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Cefradine

From Wikipedia, the free encyclopedia
(Redirected fromCephradine)
Chemical compound
Pharmaceutical compound
Cefradine
Clinical data
Trade namesIntracef, Velocef
AHFS/Drugs.comInternational Drug Names
MedlinePlusa601206
Routes of
administration
Oral,IM,IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityWell absorbed
Protein binding<10%
MetabolismNil
Eliminationhalf-life0.9 hours
ExcretionRenal, unchanged
Identifiers
  • (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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.049.199Edit this at Wikidata
Chemical and physical data
FormulaC16H19N3O4S
Molar mass349.41 g·mol−1
3D model (JSmol)
Melting point140 to 142 °C (284 to 288 °F) (dec.)
  • 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=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 checkY
  • Key:RDLPVSKMFDYCOR-UEKVPHQBSA-N checkY
  (verify)

Cefradine (INN) orcephradine (BAN) is a first generationcephalosporinantibiotic.[1]

Indications

[edit]

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.[citation needed]

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

Synthesis

[edit]

Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected usingtert-butoxycarbonylazide and activated for amide formation via the mixed anhydride method using isobutylchloroformate to give3. Mixed anhydride3 reacted readily with 7-aminodesacetoxycephalosporanic acid to give, after deblocking, cephradine (5).

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

Production names

[edit]

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

  • Bangladesh 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 China: Cefradine, Cephradine, Kebili, Saifuding, Shen You, Taididing, Velosef, Xianyi, and Xindadelei
  • Colombia Colombia: Cefagram, Cefrakov, Cefranil , Cefrex, and Kliacef
  • Egypt Egypt: Cefadrin, Cefadrine, Cephradine, Cephraforte, Farcosef, Fortecef, Mepadrin, Ultracef, and Velosef
  • France France: Dexef
  • Hong Kong Hong Kong: Cefradine and ChinaQualisef-250
  • Indonesia Indonesia: Dynacef, Velodine, and Velodrom
  • Lebanon Lebanon: Eskacef, Julphacef, and Velosef
  • Lithuania Lithuania: Tafril
  • Myanmar Myanmar: Sinaceph
  • Oman Oman: Ceframed, Eskasef, Omadine, and Velocef
  • Pakistan Pakistan: Abidine, Ada-Cef, Ag-cef, Aksosef, Amspor, Anasef, Antimic, Atcosef, Bactocef, Biocef, Biodine, Velora, Velosef
  • Peru Peru: Abiocef, Cefradinal, Cefradur, Cefrid, Terbodina II, Velocef, Velomicin
  • Philippines Philippines: Altozef, Racep, Senadex, Solphride, Yudinef, Zefadin, Zefradil, and Zolicef
  • Poland Poland: Tafril
  • Portugal Portugal: Cefalmin, Cefradur
  • South Africa South Africa: Cefril A
  • South Korea South Korea: Cefradine and Tricef
  • Taiwan Taiwan: Cefadin, Cefamid, Cefin, Cekodin, Cephradine, Ceponin, Lacef, Licef-A, Lisacef, Lofadine, Recef, S-60, Sefree, Sephros, Topcef, Tydine, Unifradine, and U-Save
  • United Kingdom UK: Cefradune (Kent)
  • Vietnam Vietnam: Eurosefro and Incef

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

References

[edit]
  1. ^British National Formulary (45 ed.). London: British Medical Association. 2003.
  2. ^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.
  3. ^U.S. patent 3,485,819
  4. ^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 toE. R. Squibb & Sons Inc. 
  5. ^"Cefradine". Retrieved5 May 2016.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
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Combinations
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  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
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CARTooltip Constitutive androstane receptor
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Retrieved from "https://en.wikipedia.org/w/index.php?title=Cefradine&oldid=1179953645"
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