Troleandomycin

Troleandomycin (TAO for short[1]) is a macrolide antibiotic. It was sold in Italy (branded Triocetin) and Turkey (branded Tekmisin). It is no longer sold in Italy as of 2018.

Troleandomycin
Clinical data
AHFS/Drugs.comMultum Consumer Information
MedlinePlusa604026
ATC code
Identifiers
IUPAC name
  • (3R,5R,6R,7S,8R,11R,12S,13R,14S,15S)-12-[(4-O-acetyl-2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-14-{[2-O-acetyl-3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadec-6-yl acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.018.539
Chemical and physical data
FormulaC41H67NO15
Molar mass813.979 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O[C@@H]4[C@@H](N(C)C)C[C@H](O[C@H]4O[C@@H]3[C@H]([C@H](O[C@@H]1O[C@H]([C@H](OC(=O)C)[C@@H](OC)C1)C)[C@H](C(=O)O[C@H](C)[C@H](C)[C@H](OC(=O)C)[C@H](C(=O)[C@]2(OC2)C[C@@H]3C)C)C)C)C)C
InChI
  • InChI=1S/C41H67NO15/c1-19-17-41(18-49-41)38(46)23(5)34(53-27(9)43)21(3)25(7)52-39(47)24(6)35(56-32-16-31(48-14)36(26(8)51-32)54-28(10)44)22(4)33(19)57-40-37(55-29(11)45)30(42(12)13)15-20(2)50-40/h19-26,30-37,40H,15-18H2,1-14H3/t19-,20+,21-,22+,23+,24+,25+,26-,30-,31-,32-,33-,34-,35-,36-,37+,40-,41-/m0/s1 Y
  • Key:LQCLVBQBTUVCEQ-MCQAQMIOSA-N Y
 NY (what is this?)  (verify)

The drug's mode of action is to bind to the ribosome, specifically in the tunnel through which the newly formed peptide egresses, thereby halting protein synthesis.[2] Troleandomycin is a CYP3A4 inhibitor that may cause drug interactions.

References
  1. Zeiger RS, Schatz M, Sperling W, Simon RA, Stevenson DD (December 1980). "Efficacy of troleandomycin in outpatients with severe, corticosteroid-dependent asthma". The Journal of Allergy and Clinical Immunology. 66 (6): 438–46. doi:10.1016/0091-6749(80)90003-2. PMID 6968762.
  2. Gürel G, Blaha G, Steitz TA, Moore PB (December 2009). "Structures of triacetyloleandomycin and mycalamide A bind to the large ribosomal subunit of Haloarcula marismortui". Antimicrobial Agents and Chemotherapy. 53 (12): 5010–4. doi:10.1128/AAC.00817-09. PMC 2786347. PMID 19738021.
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