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]
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Therapeutic Class

Antibiotics

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[3]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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]
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⏷ 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]