Troleandomycin

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
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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 checkY
  • Key:LQCLVBQBTUVCEQ-MCQAQMIOSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.

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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