U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H67NO15
Molecular Weight 813.97
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROLEANDOMYCIN

SMILES

C[C@@]1([H])C[C@@]2(CO2)C(=O)[C@]([H])(C)[C@]([H])([C@@]([H])(C)[C@@]([H])(C)OC(=O)[C@]([H])(C)[C@]([H])([C@]([H])(C)[C@@]1([H])O[C@@]3([H])[C@@]([H])([C@]([H])(C[C@@]([H])(C)O3)N(C)C)OC(=O)C)O[C@@]4([H])C[C@@]([H])([C@]([H])([C@]([H])(C)O4)OC(=O)C)OC)OC(=O)C

InChI

InChIKey=LQCLVBQBTUVCEQ-QTFUVMRISA-N
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

HIDE SMILES / InChI

Molecular Formula C41H67NO15
Molecular Weight 813.97
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Troleandomycin (also known Triacetyl-oleandomycin and having brand name Tao) is a macrolide antibiotic which used to for the treat of infections of the upper and lower respiratory tract: such as tonsillitis, bronchitis, sinusitis, and pneumonia. However, the brand name Tao was discontinued. Troleandomycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the "P" or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the "A" or acceptor site to the "P" or donor site is prevented, and subsequent protein synthesis is inhibited.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TAO

Launch Date

-18921600000
Doses

Doses

DosePopulationAdverse events​
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: F
Sources:
Disc. AE: Hepatitis, Anicteric cholestasis...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Anicteric cholestasis
Sources:
AEs

AEs

AESignificanceDosePopulation
Anicteric cholestasis Disc. AE
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: F
Sources:
Hepatitis Disc. AE
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Pharmacokinetic aspects of treating infections in the intensive care unit: focus on drug interactions.
2001
Clinically significant drug interactions with agents specific for migraine attacks.
2001
Coupling of a supercritical fluid chromatography system to a hybrid (Q-TOF 2) mass spectrometer: on-line accurate mass measurements.
2001
Cytochrome P4502B6 and 2C9 do not metabolize midazolam: kinetic analysis and inhibition study with monoclonal antibodies.
2001 Apr
Role of cytochrome P450 in estradiol metabolism in vitro.
2001 Feb
Troglitazone quinone formation catalyzed by human and rat CYP3A: an atypical CYP oxidation reaction.
2001 Jul 15
Indirect cytotoxicity of flucloxacillin toward human biliary epithelium via metabolite formation in hepatocytes.
2001 Jun
Comparative analysis of in vitro and in vivo pharmacokinetic parameters related to individual variability of GTS-21 in canine.
2002
Identification of a novel route of extraction of sirolimus in human small intestine: roles of metabolism and secretion.
2002 Apr
CYP3A4 active site volume modification by mutagenesis of leucine 211.
2002 Apr
Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals.
2002 Dec
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
2002 Dec
Effects of olopatadine, a new antiallergic agent, on human liver microsomal cytochrome P450 activities.
2002 Dec
Enzyme kinetics for the formation of 3-hydroxyquinine and three new metabolites of quinine in vitro; 3-hydroxylation by CYP3A4 is indeed the major metabolic pathway.
2002 Dec
Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: differential metabolism by CYP3A4 and CYP3A5.
2002 Dec
Effect of caffeine on acetaminophen hepatotoxicity in cultured hepatocytes treated with ethanol and isopentanol.
2002 Dec 1
Involvement of cytochrome P450 in the metabolism of rebamipide by the human liver.
2002 Jul
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.
2002 Jul
Metabolism of a novel phosphodiesterase-IV inhibitor (V11294) by human hepatic cytochrome P450 forms.
2002 Jun
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.
2002 Jun 1
Human cytochrome P450s involved in the metabolism of 9-cis- and 13-cis-retinoic acids.
2002 Mar 1
Cytochrome P450 3A4 and P-glycoprotein mediate the interaction between an oral erythromycin breath test and rifampin.
2002 Nov
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
2002 Oct
Alternate treatments in asthma.
2003 Apr
Simultaneous assessment of drug interactions with low- and high-extraction opioids: application to parecoxib effects on the pharmacokinetics and pharmacodynamics of fentanyl and alfentanil.
2003 Apr
Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine.
2003 Dec 3
Inhibitory effect of troleandomycin on the metabolism of omeprazole is CYP2C19 genotype-dependent.
2003 Feb
TNF-alpha -induced endothelial cell adhesion molecule expression is cytochrome P-450 monooxygenase dependent.
2003 Feb
Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine.
2003 Jan
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.
2003 Jan 1
Identification of novel enzyme-prodrug combinations for use in cytochrome P450-based gene therapy for cancer.
2003 Jan 1
Atorvastatin reduces the ability of clopidogrel to inhibit platelet aggregation: a new drug-drug interaction.
2003 Jan 7
The human hepatic metabolism of simvastatin hydroxy acid is mediated primarily by CYP3A, and not CYP2D6.
2003 Jul
Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein.
2003 Jul
Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir.
2003 Mar
Structural insight into the role of the ribosomal tunnel in cellular regulation.
2003 May
Disposition of tacrolimus in isolated perfused rat liver: influence of troleandomycin, cyclosporine, and gg918.
2003 Nov
Evaluation of hepatotoxic potential of drugs by inhibition of bile-acid transport in cultured primary human hepatocytes and intact rats.
2003 Nov
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003 Nov 17
An evaluation of a low-density DNA microarray using cytochrome P450 inducers.
2003 Sep
Demethylation of radiolabelled dextromethorphan in rat microsomes and intact hepatocytes.
2003 Sep
Key structural features of ligands for activation of human pregnane X receptor.
2004 Apr
CYP3A4 is a human microsomal vitamin D 25-hydroxylase.
2004 Apr
Utility of microtiter plate assays for human cytochrome P450 inhibition studies in drug discovery: application of simple method for detecting quasi-irreversible and irreversible inhibitors.
2004 Feb
Large interindividual variability in the in vitro formation of tamoxifen metabolites related to the development of genotoxicity.
2004 Jan
Sulfoxidation of cysteine and mercapturic acid conjugates of the sevoflurane degradation product fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether (compound A).
2004 Mar
Intravenous and oral alfentanil as in vivo probes for hepatic and first-pass cytochrome P450 3A activity: noninvasive assessment by use of pupillary miosis.
2004 Nov
Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadone.
2004 Sep
CYP3A4 is a vitamin D-24- and 25-hydroxylase: analysis of structure function by site-directed mutagenesis.
2005 Feb
Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes.
2005 Mar
Patents

Sample Use Guides

Usual Adult Dose for Pneumonia: 250 to 500 mg orally 4 times a day.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:45:19 UTC 2021
Edited
by admin
on Sat Jun 26 08:45:19 UTC 2021
Record UNII
C4DZ64560D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROLEANDOMYCIN
INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
OLEANDOMYCIN (AS TROLEANDOMYCIN)
VANDF  
Common Name English
OLEANDOMYCIN (AS TROLEANDOMYCIN) [VANDF]
Common Name English
NSC-108166
Code English
OLEANDOMYCIN TRIACETATE ESTER
Common Name English
TROLEANDOMYCIN [USP]
Common Name English
TROLEANDOMYCIN [MI]
Common Name English
TROLEANDOMYCIN [WHO-DD]
Common Name English
TRIACETYLOLEANDOMYCIN [JAN]
Common Name English
TROLEANDOMYCIN [ORANGE BOOK]
Common Name English
TROLEANDOMYCIN [MART.]
Common Name English
TROLEANDOMYCIN [VANDF]
Common Name English
TRIACETYLOLEANDOMYCIN
JAN  
Common Name English
TROLEANDOMYCIN [INN]
Common Name English
TROLEANDOMYCIN [USAN]
Common Name English
Classification Tree Code System Code
WHO-ATC J01FA08
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
WHO-VATC QJ01FA08
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
NCI_THESAURUS C261
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
FDA ORPHAN DRUG 39089
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
Code System Code Type Description
FDA UNII
C4DZ64560D
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
RXCUI
10864
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY RxNorm
EVMPD
SUB11333MIG
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
220-392-9
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
CAS
2751-09-9
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
MERCK INDEX
M11219
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY Merck Index
INN
805
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
NCI_THESAURUS
C66643
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
MESH
D014217
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
DRUG CENTRAL
2769
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
WIKIPEDIA
TROLEANDOMYCIN
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
PUBCHEM
202225
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
EPA CompTox
2751-09-9
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
DRUG BANK
DB01361
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL564085
Created by admin on Sat Jun 26 08:45:19 UTC 2021 , Edited by admin on Sat Jun 26 08:45:19 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
Related Record Type Details
ACTIVE MOIETY