathine benzylpenicillin^# • Procaine benzylpenicillin^# • Azidocillin • Penamecillin Phenoxymethylpenicillin (V)^#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin

β-lactamase resistant	Cloxacillin^# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/Cephamycins
(cephems)

1st (P Ec K)	Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)	Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd	Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)	Cefepime • Cefozopran • Cefpirome • Cefquinome

5th	Ceftobiprole • Ceftaroline fosamil

Veterinary	Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Nocardicin A

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other

polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)