| Revision as of 14:08, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit |
Latest revision as of 14:49, 13 October 2023 edit undo103.218.24.129 (talk) →Production names |
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{{short description|Chemical compound}} |
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{{drugbox | verifiedrevid = 411550719 |
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{{Drugbox |
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| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-methyl-8-oxo-5-thia-<br>1-azabicyclooct-2-ene-2-carboxylic acid |
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| verifiedrevid = 443510316 |
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| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-methyl-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid |
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| image = Cefradine.svg |
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| image = Cefradine.svg |
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<!--Clinical data--> |
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| tradename = Intracef, Velocef |
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| Drugs.com = {{drugs.com|international|cefradine}} |
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| MedlinePlus = a601206 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_status = Rx-only |
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| routes_of_administration = Oral, ], ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = Well absorbed |
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| protein_bound = <10% |
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| metabolism = Nil |
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| elimination_half-life = 0.9 hours |
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| excretion = ], unchanged |
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<!--Identifiers--> |
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| IUPHAR_ligand = 4830 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 38821-53-3 |
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| ATC_prefix = J01 |
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| ATC_suffix = DB09 |
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| PubChem = 38103 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01333 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 34933 |
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| ChemSpiderID = 34933 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9YA6SX5S4D |
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| UNII = 9YA6SX5S4D |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/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 |
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| KEGG = D00264 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 3547 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1604 |
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<!--Chemical data--> |
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| C=16 | H=19 | N=3 | O=4 | S=1 |
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| smiles = O=C2N1/C(=C(\CS12NC(=O)(C/3=C/C\C=C/C\3)N)C)C(=O)O |
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| smiles = O=C2N1/C(=C(\CS12NC(=O)(C/3=C/C\C=C/C\3)N)C)C(=O)O |
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| InChIKey = RDLPVSKMFDYCOR-UEKVPHQBBU |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RDLPVSKMFDYCOR-UEKVPHQBSA-N |
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| StdInChIKey = RDLPVSKMFDYCOR-UEKVPHQBSA-N |
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| melting_point = 140 |
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| CAS_number = 38821-53-3 |
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| ATC_prefix = J01 |
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| melting_high = 142 |
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| melting_notes = (dec.) |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1604 |
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| ATC_suffix = DB09 |
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| ChEBI = 3547 |
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| PubChem = 38103 |
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| DrugBank = DB01333 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00264 |
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| C = 16 | H = 19 | N = 3 | O = 4 | S = 1 |
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| molecular_weight = 349.406 g/mol |
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| bioavailability = Well absorbed |
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| protein_bound = <10% |
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| metabolism = Nil |
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| elimination_half-life = 0.9 hours |
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| excretion = ], unchanged |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_status = Rx-only |
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| routes_of_administration = Oral, ], ] |
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}} |
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}} |
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'''Cefradine''' (]) (formerly '''cephradine''' ]) is a first generation ] ]. |
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'''Cefradine''' (]) or '''cephradine''' (]) is a first generation ] ].<ref>{{cite book|title=British National Formulary|date=2003|publisher=British Medical Association|location=London|edition=45}}</ref> |
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==Indications== |
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== Indications == |
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* Respiratory tract infections (such as ], ], and ]) caused by group A beta-hemolytic ] and ] (formerly ''D. pneumonia'').<ref group=note>] is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. ] is generally effective in the eradication of streptococci from the nasopharynx</ref> |
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It has similar spectrum of activity to ]. |
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* Otitis media caused by group A beta-hemolytic streptococci, ''S. pneumoniae'', ], and ]. |
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* Skin and skin structure infections caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. |
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* Urinary tract infections, including prostatitis, caused by ], ] and '']'' species. |
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==Formulations== |
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== Formulations == |
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Capsules containing 250 mg or 500 mg, Syrup containing 250 mg/5 ml, or vials for injection containing 500 mg or 1 g. |
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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.{{cn|date=March 2023}} |
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It is not approved by the FDA for use in the United States.{{cn|date=March 2023}} |
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==References== |
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* ] ''45'' March 2003 |
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== Synthesis == |
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] of D-α-] 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'''). |
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|pubdate=1970-01-08 |
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|assign=] |
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|inventor1-last=Weisenborn |inventor1-first=Frank L. |
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|inventor2-last=Dolfini |inventor2-first=Joseph E. |
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|inventor3-last=Bach |inventor3-first=Georges G. |
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|inventor4-last=Bernstein |inventor4-first=Jack |
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}}</ref>]]{{clear-left}} |
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== Production names == |
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The antibiotic is produced under many brand names across the world.<ref>{{cite web|url=https://www.drugs.com/international/cefradine.html|title=Cefradine|access-date=5 May 2016}}</ref> |
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* {{flagicon|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 |
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* {{flagicon|China}} China: Cefradine, Cephradine, Kebili, Saifuding, Shen You, Taididing, Velosef, Xianyi, and Xindadelei |
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* {{flagicon|Colombia}} Colombia: Cefagram, Cefrakov, Cefranil , Cefrex, and Kliacef |
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* {{flagicon|Egypt}} Egypt: Cefadrin, Cefadrine, Cephradine, Cephraforte, Farcosef, Fortecef, Mepadrin, Ultracef, and Velosef |
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* {{flagicon|France}} France: Dexef |
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* {{flagicon|Hong Kong}} Hong Kong: Cefradine and ChinaQualisef-250 |
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* {{flagicon|Indonesia}} Indonesia: Dynacef, Velodine, and Velodrom |
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* {{flagicon|Lebanon}} Lebanon: Eskacef, Julphacef, and Velosef |
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* {{flagicon|Lithuania}} Lithuania: Tafril |
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* {{flagicon|Myanmar}} Myanmar: Sinaceph |
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* {{flagicon|Oman}} Oman: Ceframed, Eskasef, Omadine, and Velocef |
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* {{flagicon|Pakistan}} Pakistan: Abidine, Ada-Cef, Ag-cef, Aksosef, Amspor, Anasef, Antimic, Atcosef, Bactocef, Biocef, Biodine, Velora, Velosef |
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* {{flagicon|Peru}} Peru: Abiocef, Cefradinal, Cefradur, Cefrid, Terbodina II, Velocef, Velomicin |
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* {{flagicon|Philippines}} Philippines: Altozef, Racep, Senadex, Solphride, Yudinef, Zefadin, Zefradil, and Zolicef |
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* {{flagicon|Poland}} Poland: Tafril |
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* {{flagicon|Portugal}} Portugal: Cefalmin, Cefradur |
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* {{flagicon|South Africa}} South Africa: Cefril A |
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* {{flagicon|South Korea}} South Korea: Cefradine and Tricef |
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* {{flagicon|Taiwan}} Taiwan: Cefadin, Cefamid, Cefin, Cekodin, Cephradine, Ceponin, Lacef, Licef-A, Lisacef, Lofadine, Recef, S-60, Sefree, Sephros, Topcef, Tydine, Unifradine, and U-Save |
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* {{flagicon|United Kingdom}} UK: Cefradune (Kent) |
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* {{flagicon|Vietnam}} Vietnam: Eurosefro and Incef |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] (Has the same chemical formula) |
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== Notes == |
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{{reflist|group=note}} |
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== References == |
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{{reflist}} |
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{{CephalosporinAntiBiotics}} |
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{{CephalosporinAntiBiotics}} |
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{{Xenobiotic-sensing receptor modulators}} |
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] |
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] |
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] |
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] |
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{{antibiotic-stub}} |
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] |
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] |
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] |
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] |
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] |
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] |
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