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
Trade names	Intracef, Velocef
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Legal status	℞ (Prescription only)
Routes of administration	Oral, IM, IV
Pharmacokinetic data
Bioavailability	Well absorbed
Protein binding	<10%
Metabolism	Nil
Biological half-life	0.9 hours
Excretion	Renal, unchanged
Identifiers
CAS Number	38821-53-3 Y
ATC code	J01DB09 (WHO)
PubChem	CID: 38103
IUPHAR/BPS	4830
DrugBank	DB01333 Y
ChemSpider	34933 Y
UNII	9YA6SX5S4D Y
KEGG	D00264 Y
ChEBI	CHEBI:3547 Y
ChEMBL	CHEMBL1604 Y
Chemical data
Formula	C16H19N3O4S
Molecular mass	349.406 g/mol
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
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Cefradine (INN) (formerly cephradine BAN) is a first generation cephalosporin antibiotic.

Indications

It has similar spectrum of activity to cefalexin. RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). (Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Velosef is generally effective in the eradication of streptococci from the nasopharynx; substantial data establishing the efficacy of Velosef in the subsequent prevention of rheumatic fever are not available at present.) OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). The high concentrations of cephradine achievable in the urinary tract will be effective against many strains of enterococci for which disc susceptibility studies indicate relative resistance. It is to be noted that among beta-lactam antibiotics, ampicillin is the drug of choice for enterococcal urinary tract (E. faecalis) infection.

Formulations

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

Brand Names

International Brands Velocef, Infexin (by Merck Pvt, Ltd) Intracef (by Beximco Pharma) SEFRIL(The ACME laboratories Ltd., Bangladesh), REOCEF(Rephco Pharmaceuticals Ltd., Bangladesh). Lebac (by Square pharmaceuticals Ltd., Bangladesh).. It is not approved by the FDA for use in the United States.

Synthesis

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.

Cefradin synthesis: U.S. Patent 3,485,819 DE 1931722 

Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected using tert-Butoxycarbonylazide and activated for amide fromation 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).

See also

• Cephapirin
• Cephacetrile
• Cefamandole
• Ampicillin (Has the same chemical formula)

References

• British National Formulary 45 March 2003