Cefradine

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Cefradine
Cefradine.svg
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
Routes of
administration
Oral, IM, IV
Legal status
Legal status
  • ℞ (Prescription only)
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 YesY
ATC code J01DB09 (WHO)
PubChem CID 38103
IUPHAR/BPS 4830
DrugBank DB01333 YesY
ChemSpider 34933 YesY
UNII 9YA6SX5S4D YesY
KEGG D00264 YesY
ChEBI CHEBI:3547 YesY
ChEMBL CHEMBL1604 YesY
Chemical data
Formula C16H19N3O4S
Molar mass 349.406 g/mol
  (verify)

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

Indications[edit]

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

Formulations[edit]

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.

Production Names[edit]

The antibiotic is produced under a wide number of brand names across the world.[2]

  • Bangladesh: Ancef (Unimed & Unihealth), Ancef forte (Unimed & Unihealth), Aphrin (Apex), Avlosef (ACI), Cefadin (Ziska), Cephadin (Square); Cephran and Cephran-DS (Opsonin), Cusef and Cusef DS (Delta), Dicef (Drug International), Dicef forte (Drug International), Dolocef (Techno), Efrad (Edruc), Extracef (Aristopharma), Extracef-DS (Aristopharma), Intracef (Beximco), Kefdrin (GlaxoSmithKline), Lebac (Square), Lebac Forte (Square), Medicef (Medicon), Mega-Cef (Hudson), Megacin (Novartis), Polycef (Renata), Procef (Incepta), Procef (Cefradine and Arginine) (Incepta), Procef forte (Incepta), Rocef and Rocef Forte DS (Healthcare), Sefin and Sefin DS (Orion), Sefnin (Monico), Sefrad and Sefrad DS (Sanofi-Aventis), Sefril and Sefril-DS (Acme), Sefro and Sefro-HS (Navana), Sephar and Sephar-DS (RAK), Septa (Doctor's Chemical Works), Sinaceph (Ibn Sina), SK-Cef and Sk-Cef DS (Eskayef), Supracef and Supracef-F (Bio-Pharma), Torped (Orion), Ultrasef (Jayson), Vecef and Vecef-DS (Asiatic Lab) and Velogen (General Pharma),
  • China: Cefradine (Likang, Linheng Pharmaceutical, Livzon Zhuhai, Siyao Pharmaceuticals, WZ Pharm, China and Xinhua), Cephradine (New Asiatic Pharm and Sine Pharm), Kebili (Baiyunshan), Saifuding (The United Laboratories Ltd), Shen You (Shyndec), Taididing (Gosun), Velosef (Bristol-Myers Squibb), Xianyi (Dawnrays) and Xindadelei (Xincat)
  • Columbia: Cefagram (Coaspharma), Cefrakov (Blaskov), Cefranil (Biotoscana), Cefrex (Labinco) and Kliacef (Bioquifar)
  • Egypt: Cefadrin and Cefadrine (T3A), Cephradine (Eipico), Cephraforte (Sina), Farcosef (PBI)Fortecef (Meivo), Mepadrin (Mepaco), Ultracef (Misr) and Velosef (GlaxoSmithKline)
  • France: Dexef (CSP, France)
  • Hong Kong: Cefradine (Bright Future) and ChinaQualisef-250 (Quality Pharm)
  • Indonesia: Dynacef (Dexa Medica), Velodine (Soho) and Velodrom (Ethica Industri Farmasi)
  • Lebanon: Eskacef (Julphar, Lebanon), Julphacef (Julphar, Lebanon) and Velosef (Squibb Aebe)
  • Lithuania: Tafril (Warszawskie Zaklady Farmaceutyczne Polfa)
  • Myanmar: Sinaceph (IBN)
  • Oman: Ceframed (Khimji Ramdas), Eskasef (Julphar), Omadine (NPI) and Velocef (Abeefe Bristol-Myers Squibb)
  • Pakistan: Abidine (Alliance), Ada-Cef (Adamjee), Ag-cef (Saydon), Aksosef (Akson), Amspor (Wilshire), Anasef (Mass Pharma), Antimic (Danas), Atcosef (Atco), Bactocef (Swiss), Biocef (Searle)
  • Peru: Abiocef (Infermed), Cefradinal (Terbol, Peru), Cefradur (Atral), Cefrid (Infarmasa), Terbodina II (Terbol), Velocef (Abeefe Bristol-Myers Squibb), Velomicin (Siegfried)
  • The Philippines: Altozef (Altomed), Racep (Samjin), Senadex (Nutramedica), Solphride (Lloyd),Yudinef (Biolink, Philippines), Zefadin (Singapore Pharmawealth Lifesciences), Zefradil (NCPC Hebei Huamin Pharma) and Zolicef (Harbin)
  • Poland: Tafril (Polfa Tarchomin)
  • Portugal: Cefalmin (Labesfal), Cefradur (Atral),
  • South Africa: Cefril A (Bristol-Myers Squibb)
  • South Korea: Cefradine (Hanmi) and Tricef (Kukj)
  • Taiwan: Cefadin (Standard), Cefamid (Gentle), Cefin (Tai Yu) Cekodin (Swiss Pharm), Cephradine (Kojar and Root), Ceponin (Chi Sheng), Lacef (Tai Yu), Licef-A and Lisacef (Taiwan Biotech), Lofadine (Gentle), Recef (Purzer), S-60 (Yung Shin), Sefree (Panbiotic), Sephros (Yung Shin), Topcef (Gentle), Tydine (TTY Biopharm), Unifradine (Union) and U-Save (U-Liang)
  • UK: Cefradune (Kent)
  • Vietnam: Eurosefro (Navana Pharmaceuticals) and Incef (Inbionet)

Cefradine is known as Cefradina in Portuguse 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.

Synthesis[edit]

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:[3] 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 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).

See also[edit]

Notes[edit]

  1. ^ 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
  2. ^ Among beta-lactam antibiotics, ampicillin is the drug of choice for enterococcal urinary tract (E. faecalis) infection.

References[edit]

  1. ^ British National Formulary (45 ed.). London: British Medical Association. 2003. 
  2. ^ {cite web|url=http://www.drugs.com/international/cefradine.html%7Ctitle=Cefradine%7Caccess-date=5 May 2016}
  3. ^ Dolfini, Joseph E.; Applegate, Harold E.; Bach, Georges; Basch, Harold; Bernstein, Jack; Schwartz, Joseph; Weisenborn, Frank L. (1971). "New class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine". Journal of Medicinal Chemistry 14 (2): 117. doi:10.1021/jm00284a008. PMID 5544394.