Details of the Drug

General Information of Drug (ID: DMUZNIG)

Drug Name
Troleandomycin
Synonyms
Aovine; Cyclamycin; Evramicina; Matromicina; Oleandocetin; Oleandocetine; TAO; Treolmicina; Triacetyloleandomycin; Triacetyloleandomycinum; Tribiocillina; Triocetin; Triolan; Troleandomicina; Troleandomycine; Troleandomycinum; Viamicina; Wytrion; Matromycin T; Oleandomycin triacetate; Oleandomycin triacetyl ester; Triacetyl ester of oleandomycin; WY 651; Tao (TN); Tao (VAN); Tekmisin (TN); Treis-Micina; Triacetyloleandomycin (JAN); Triocetin (TN); Troleandomicina [INN-Spanish]; Troleandomycin (TAO); Troleandomycin [USAN:INN]; Troleandomycine [INN-French]; Troleandomycinum [INN-Latin]; Oleandomycin, triacetate (ester); T.A.O; Troleandomycin (USP/INN); T.A.O.
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01FA08: Troleandomycin
J01FA: Macrolides
J01F: MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 814
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 16
Chemical Identifiers
Formula
C41H67NO15
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
Canonical 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
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
InChIKey
LQCLVBQBTUVCEQ-QTFUVMRISA-N
Cross-matching ID
PubChem CID
202225
ChEBI ID
CHEBI:45735
CAS Number
2751-09-9
UNII
C4DZ64560D
DrugBank ID
DB13179
TTD ID
D06IGU
VARIDT ID
DR00543
INTEDE ID
DR1652

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA) TTUWYEA NOUNIPROTAC Binder [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Troleandomycin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Troleandomycin and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [6]
Ivosidenib DM8S6T7 Major Decreased metabolism of Troleandomycin caused by Ivosidenib mediated inhibition of CYP450 enzyme. Acute myeloid leukaemia [2A60] [7]
Oliceridine DM6MDCF Major Decreased metabolism of Troleandomycin caused by Oliceridine mediated inhibition of CYP450 enzyme. Acute pain [MG31] [8]
Ripretinib DM958QB Major Decreased metabolism of Troleandomycin caused by Ripretinib mediated inhibition of CYP450 enzyme. Gastrointestinal stromal tumour [2B5B] [6]
Avapritinib DMK2GZX Major Decreased metabolism of Troleandomycin caused by Avapritinib mediated inhibition of CYP450 enzyme. Gastrointestinal stromal tumour [2B5B] [9]
Pemigatinib DM819JF Major Decreased metabolism of Troleandomycin caused by Pemigatinib mediated inhibition of CYP450 enzyme. Liver cancer [2C12] [10]
Pralsetinib DMWU0I2 Major Decreased metabolism of Troleandomycin caused by Pralsetinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Selpercatinib DMZR15V Major Decreased metabolism of Troleandomycin caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [12]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Troleandomycin and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [13]
Ubrogepant DM749I3 Major Decreased metabolism of Troleandomycin caused by Ubrogepant mediated inhibition of CYP450 enzyme. Migraine [8A80] [14]
Upadacitinib DM32B5U Major Decreased metabolism of Troleandomycin caused by Upadacitinib mediated inhibition of CYP450 enzyme. Rheumatoid arthritis [FA20] [15]
Voxelotor DMCS6M5 Major Decreased metabolism of Troleandomycin caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [16]
Larotrectinib DM26CQR Major Decreased metabolism of Troleandomycin caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [6]
Fluticasone DMGCSVF Major Decreased metabolism of Troleandomycin caused by Fluticasone mediated inhibition of CYP450 enzyme. Vasomotor/allergic rhinitis [CA08] [17]
⏷ Show the Full List of 14 DDI Information of This Drug

References

1 Drug Information of Dihydrotachysterol from nextbio research in illumina. 2015.
2 Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5.
3 Effects of roxithromycin, erythromycin and troleandomycin on their N-demethylation by rat and human cytochrome P450 enzymes. Xenobiotica. 1996 Nov;26(11):1143-53.
4 A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97.
5 Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11.
6 Cerner Multum, Inc. "Australian Product Information.".
7 Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA.
8 Gunston GD, Mehta U "Potentially serious drug interactions with grapefruit juice." S Afr Med J 90 (2000): 41. [PMID: 10721388]
9 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
10 Product Information. Pemazyre (pemigatinib). Incyte Corporation, Wilmington, DE.
11 Product Information. Gavreto (pralsetinib). Blueprint Medicines Corporation, Cambridge, MA.
12 Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
13 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
14 Product Information. Ubrelvy (ubrogepant). Allergan Inc, Irvine, CA.
15 Product Information. Rinvoq (upadacitinib). AbbVie US LLC, North Chicago, IL.
16 Bailey DG, Arnold JMO, Spence JD "Grapefruit juice and drugs - how significant is the interaction." Clin Pharmacokinet 26 (1994): 91-8. [PMID: 8162660]
17 Arrington-Sanders R, Hutton N, Siberry GK "Ritonavir-fluticasone interaction causing Cushing syndrome in HIV-infected children and adolescents." Pediatr Infect Dis J 25 (2006): 1044-1048. [PMID: 17072128]