Troleandomycin

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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--14-{oxy}-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspirohexadec-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)
CompTox Dashboard (EPA)	DTXSID2023721
ECHA InfoCard	100.018.539
Chemical and physical data
Formula	C41H67NO15
Molar mass	813.979 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O4(N(C)C)C(O4O3((O1O((OC(=O)C)(OC)C1)C)(C(=O)O(C)(C)(OC(=O)C)(C(=O)2(OC2)C3C)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.^{[citation needed]}

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.^{[citation needed]}

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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