Chemistry:Troleandomycin

Short description: Chemical compound

Troleandomycin

Clinical data
AHFS/Drugs.com	Multum Consumer Information
MedlinePlus	a604026
ATC code	J01FA08 (WHO)
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	2751-09-9 Y
PubChem CID	5284630
DrugBank	DB01361 Y
ChemSpider	4447675 Y
UNII	C4DZ64560D
KEGG	D01322 N
ChEBI	CHEBI:45735 N
ChEMBL	ChEMBL564085 N
PDB ligand	TAO (PDBe, RCSB PDB)
Chemical and physical data
Formula	C41H67NO15
Molar mass	813.979 g·mol−1
3D model (JSmol)	Interactive image
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)

Troleandomycin (TAO for short) 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. Troleandomycin is a CYP3A4 inhibitor that may cause drug interactions.