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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363853 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6972981 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | TAO Approved UseUnknown Launch Date-1.8921599E10 |
Doses
Dose | Population | Adverse 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 Sources: Page: p.327Anicteric cholestasis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 4.0 |
yes [IC50 0.28 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15557344/ Page: 4.0 |
yes [IC50 0.62 uM] | |||
yes [IC50 517.6 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11716514/ Page: 4.0 |
yes [IC50 68.3 uM] | |||
yes [IC50 953 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/mtm/troleandomycin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8948090
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
Edited
Sat Jun 26 08:45:19 UTC 2021
by
admin
on
Sat Jun 26 08:45:19 UTC 2021
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Record UNII |
C4DZ64560D
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J01FA08
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WHO-VATC |
QJ01FA08
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NCI_THESAURUS |
C261
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FDA ORPHAN DRUG |
39089
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C4DZ64560D
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10864
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SUB11333MIG
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220-392-9
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2751-09-9
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M11219
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805
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C66643
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2769
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TROLEANDOMYCIN
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DB01361
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CHEMBL564085
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