Troleandomycin

• CAT Number: I037550
• CAS Number: 2751-09-9
• Molecular Formula: C41H67NO15
• Molecular Weight: 813.98
• Purity: 98%
• Synonyms: Troleandomycin, AI3-50166, Aovine, Cyclamycin, Matromycin T, Micotil, Oleandocetine, Oleandomycin triacetate, Oleandomycin triacetyl ester, Triacetyloleandomycin, Triocetin, Triolan, WY 651; Wytrion; NSC 108166; NSC-108166; NSC108166
• Target: Anti-infection
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (2S,3R,4S,6R)-2-(((3R,5R,6S,7S,8R,11R,12S,13R,14S,15S)-6-acetoxy-12-(((2R,4S,5S,6S)-5-acetoxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadecan-14-yl)oxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate
• 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
• InChIKey: LQCLVBQBTUVCEQ-QTFUVMRISA-N
• SMILES: CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3OC(=O)C)N(C)C)[C@@H](C)C[C@@]4(CO4)C(=O)[C@H](C)[C@@H](OC(=O)C)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1OC(=O)C

Troleandomycin (Cat.No:I037550) is a macrolide antibiotic with antimicrobial properties. It was previously used to treat respiratory tract infections, including pneumonia and bronchitis. However, due to potential liver toxicity and drug interactions, its clinical use has been limited. Troleandomycin is now primarily used as a research tool in studies related to drug metabolism and interactions.

Reference

1: Evans DJ, Cullinan P, Geddes DM. Troleandomycin as an oral corticosteroid steroid sparing agent in stable asthma. Cochrane Database Syst Rev. 2001;(2):CD002987. Review. PubMed PMID: 11406054.
2: Yamazaki H, Hiroki S, Urano T, Inoue K, Shimada T. Effects of roxithromycin, erythromycin and troleandomycin on their N-demethylation by rat and human cytochrome P450 enzymes. Xenobiotica. 1996 Nov;26(11):1143-53. PubMed PMID: 8948090.
3: Pessayre D, Tinel M, Larrey D, Cobert B, Funck-Brentano C, Babany G. Inactivation of cytochrome P-450 by a troleandomycin metabolite. Protective role of glutathione. J Pharmacol Exp Ther. 1983 Mar;224(3):685-91. PubMed PMID: 6600790.
4: Weinberger M, Hudgel D, Spector S, Chidsey C. Inhibition of theophylline clearance by troleandomycin. J Allergy Clin Immunol. 1977 Mar;59(3):228-31. PubMed PMID: 300083.