{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 470617807 | IUPAC_name = (3''R'',5''R'',6''R'',7''S'',8''R'',11''R'',12''S'',13''R'',14''S'',15''S'')-12-[(4-''O''-acetyl-2,6-dideoxy-3-''O''-methyl-α-<small>L</small>-''arabino''-hexopyranosyl)oxy]-14-{[2-''O''-acetyl-3,4,6-trideoxy-3-(dimethylamino)-β-<small>D</small>-''xylo''-hexopyranosyl]oxy}-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadec-6-yl acetate | image = troleandomycin.png | image_class = skin-invert-image
<!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|MTM|troleandomycin}} | MedlinePlus = a604026 | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 2751-09-9 | ATC_prefix = J01 | ATC_suffix = FA08 | PubChem = 5284630 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01361 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 45735 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4447675 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = C4DZ64560D | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = D01322 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 564085 | PDB_ligand = TAO
<!--Chemical data--> | C=41 | H=67 | N=1 | O=15 | 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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LQCLVBQBTUVCEQ-MCQAQMIOSA-N }}
'''Troleandomycin''' ('''TAO''' for short<ref name="Zeiger1980">{{cite journal | vauthors = Zeiger RS, Schatz M, Sperling W, Simon RA, Stevenson DD | title = Efficacy of troleandomycin in outpatients with severe, corticosteroid-dependent asthma | journal = The Journal of Allergy and Clinical Immunology | volume = 66 | issue = 6 | pages = 438–46 | date = December 1980 | pmid = 6968762 | doi = 10.1016/0091-6749(80)90003-2 | doi-access = free }}</ref>) 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|date=April 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.<ref name="Gurel2009">{{cite journal | vauthors = Gürel G, Blaha G, Steitz TA, Moore PB | title = Structures of triacetyloleandomycin and mycalamide A bind to the large ribosomal subunit of Haloarcula marismortui | journal = Antimicrobial Agents and Chemotherapy | volume = 53 | issue = 12 | pages = 5010–4 | date = December 2009 | pmid = 19738021 | pmc = 2786347 | doi = 10.1128/AAC.00817-09 }}</ref> Troleandomycin is a CYP3A4 inhibitor that may cause drug interactions.{{cn|date=January 2023}}
== References == {{Reflist}}
{{Macrolides, lincosamides and streptogramins}} {{Xenobiotic-sensing receptor modulators}}
Category:CYP3A4 inhibitors Category:Macrolide antibiotics Category:Epoxides Category:Spiro compounds Category:Acetate esters Category:Fourteen-membered rings Category:Dimethylamino compounds Category:Methoxy compounds
{{antibiotic-stub}}