Cefaradine

Cefradine

Clinical data
Trade names	Intracef, Velocef
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Routes of administration	Oral, IM, IV
ATC code	J01DB09 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Well absorbed
Protein binding	<10%
Metabolism	Nil
Biological half-life	0.9 hours
Excretion	Renal, unchanged
Identifiers
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
CAS Number	38821-53-3 Y
PubChem CID	38103
IUPHAR/BPS	4830
DrugBank	DB01333 Y
ChemSpider	34933 Y
UNII	9YA6SX5S4D
KEGG	D00264 Y
ChEBI	CHEBI:3547 Y
ChEMBL	CHEMBL1604 Y
ECHA InfoCard	100.049.199
Chemical and physical data
Formula	C16H19N3O4S
Molar mass	349.406 g/mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](C/3=C/C\C=C/C\3)N)C)C(=O)O
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

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

Cefradine has similar spectrum of activity to cefalexin. It is used in the following instances:

Cefradine is distributed in the form of capsules containing 250 mg or 500 mg, as a syrup containing 250 mg/5 ml, or in vials for injection containing 500 mg or 1 g.

The antibiotic is produced under a wide number of brand names across the world.

Cefradine is known as Cefradina in Portuguese and Spanish and is produced by the following companies under this name: AC Farma, Peru; Andromaco, Chile; Anglopharma, Colombia; AZ Pharma, Colombia; Biogalenic, Venezuela; Bussié, Colombia; Elter - Medicamentos Genéricos, Venezuela; Farmindustria, Peru; Genfar, Colombia, Honduras and Peru; La Sante, Peru; La Santé, Colombia; Labesfal, Portugal; Lafrancol, Colombia; LCG, Peru; Marfan, Peru; Memphis, Colombia; Mintlab, Chile; MK, Colombia; Ophalac, Colombia; Procaps, Colombia and Vitalis, Colombia and Peru.

It is not approved by the FDA for use in the United States.

Noting that 1,4-cyclohexadiene rings are nearly as planar as benzene rings but of greatly different reactivity, a cephalosporin was synthesized with such a moiety.

Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected using tert-Butoxycarbonylazide and activated for amide formation via the mixed anhydride method using isobutylchloroformate to give 3. Mixed anhydride 3 reacted readily with 7-Aminodesacetoxycephalosporanic acid to give, after deblocking, cephadrine (5).