isepamicin
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 376143372
| IUPAC_name = (2S)-3-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-D-glucopyranosyl)oxy]-2-{[3-deoxy-4-C-methyl-3-(methylamino)-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl)-2-hydroxypropanamide
| image = Isepamicin.svg
| tradename =
| Drugs.com = {{drugs.com|international|isepamicin}}
| pregnancy_AU =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 58152-03-7
| ATC_prefix = J01
| ATC_suffix = GB11
| PubChem = 3037209
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = G7K224460P
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 272080
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2301019
| C=22 | H=43 | N=5 | O=12
| smiles = C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UDIIBEDMEYAVNG-ZKFPOVNWSA-N
| synonyms = Isepamycin
(2S)-3-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylaminooxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide
}}
Isepamicin (isepamycin) is an aminoglycoside antibiotic.
It was patented in 1973 and approved for medical use in 1988.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=508 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA508 |language=en}} It has been identified by the World Health Organization as a Critically Important Antimicrobial for human use.{{cite web | publisher = World Health Organization | date = 2012 | title = Critically important antimicrobials for human medicine.| url = http://apps.who.int/iris/bitstream/10665/77376/1/9789241504485_eng.pdf }}
Synthesis
Isepamicin can be synthesized by derivatization of gentamicin B (1) with benzyl N-[(2S)-3-(2,5-dioxopyrrolidin-1-yl)-2-hydroxy-3-oxopropyl]carbamate (2), followed by deprotection.Serradell, MN; Blancafort, P.; Roberts, PJ; Castaer, J.; SCH-21420. Drugs Fut 1979, 4, 7, 525.John J. Wright, {{US patent|4029882}} (1977 to Merck Sharp and Dohme Corp).[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0060 Thieme][https://www.chemdrug.com/article/8/3284/16419317.html ChemDrug]