Compound ID | 1851

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Sisomicin

Synonym(s): Sisomycin  |  rickamicin  |  antibiotic 6640

Class: Aminoglycoside

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 30S ribosomal subunit
Target Pathogen: 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 development stage: Approved; Phase 4 (NCT00202891)
Development status: Withdrawn
Reason dropped: No interest in pursuing clinical trial
Chemical structure(s):
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Molecular weight: 447.53
Iso. 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 Key: URWAJWIAIPFPJE-YFMIWBNJSA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/36119
Guide to Pharmacology: sisomicin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/34905092/
  • https://pubmed.ncbi.nlm.nih.gov/6994206/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC429460/
  • https://www.jstage.jst.go.jp/article/antibiotics1968/23/11/23_11_551/_article

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