Cefradine: Difference between revisions

{{short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 443510316

| IUPAC_name = (6''R'',7''R'')-7-{[(2''R'')-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-->

| tradename = Intracef, Velocef

| Drugs.com = {{drugs.com|international|cefradine}}

| MedlinePlus = a601206

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral, [[Intramuscular injection|IM]], [[Intravenous therapy|IV]]

<!--Pharmacokinetic data-->

| bioavailability = Well absorbed

| protein_bound = <10%

| metabolism = Nil

| elimination_half-life = 0.9 hours

| excretion = [[Kidney|Renal]], unchanged

<!--Identifiers-->

| IUPHAR_ligand = 4830

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 38821-53-3

| ATC_prefix = J01

| ATC_suffix = DB09

| PubChem = 38103

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01333

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00264

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3547

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1604

<!--Chemical data-->

| C=16 | H=19 | N=3 | O=4 | S=1

| melting_point = 140

| melting_high = 142

| melting_notes = (dec.)

'''Cefradine''' ([[International Nonproprietary Name|INN]]) or '''cephradine''' ([[British Approved Name|BAN]]) is a first generation [[cephalosporin]] [[antibiotic]].<ref>{{cite book|title=British National Formulary|date=2003|publisher=British Medical Association|location=London|edition=45}}</ref>

== Indications ==

* Respiratory tract infections (such as [[tonsillitis]], [[pharyngitis]], and [[lobar pneumonia]]) caused by group A beta-hemolytic [[streptococci]] and [[Streptococcus pneumoniae|''S. pneumoniae'']] (formerly ''D. pneumonia'').<ref group=note>[[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</ref>

* Otitis media caused by group A beta-hemolytic streptococci, ''S. pneumoniae'', [[Haemophilus influenzae|''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 [[Escherichia coli|''E. coli'']], [[Proteus mirabilis|''P. mirabilis'']] and ''[[Klebsiella]]'' species.

== Formulations ==

Cefradine is distributed in the form of capsules containing 250&nbsp;mg or 500&nbsp;mg, as a syrup containing 250&nbsp;mg/5 ml, or in vials for injection containing 500&nbsp;mg or 1&nbsp;g.{{cn|date=March 2023}}

It is not approved by the FDA for use in the United States.{{cn|date=March 2023}}

== 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''').

[[File:Cefradine synthesis.svg|thumb|center|700px|Cefradin synthesis:<ref>{{cite journal | vauthors = Dolfini JE, Applegate HE, Bach G, Basch H, Bernstein J, Schwartz J, Weisenborn FL | title = A new class of semisynthetic penicillins and cephalosporins derived from D-2-(1,4-cyclohexadienyl)glycine | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 2 | pages = 117–9 | date = February 1971 | pmid = 5544394 | doi = 10.1021/jm00284a008 }}</ref><ref>{{US patent|3485819}}</ref><ref>{{cite patent|country=DE|number=1931722|title=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]

|pubdate=1970-01-08

|assign=[[Bristol Myers Squibb|E. R. Squibb & Sons Inc.]]

|inventor1-last=Weisenborn |inventor1-first=Frank L.

|inventor2-last=Dolfini |inventor2-first=Joseph E.

|inventor3-last=Bach |inventor3-first=Georges G.

|inventor4-last=Bernstein |inventor4-first=Jack

}}</ref>]]{{clear-left}}

== Production names ==

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>

* {{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

* {{flagicon|China}} China: Cefradine, Cephradine, Kebili, Saifuding, Shen You, Taididing, Velosef, Xianyi, and Xindadelei

* {{flagicon|Colombia}} Colombia: Cefagram, Cefrakov, Cefranil , Cefrex, and Kliacef

* {{flagicon|Egypt}} Egypt: Cefadrin, Cefadrine, Cephradine, Cephraforte, Farcosef, Fortecef, Mepadrin, Ultracef, and Velosef

* {{flagicon|France}} France: Dexef

* {{flagicon|Hong Kong}} Hong Kong: Cefradine and ChinaQualisef-250

* {{flagicon|Indonesia}} Indonesia: Dynacef, Velodine, and Velodrom

* {{flagicon|Lebanon}} Lebanon: Eskacef, Julphacef, and Velosef

* {{flagicon|Lithuania}} Lithuania: Tafril

* {{flagicon|Myanmar}} Myanmar: Sinaceph

* {{flagicon|Oman}} Oman: Ceframed, Eskasef, Omadine, and Velocef

* {{flagicon|Pakistan}} Pakistan: Abidine, Ada-Cef, Ag-cef, Aksosef, Amspor, Anasef, Antimic, Atcosef, Bactocef, Biocef, Biodine, Velora, Velosef

* {{flagicon|Peru}} Peru: Abiocef, Cefradinal, Cefradur, Cefrid, Terbodina II, Velocef, Velomicin

* {{flagicon|Philippines}} Philippines: Altozef, Racep, Senadex, Solphride, Yudinef, Zefadin, Zefradil, and Zolicef

* {{flagicon|Poland}} Poland: Tafril

* {{flagicon|Portugal}} Portugal: Cefalmin, Cefradur

* {{flagicon|South Africa}} South Africa: Cefril A

* {{flagicon|South Korea}} South Korea: Cefradine and Tricef

* {{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

* {{flagicon|United Kingdom}} UK: Cefradune (Kent)

* {{flagicon|Vietnam}} Vietnam: Eurosefro and Incef

== See also ==

* [[Cephapirin]]

* [[Cephacetrile]]

* [[Cefamandole]]

* [[Ampicillin]] (Has the same chemical formula)

== Notes ==

{{reflist|group=note}}

== References ==

{{reflist}}

{{Xenobiotic-sensing receptor modulators}}