Sisomicin

Synonym(s): Sisomycin  |  rickamicin  |  antibiotic 6640

Class: Aminoglycoside

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-positive and Gram-negative bacteria
Description:	Micromonospora natural product. Used for topical application
Institute where first reported:	Merck Sharp & Dohme LLC
Year first mentioned:	1950
Highest developmental phase:	Phase 4 (NCT00202891)
Development status:	Inactive
Reason Dropped:	Withdrawn during clinical trial

Chemical structure(s):
Canonical 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](CC=C(CN)O3)N)N)N)O
Isomeric 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](CC=C(O3)CN)N)N)N)O
InChI:	InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
InChI Key:	URWAJWIAIPFPJE-YFMIWBNJSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/36119

External links:
Guide to Pharmacology:	sisomicin
Main Source:	https://www.jstage.jst.go.jp/article/antibiotics1968/23/11/23_11_551/_article
Citations:	https://pubmed.ncbi.nlm.nih.gov/34905092/ https://pubmed.ncbi.nlm.nih.gov/6994206/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC429460/