Cefradine

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
Elimination 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 ;
PubChem CID	38103;
IUPHAR/BPS	4830;
DrugBank	DB01333 ;
ChemSpider	34933 ;
UNII	9YA6SX5S4D;
KEGG	D00264 ;
ChEBI	CHEBI:3547 ;
ChEMBL	ChEMBL1604 ;
CompTox Dashboard (EPA)	DTXSID4022785 ;
ECHA InfoCard	100.049.199
Chemical and physical data
Formula	C16H19N3O4S
Molar mass	349.41 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	140 to 142 °C (284 to 288 °F) (dec.)
	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 ; Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N ;
	(verify)

Cefradine (INN) or cephradine (BAN) is a first generation cephalosporin antibiotic.^[1]

Indications

Respiratory tract infections (such as tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia).^{[note 1]}
Otitis media caused by group A beta-hemolytic streptococci, S. 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 and Klebsiella species.

Formulations

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.^{[citation needed]}

It is not approved by the FDA for use in the United States.^{[citation needed]}

Synthesis

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, cephradine (5).

Cefradin synthesis:^[2]^[3]^[4]

Production names

The antibiotic is produced under many brand names across the world.^[5]

Bangladesh: Ancef, Ancef forte, Aphrin, Avlosef, Cefadin, Cephadin, Cephran, Cephran-DS, Cusef, Cusef DS, Dicef , Dicef forte, Dolocef, Efrad, Elocef, Extracef, Extracef-DS, Intracef, Kefdrin, Lebac, Lebac Forte, Medicef, Mega-Cef, Megacin, Polycef, Procef, Procef, Procef forte, Rocef, Rocef Forte DS, Sefin, Sefin DS, Sefnin, Sefrad, Sefrad DS, Sefril, Sefril-DS, Sefro, Sefro-HS, Sephar, Sephar-DS, Septa, Sinaceph, SK-Cef, Sk-Cef DS, Supracef and Supracef-F, Torped, Ultrasef, Vecef, Vecef-DS, Velogen, Sinaceph, Velox
China: Cefradine, Cephradine, Kebili, Saifuding, Shen You, Taididing, Velosef, Xianyi, and Xindadelei
Colombia: Cefagram, Cefrakov, Cefranil , Cefrex, and Kliacef
Egypt: Cefadrin, Cefadrine, Cephradine, Cephraforte, Farcosef, Fortecef, Mepadrin, Ultracef, and Velosef
France: Dexef
Hong Kong: Cefradine and ChinaQualisef-250
Indonesia: Dynacef, Velodine, and Velodrom
Lebanon: Eskacef, Julphacef, and Velosef
Lithuania: Tafril
Myanmar: Sinaceph
Oman: Ceframed, Eskasef, Omadine, and Velocef
Pakistan: Abidine, Ada-Cef, Ag-cef, Aksosef, Amspor, Anasef, Antimic, Atcosef, Bactocef, Biocef, Biodine, Velora, Velosef
Peru: Abiocef, Cefradinal, Cefradur, Cefrid, Terbodina II, Velocef, Velomicin
Philippines: Altozef, Racep, Senadex, Solphride, Yudinef, Zefadin, Zefradil, and Zolicef
Poland: Tafril
Portugal: Cefalmin, Cefradur
South Africa: Cefril A
South Korea: Cefradine and Tricef
Taiwan: Cefadin, Cefamid, Cefin, Cekodin, Cephradine, Ceponin, Lacef, Licef-A, Lisacef, Lofadine, Recef, S-60, Sefree, Sephros, Topcef, Tydine, Unifradine, and U-Save
UK: Cefradune (Kent)
Vietnam: Eurosefro and Incef

Notes

^ Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefuroxime is generally effective in the eradication of streptococci from the nasopharynx

References

^ British National Formulary (45 ed.). London: British Medical Association. 2003.
^ Dolfini JE, Applegate HE, Bach G, Basch H, Bernstein J, Schwartz J, Weisenborn FL (February 1971). "A new class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine". Journal of Medicinal Chemistry. 14 (2): 117–9. doi:10.1021/jm00284a008. PMID 5544394.
^ U.S. patent 3,485,819
^ DE 1931722, Weisenborn, Frank L.; Dolfini, Joseph E. & Bach, Georges G. et al., "α-Amino-cyclohexadienyl-alkylen-penicilline und -cephalosporine, ihre Salze, und Verfahren zu ihrer Herstellung [Alpha-amino-cyclohexadienyl-alkylene-penicillins and cephalosporins, their salts, and processes for their preparation]", published 1970-01-08, assigned to E. R. Squibb & Sons Inc.
^ "Cefradine". Retrieved 5 May 2016.

[2] Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cefuroxime is generally effective in the eradication of streptococci from the nasopharynx

[1] British National Formulary (45 ed.). London: British Medical Association. 2003.

[3] Dolfini JE, Applegate HE, Bach G, Basch H, Bernstein J, Schwartz J, Weisenborn FL (February 1971). "A new class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine". Journal of Medicinal Chemistry. 14 (2): 117–9. doi:10.1021/jm00284a008. PMID 5544394.

[4] U.S. patent 3,485,819

[5] DE 1931722, Weisenborn, Frank L.; Dolfini, Joseph E. & Bach, Georges G. et al., "α-Amino-cyclohexadienyl-alkylen-penicilline und -cephalosporine, ihre Salze, und Verfahren zu ihrer Herstellung [Alpha-amino-cyclohexadienyl-alkylene-penicillins and cephalosporins, their salts, and processes for their preparation]", published 1970-01-08, assigned to E. R. Squibb & Sons Inc.

[6] "Cefradine". Retrieved 5 May 2016.

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