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

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H67NO15
Molecular Weight 813.9684
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROLEANDOMYCIN

SMILES

CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3OC(C)=O)N(C)C)[C@@H](C)C[C@@]4(CO4)C(=O)[C@H](C)[C@@H](OC(C)=O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1OC(C)=O

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 813.9684
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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
Primary
TAO
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
Cytochrome P4502B6 and 2C9 do not metabolize midazolam: kinetic analysis and inhibition study with monoclonal antibodies.
2001 Apr
Halothane-dependent lipid peroxidation in human liver microsomes is catalyzed by cytochrome P4502A6 (CYP2A6).
2001 Aug
Stereoselective metabolism of cisapride and enantiomer-enantiomer interaction in human cytochrome P450 enzymes: major role of CYP3A.
2001 Aug
Identification of cytochrome P-450 isoforms responsible for cis-tramadol metabolism in human liver microsomes.
2001 Aug
A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans.
2001 Dec
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
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
2002 Dec
O-Dealkylation of fluoxetine in relation to CYP2C19 gene dose and involvement of CYP3A4 in human liver microsomes.
2002 Jan
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.
2002 Jul
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.
2002 Jun 1
The gastroprokinetic and antiemetic drug metoclopramide is a substrate and inhibitor of cytochrome P450 2D6.
2002 Mar
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
Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine.
2003 Dec 3
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.
2003 Jan 1
In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4, and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation.
2003 Jun
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
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

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:46:15 UTC 2019
Edited
by admin
on Mon Oct 21 19:46:15 UTC 2019
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 Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
WHO-VATC QJ01FA08
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
NCI_THESAURUS C261
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
FDA ORPHAN DRUG 39089
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
Code System Code Type Description
RXCUI
10864
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY RxNorm
EVMPD
SUB11333MIG
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
ECHA (EC/EINECS)
220-392-9
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
CAS
2751-09-9
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
MERCK INDEX
M11219
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY Merck Index
INN
805
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
NCI_THESAURUS
C66643
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
MESH
D014217
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
WIKIPEDIA
TROLEANDOMYCIN
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
PUBCHEM
202225
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
EPA CompTox
2751-09-9
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
DRUG BANK
DB01361
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
ChEMBL
CHEMBL564085
Created by admin on Mon Oct 21 19:46:15 UTC 2019 , Edited by admin on Mon Oct 21 19:46:15 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
Related Record Type Details
ACTIVE MOIETY