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

Approved Use

Unknown

Launch Date

-1.8921599E10
Doses

Doses

DosePopulationAdverse events​
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources: Page: p.327
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: bronchitis
Age Group: 62
Sex: F
Population Size: 1
Sources: Page: p.327
Disc. AE: Hepatitis, Anicteric cholestasis...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Anicteric cholestasis
Sources: Page: p.327
AEs

AEs

AESignificanceDosePopulation
Anicteric cholestasis Disc. AE
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources: Page: p.327
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: bronchitis
Age Group: 62
Sex: F
Population Size: 1
Sources: Page: p.327
Hepatitis Disc. AE
2 g multiple, oral
Recommended
Dose: 2 g
Route: oral
Route: multiple
Dose: 2 g
Sources: Page: p.327
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: bronchitis
Age Group: 62
Sex: F
Population Size: 1
Sources: Page: p.327
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
negligible [IC50 >1000 uM]
yes [IC50 0.28 uM]
yes [IC50 0.62 uM]
yes [IC50 517.6 uM]
yes [IC50 68.3 uM]
yes [IC50 953 uM]
PubMed

PubMed

TitleDatePubMed
Comparative analysis of in vitro and in vivo pharmacokinetic parameters related to individual variability of GTS-21 in canine.
2002
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
Effect of caffeine on acetaminophen hepatotoxicity in cultured hepatocytes treated with ethanol and isopentanol.
2002 Dec 1
Differential metabolism of midazolam in mouse liver and intestine microsomes: a comparison of cytochrome P450 activity and expression.
2003 Apr
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
Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes.
2003 Aug
Evidence for the involvement of human liver microsomes CYP1A2 in the mono-hydroxylation of daidzein.
2003 Aug
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
Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine.
2003 Jan
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
Upregulation of cytochromes P450 2B in rat liver by orphenadrine.
2003 Jun
In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation.
2003 Jun
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
Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone.
2004 Apr
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
Immunomodulatory activity and effectiveness of macrolides in chronic airway disease.
2004 Feb
High-throughput screening for the assessment of time-dependent inhibitions of new drug candidates on recombinant CYP2D6 and CYP3A4 using a single concentration method.
2004 Jan
Studies on the metabolism of the novel, selective cyclooxygenase-2 inhibitor indomethacin phenethylamide in rat, mouse, and human liver microsomes: identification of active metabolites.
2004 Jan
Large interindividual variability in the in vitro formation of tamoxifen metabolites related to the development of genotoxicity.
2004 Jan
Relationship between content and activity of cytochrome P450 and induction of heterocyclic amine DNA adducts in human liver samples in vivo and in vitro.
2004 Jun
Different in vitro metabolism of paclitaxel and docetaxel in humans, rats, pigs, and minipigs.
2004 Jun
Sulfoxidation of cysteine and mercapturic acid conjugates of the sevoflurane degradation product fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether (compound A).
2004 Mar
CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes.
2004 Mar
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers.
2004 Mar
Biochemical background of toxic interaction between tiamulin and monensin.
2004 Mar 15
Identification of cytochromes P450 2C9 and 3A4 as the major catalysts of phenprocoumon hydroxylation in vitro.
2004 May
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
Cytochrome P450 3A4 is the major enzyme involved in the metabolism of the substance P receptor antagonist aprepitant.
2004 Nov
Role of cytochrome P4503A in cysteine S-conjugates sulfoxidation and the nephrotoxicity of the sevoflurane degradation product fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether (compound A) in rats.
2004 Sep
Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadone.
2004 Sep
Pharmacokinetics of clarithromycin in rats with acute renal failure induced by uranyl nitrate.
2004 Sep
Influence of hepatic and intestinal cytochrome P4503A activity on the acute disposition and effects of oral transmucosal fentanyl citrate.
2004 Sep
Characterization of human cytochrome P450 enzymes catalyzing domperidone N-dealkylation and hydroxylation in vitro.
2004 Sep
CYP3A induction aggravates endotoxemic liver injury via reactive oxygen species in male rats.
2004 Sep 1
Oral erythromycin and the risk of sudden death from cardiac causes.
2004 Sep 9
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. Usual Adult Dose for Streptococcal Infection: 250 to 500 mg orally 4 times a day. Usual Pediatric Dose for Pneumonia: The safety and efficacy of troleandomycin in children < 1 year have not been established. >= 1 year: 125 to 250 mg every 6 hours. When used in streptococcal infections, therapy should be continued for 10 days. Usual Pediatric Dose for Streptococcal Infection: The safety and efficacy of troleandomycin in children < 1 year have not been established. >= 1 year: 125 to 250 mg every 6 hours. When used in streptococcal infections, therapy should be continued for 10 days.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Recombinant 3A4 catalysed very efficiently the N-demethylation of roxithromycin, erythromycin and troleandomycin in reconstituted monooxygenase systems, troleandomycin was able to induce CYP3A1 in rat liver microsomes, and N-demethylation of troleandomycin was catalysed mainly by 3A1 (and partly by 2B1) in rat and by 3A4 in man.
Unknown
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
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ACTIVE MOIETY