Troleandomycin

Chemical data

Formula

C41H67NO15

Molecular weight

814 g/mol

IUPAC name

[(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate

SMILES

C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C

InChIKey

LQCLVBQBTUVCEQ-QTFUVMRISA-N

XLogP

4.3

Polar surface area

184 Ų

H-bond donors

0

H-bond acceptors

16

Formal charge

0

via PubChem

Drug data · ChEMBL

Max clinical phase

Approved

Molecule type

Small molecule

First approval

1969

Admin. routes

oral

Indications

osteomyelitis, bacterial disease

via ChEMBL · EBI

• Troleandomycin as an oral corticosteroid steroid sparing agent in stable asthma.The Cochrane database of systematic reviews · 2001
• Hepatotoxicity of erythromycin.The Journal of infectious diseases · 1969
• Liquid chromatography of troleandomycin.Journal of chromatography. A · 2001
• Troleandomycin in the treatment of difficult asthma.The Journal of allergy and clinical immunology · 1993
• Inactivation of cytochrome P-450 by a troleandomycin metabolite. Protective role of glutathione.The Journal of pharmacology and experimental therapeutics · 1983

via PubMed

Wikidata facts

Subclass of

polyketide

Mass

813.451

Has use

medication

via Wikidata · CC0