NAV

Troleandomycin

Identification

Generic Name
Troleandomycin
DrugBank Accession Number
DB13179
Background

A macrolide antibiotic that is similar to erythromycin.

Type
Small Molecule
Groups
Approved
Structure
Similar Structures
Weight
Average: 813.9684
Monoisotopic: 813.451070479
Chemical Formula
C41H67NO15
Synonyms
  • Oleandocetine
  • Oleandomycin triacetate
  • Oleandomycin triacetyl ester
  • Triacetyloleandomycin
  • Triacetyloleandomycinum
  • Tribiocillina
  • Troleandomicina
  • Troleandomycin
  • Troleandomycine
External IDs
  • NSC-108166
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Pharmacology

Indication

For the treatment of bacterial infection.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Troleandomycin, like other macrolide antibiotics, inhibits bacterial protein synthesis to prevent growth.

Mechanism of action

As a macrolide, troleandomycin binds to the 50S subunit of the bacterial ribosome 2. This binding inhibits translocation of tRNA along the A, P, and E sites of the ribosome. With tRNA unable to move from site to site, amino acids cannot be deposited onto the polypeptide chain leading to failure of protein synthesis. Bacterial cell growth and duplication is inhibited without the ability to generate the necessary proteins.

TargetActionsOrganism
A50S ribosomal protein L32
inhibitor
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
A50S ribosomal protein L4
inhibitor
Escherichia coli (strain K12)
UNuclear receptor subfamily 1 group I member 2
activator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Troleandomycin inhibits clearance of theophylline and can increase the likelyhood of toxicity in patients recieving theophylline therapy 1.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Troleandomycin.
AbametapirThe serum concentration of Troleandomycin can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Troleandomycin.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Troleandomycin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Troleandomycin.
Food Interactions
Not Available

Products

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International/Other Brands
Tao / Triocetin

Categories

ATC Codes
J01FA08 — Troleandomycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Tetracarboxylic acids and derivatives / Macrolides and analogues / O-glycosyl compounds / Oxanes / Monosaccharides / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters / Ketones / Lactones
show 7 more
Substituents
Acetal / Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Aminoglycoside core / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Ether
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
epoxide, macrolide antibiotic, acetate ester, monosaccharide derivative, polyketide, semisynthetic derivative (CHEBI:45735) / Macrolides and lactone polyketides (C12753) / Macrolides and lactone polyketides (LMPK04000042)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
C4DZ64560D
CAS number
2751-09-9
InChI Key
LQCLVBQBTUVCEQ-QTFUVMRISA-N
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
IUPAC Name
(3R,5R,6S,7S,8R,11R,12S,13R,14S,15S)-14-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyloxan-2-yl]oxy}-12-{[(2R,4S,5S,6S)-5-(acetyloxy)-4-methoxy-6-methyloxan-2-yl]oxy}-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadecan-6-yl acetate
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@@]3(CO3)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

References

General References
  1. Weinberger M, Hudgel D, Spector S, Chidsey C: Inhibition of theophylline clearance by troleandomycin. J Allergy Clin Immunol. 1977 Mar;59(3):228-31. [Article]
  2. 5. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 614, 631-632). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
Human Metabolome Database
HMDB0015448
KEGG Drug
D01322
KEGG Compound
C12753
PubChem Compound
202225
PubChem Substance
347829281
ChemSpider
16707
BindingDB
50370258
RxNav
10864
ChEBI
45735
ChEMBL
CHEMBL564085
ZINC
ZINC000169307271
Therapeutic Targets Database
DAP000411
PharmGKB
PA127840611
PDBe Ligand
TAO
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Troleandomycin
MSDS
Download (52.3 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)812.49MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0192 mg/mLALOGPS
logP3.76ALOGPS
logP4.3Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.62Chemaxon
pKa (Strongest Basic)7.87Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area184.19 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity201.15 m3·mol-1Chemaxon
Polarizability86.05 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9048
Blood Brain Barrier-0.945
Caco-2 permeable-0.522
P-glycoprotein substrateSubstrate0.662
P-glycoprotein inhibitor IInhibitor0.9188
P-glycoprotein inhibitor IINon-inhibitor0.631
Renal organic cation transporterNon-inhibitor0.8177
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9075
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9223
Ames testAMES toxic0.5213
CarcinogenicityNon-carcinogens0.8564
BiodegradationNot ready biodegradable0.9949
Rat acute toxicity2.2177 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9881
hERG inhibition (predictor II)Non-inhibitor0.9163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0zfs-7300000900-bff5a68ff1f919f77c4e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ik9-0110000980-12827e61b53c50a1c209
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-2000051930-bd935b9ed7c1cbd66a48
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-114r-0920000410-0efc6458cebdd52b7691
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000010120-ec9453de444009eca657
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0m0b-0920002320-b87008841b3fe1b2b6cf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9310021210-29f003213d75715b1838
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-316.9731097
predicted
DarkChem Lite v0.1.0
[M-H]-275.3278
predicted
DeepCCS 1.0 (2019)
[M+H]+317.2848097
predicted
DarkChem Lite v0.1.0
[M+H]+277.04092
predicted
DeepCCS 1.0 (2019)
[M+Na]+317.4453097
predicted
DarkChem Lite v0.1.0
[M+Na]+283.19778
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Details1. 50S ribosomal protein L32
Kind
Protein
Organism
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of ribosome
Specific Function
Forms a cluster with L17 and L22, and with L22, a pair of "tweezers" that hold together all the domains of the 23S rRNA. Interacts with the antibiotic troleandomycin which blocks the peptide exit t...
Gene Name
rpmF
Uniprot ID
P49228
Uniprot Name
50S ribosomal protein L32
Molecular Weight
6791.905 Da
References
  1. Scharre KA, Eckels DD, Gershwin ME: Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5. [Article]
Details2. 50S ribosomal protein L4
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
One of the primary rRNA binding proteins, this protein initially binds near the 5'-end of the 23S rRNA (PubMed:3298242). It is important during the early stages of 50S assembly (PubMed:3298242). It makes multiple contacts with different domains of the 23S rRNA in the assembled 50S subunit and ribosome (PubMed:7556101, PubMed:6170935).
Specific Function
Bacterial-type rna polymerase transcriptional repressor activity, sequence-specific dna binding
Gene Name
rplD
Uniprot ID
P60723
Uniprot Name
50S ribosomal protein L4
Molecular Weight
22086.36 Da
References
  1. Scharre KA, Eckels DD, Gershwin ME: Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5. [Article]
Details3. Nuclear receptor subfamily 1 group I member 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Kobayashi K, Yamagami S, Higuchi T, Hosokawa M, Chiba K: Key structural features of ligands for activation of human pregnane X receptor. Drug Metab Dispos. 2004 Apr;32(4):468-72. [Article]

Enzymes

Details1. Cytochrome P450 3A43
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
References
  1. Ledirac N, de Sousa G, Fontaine F, Agouridas C, Gugenheim J, Lorenzon G, Rahmani R: Effects of macrolide antibiotics on CYP3A expression in human and rat hepatocytes: interspecies differences in response to troleandomycin. Drug Metab Dispos. 2000 Dec;28(12):1391-3. [Article]
Details2. Cytochrome P450 2C8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
In vitro study demonstrates a reversible inhibition of recombinant CYP2C8 with an IC50 of 953.0 µM.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
Details3. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Drug Interactions & Labeling - FDA [Link]
Details4. Cytochrome P450 3A7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions & Labeling - FDA [Link]
Details5. Cytochrome P450 3A5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Klees TM, Sheffels P, Dale O, Kharasch ED: Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11. Epub 2004 Nov 22. [Article]
  2. Drug Interactions & Labeling - FDA [Link]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
  2. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [Article]
  3. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [Article]

Drug created at July 06, 2007 19:54 / Updated at February 21, 2021 18:54