Tildipirosin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Tildipirosin
Accession Number
DB11470
Type
Small Molecule
Groups
Vet approved
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
S795AT66JB
CAS number
Not Available
Weight
Average: 734.032
Monoisotopic: 733.524116258
Chemical Formula
C41H71N3O8
InChI Key
HNDXPZPJZGTJLJ-UEJFNEDBSA-N
InChI
InChI=1S/C41H71N3O8/c1-8-35-32(26-44-20-13-10-14-21-44)23-27(2)15-16-33(45)28(3)24-31(17-22-43-18-11-9-12-19-43)40(29(4)34(46)25-36(47)51-35)52-41-39(49)37(42(6)7)38(48)30(5)50-41/h15-16,23,28-32,34-35,37-41,46,48-49H,8-14,17-22,24-26H2,1-7H3/b16-15+,27-23+/t28-,29+,30-,31+,32-,34-,35-,37+,38-,39-,40-,41+/m1/s1
IUPAC Name
(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-{[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-16-ethyl-4-hydroxy-5,9,13-trimethyl-7-[2-(piperidin-1-yl)ethyl]-15-[(piperidin-1-yl)methyl]-1-oxacyclohexadeca-11,13-diene-2,10-dione
SMILES
[H]\C1=C([H])/C(=O)[C@]([H])(C)C[C@]([H])(CCN2CCCCC2)[C@]([H])(O[C@]2([H])O[C@]([H])(C)[C@@]([H])(O)[C@]([H])(N(C)C)[C@@]2([H])O)[C@@]([H])(C)[C@]([H])(O)CC(=O)O[C@]([H])(CC)[C@@]([H])(CN2CCCCC2)C([H])=C1C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Tildipirosin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Tildipirosin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Tildipirosin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Tildipirosin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Tildipirosin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Tildipirosin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Tildipirosin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Tildipirosin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Tildipirosin.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Tildipirosin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Menge M, Rose M, Bohland C, Zschiesche E, Kilp S, Metz W, Allan M, Ropke R, Nurnberger M: Pharmacokinetics of tildipirosin in bovine plasma, lung tissue, and bronchial fluid (from live, nonanesthetized cattle). J Vet Pharmacol Ther. 2012 Dec;35(6):550-9. doi: 10.1111/j.1365-2885.2011.01349.x. Epub 2011 Dec 21. [PubMed:22188102]
  2. Andersen NM, Poehlsgaard J, Warrass R, Douthwaite S: Inhibition of protein synthesis on the ribosome by tildipirosin compared with other veterinary macrolides. Antimicrob Agents Chemother. 2012 Nov;56(11):6033-6. doi: 10.1128/AAC.01250-12. Epub 2012 Aug 27. [PubMed:22926570]
  3. Poehlsgaard J, Andersen NM, Warrass R, Douthwaite S: Visualizing the 16-membered ring macrolides tildipirosin and tilmicosin bound to their ribosomal site. ACS Chem Biol. 2012 Aug 17;7(8):1351-5. doi: 10.1021/cb300105p. Epub 2012 May 14. [PubMed:22563863]
  4. Michael GB, Eidam C, Kadlec K, Meyer K, Sweeney MT, Murray RW, Watts JL, Schwarz S: Increased MICs of gamithromycin and tildipirosin in the presence of the genes erm(42) and msr(E)-mph(E) for bovine Pasteurella multocida and Mannheimia haemolytica. J Antimicrob Chemother. 2012 Jun;67(6):1555-7. doi: 10.1093/jac/dks076. Epub 2012 Mar 7. [PubMed:22398653]
  5. Rose M, Menge M, Bohland C, Zschiesche E, Wilhelm C, Kilp S, Metz W, Allan M, Ropke R, Nurnberger M: Pharmacokinetics of tildipirosin in porcine plasma, lung tissue, and bronchial fluid and effects of test conditions on in vitro activity against reference strains and field isolates of Actinobacillus pleuropneumoniae. J Vet Pharmacol Ther. 2013 Apr;36(2):140-53. doi: 10.1111/j.1365-2885.2012.01397.x. Epub 2012 Apr 15. [PubMed:22500881]
  6. Gautier-Bouchardon AV, Ferre S, Le Grand D, Paoli A, Gay E, Poumarat F: Overall decrease in the susceptibility of Mycoplasma bovis to antimicrobials over the past 30 years in France. PLoS One. 2014 Feb 4;9(2):e87672. doi: 10.1371/journal.pone.0087672. eCollection 2014. [PubMed:24503775]
  7. Rose M, Pridmore A, Shaw A, Wilhelm C, Menge M, Kilp S, Ropke R, Nurnberger M: A microbiological assay to estimate the antimicrobial activity of parenteral tildipirosin against foodborne pathogens and commensals in the colon of beef cattle and pigs. J Vet Pharmacol Ther. 2016 Jun;39(3):277-86. doi: 10.1111/jvp.12277. Epub 2015 Nov 5. [PubMed:26538405]
  8. Dieste-Perez L, Fraile L, de Miguel MJ, Barberan M, Blasco JM, Munoz PM: Studies on a suitable antibiotic therapy for treating swine brucellosis. J Vet Pharmacol Ther. 2015 Aug;38(4):357-64. doi: 10.1111/jvp.12189. Epub 2014 Nov 21. [PubMed:25413993]
  9. Dickson LC: Performance characterization of a quantitative liquid chromatography-tandem mass spectrometric method for 12 macrolide and lincosamide antibiotics in salmon, shrimp and tilapia. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Sep 15;967:203-10. doi: 10.1016/j.jchromb.2014.07.031. Epub 2014 Jul 27. [PubMed:25125397]
  10. Emmerich IU: [New drugs for horses and production animals in 2011]. Tierarztl Prax Ausg G Grosstiere Nutztiere. 2012 Oct 17;40(5):301-8. [PubMed:23076759]
External Links
ChemSpider
30790722
ChEMBL
CHEMBL3039509

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0548 mg/mLALOGPS
logP3.75ALOGPS
logP4.46ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.68ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area132.24 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity206.76 m3·mol-1ChemAxon
Polarizability84.85 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Macrolides and analogues / Hexoses / O-glycosyl compounds / Piperidines / Oxanes / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters / Cyclic ketones / Trialkylamines
show 10 more
Substituents
Aminoglycoside core / Macrolide / Hexose monosaccharide / O-glycosyl compound / Glycosyl compound / Monosaccharide / Oxane / Piperidine / Tertiary aliphatic amine / Tertiary amine
show 23 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
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. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. [PubMed:11020135]

Drug created on February 25, 2016 12:01 / Updated on June 04, 2019 07:22