Cefsulodin: Difference between revisions

(39 intermediate revisions by 31 users not shown)

Line 1:

{{Drugbox

| ~~Watchedfields~~ = changed

| Verifiedfields = changed

| verifiedrevid = ~~444592291~~

| verifiedrevid = 447923576

| IUPAC_name = 4-(aminocarbonyl)-1-[((6''R'',7''R'')-2-carboxy-8-oxo-7-{[phenyl(sulfo)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]pyridinium

| image = cefsulodin.png

Line 16:

Line 18:

| legal_US =

| legal_status =

| routes_of_administration =

Line 23:

Line 25:

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = ~~52152~~-93-9

| CAS_number = 62587-73-9

| ATC_prefix = J01

| ATC_suffix = DD03

Line 38:

Line 41:

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

| KEGG = D02005

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1617285

| index2_label = Sodium salt

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 52152-93-9

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 2D087186PY

| C=22 | H=21 | N=4 | O=8 | S=2 | charge = +

| molecular_weight = 533.556 g/mol

| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(c3ccccc3)S(=O)(=O)O)C[n+]4ccc(C(=O)N)cc4)C([O-])=O

| InChI = 1/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17?,21-/m1/s1

| InChIKey = SYLKGLMBLAAGSC-IKZMBGHXBW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17?,21-/m1/s1

Line 51:

Line 58:

}}

'''Cefsulodin''' is a third-generation [[cephalosporin]] antibiotic that is active against ''[[Pseudomonas aeruginosa]]'' and was discovered by [[Takeda Pharmaceutical Company]] in 1977.<ref name="racgp">{{cite web |url = https://www.toku-e.com/Upload/Products/Article/20110323002554.pdf |title = TOKU-E Technical Application Sheet |archive-url=https://web.archive.org/web/20110927174740/https://www.toku-e.com/Upload/Products/Article/20110323002554.pdf |archive-date=27 September 2011 |url-status=dead}}</ref><ref name="Smith_1084">{{cite journal | vauthors = Smith BR | title = Cefsulodin and ceftazidime, two antipseudomonal cephalosporins | journal = Clinical Pharmacy | volume = 3 | issue = 4 | pages = 373–85 | date = 1984 | pmid = 6380902 | doi = | url = }}</ref><ref name="Neu_1984">{{cite journal | vauthors = Neu HC, Scully BE | title = Activity of cefsulodin and other agents against Pseudomonas aeruginosa | journal = Reviews of Infectious Diseases | volume = 6 | issue = Suppl 3| pages = S667–77 | date = 1984 | pmid = 6443768 | doi = 10.1093/clinids/6.supplement_3.s667 }}</ref><ref name="Wright_1986">{{cite journal | vauthors = Wright DB | title = Cefsulodin | journal = Drug Intelligence & Clinical Pharmacy | volume = 20 | issue = 11 | pages = 845–9 | date = November 1986 | pmid = 3536385 | doi = 10.1177/106002808602001104 | s2cid = 243377437 }}</ref>

'''Cefsulodin''' is a third generation [[cephalosporin]] antibiotic that has very specific activity against ''[[Pseudomonas aeruginosa]]''. It has no significant activity against other Gram-negative bacteria and very limited activity against Gram-positive bacteria and anaerobic bacteria. Cefsulodin was first synthesized and patented by the [[Takeda Pharmaceutical Company]] in 1977. In 2002, Takeda stopped production of Cefsulodin. Many years of low-stability cefsulodin production has led to a widespread reduction of laboratory and research usages. Current attempts (i.e. [[IDEXX Laboratories]]) of increasing purity and stability of cefsulodin center around recrystallization. Typically the process entails the following: Cefsulodin is dissolved in an organic solvent, sodium, water or any mixture thereof, then subsequently recrystallized through separation of the unwanted fraction. Recently, [[TOKU-E]] has found that the main cause of cefsulodin instability stems from one key impurity in [[7-ACA]] (7-aminocephalosporanic acid- a raw material used in the synthesis of cefsulodin). In order to produce high-purity, high-stability cefsulodin, TOKU-E uses industrial HPLC to remove significant quantities of this impurity in 7-ACA and thus produces ultra-pure, ultra-stable, and ultra potent cefsulodin.<ref name="racgp">[http://www.toku-e.com/Upload/Products/Article/20110323002554.pdf], TOKU-E Technical Application Sheet.</ref>

[[TAP Pharmaceuticals]] had a new drug application on file with FDA for cefsulodin under the brand name Cefonomil as of 1985.<ref>{{cite news|title=Lupron Is First Abbott-Takeda Product to Reach U.S. Market|url=https://pink.pharmamedtechbi.com/PS008170/LUPRON-IS-FIRST-ABBOTTTAKEDA-PRODUCT-TO-REACH-US-MARKET-FDA-APPROVES-SYNTHETIC-LHRH-ANALOG-WAS-TREATED-AS-1A-BREAKTHROUGH-FOR-PROSTATE-CANCER|work=Pink Sheet|date=15 April 1985}}</ref>

Cefsulodin is most commonly used in cefsulodin-irgasan-novobiocin agar to select for ''Yersinia'' microorganisms.<ref>{{cite web|title=BAM Media M35: Cefsulodin-Irgasan Novobiocin Agar or Yersinia Selective Agar|website=[[Food and Drug Administration]]|url=https://www.fda.gov/Food/ScienceResearch/LaboratoryMethods/BacteriologicalAnalyticalManualBAM/ucm064575.htm|access-date=2 September 2012}}</ref> This agar is most often used in water and beverage testing.{{cn|date=March 2023}}

== Susceptibility data ==

The following represents MIC susceptibility data for various ''P. aeruginosa'' strains:<ref>{{Cite web|url=http://antibiotics.toku-e.com/antimicrobial_474.html|title = Cefsulodin | the Antimicrobial Index Knowledgebase - TOKU-E}}</ref>

* ''Pseudomonas aeruginosa'' PA13 (resistant strain): 32 μg/ml

* ''Pseudomonas aeruginosa'' (wild-type, susceptible): 4 - 8 μg/ml

== General use ==

Cefuslodin is most commonly used in CIN (cefsulodin-Irgasan-novobiocin) agar to select for all microorganisms (most importantly E. Coli) except Yersinia. This agar is most often used in water and beverage testing.

==References==

Line 64:

Line 76:

[[Category:Cephalosporin antibiotics]]

[[Category:Isonicotinamides]]

[[Category:Drugs developed by Takeda Pharmaceutical Company]]

[[fr:~~Cefsulodine~~]]

[[Category:Sulfonates]]

[[zh:头孢磺啶]]