Tiamulin

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

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Tiamulin
Accession Number
DB11468
Type
Small Molecule
Groups
Vet approved
Description

Tiamulin is a pleuromutilin antibiotic drug that is used in veterinary medicine particularly for pigs and poultry.

Structure
Thumb
Synonyms
  • Tiamulin
  • Tiamulina
  • Tiamuline
  • Tiamulinum
External IDs
SQ 14055
Product Ingredients
IngredientUNIICASInChI Key
Tiamulin hydrogen fumarateION1Q02ZCX55297-96-6YXQXDXAHCSEVSD-GCYNEOGWSA-N
Categories
UNII
E38WZ4U54R
CAS number
55297-95-5
Weight
Average: 493.742
Monoisotopic: 493.322579687
Chemical Formula
C28H47NO4S
InChI Key
UURAUHCOJAIIRQ-QGLSALSOSA-N
InChI
InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1
IUPAC Name
(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate
SMILES
[H][C@@]12C(=O)CC[C@]11CC[C@@]([H])(C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]1C)OC(=O)CSCCN(CC)CC

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
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
(R)-warfarinThe risk or severity of bleeding can be increased when Tiamulin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Tiamulin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Tiamulin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Tiamulin is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Tiamulin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Tiamulin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Tiamulin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Tiamulin.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Tiamulin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Tiamulin.
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.

    Learn more
  • Evidence Level
    Evidence Level

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

    Learn more
  • Action
    Action

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

    Learn more
Food Interactions
Not Available

References

General References
  1. Bouwkamp FT: [Tiamulin: a dangerous drug?]. Tijdschr Diergeneeskd. 1987 Nov 15;112(22):1295-6. [PubMed:3686511]
  2. Miller DJ: Monensin-tiamulin interaction. Vet Rec. 1981 Apr 4;108(14):317-8. [PubMed:7233787]
  3. Miller DJ, O'Connor JJ, Roberts NL: Tiamulin/salinomycin interactions in pigs. Vet Rec. 1986 Jan 18;118(3):73-5. [PubMed:3952946]
  4. Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 6;163(23):698; author reply 698. [PubMed:19060324]
  5. Pott JM, Shov B: Monensin--tiamulin interactions in pigs. Vet Rec. 1981 Dec 12;109(24):545. [PubMed:7340095]
  6. Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 20-27;163(25):760. [PubMed:19103625]
  7. Ziv G, Levisohn SL, Bar-Moshe B, Bor A, Soback S: Clinical pharmacology of tiamulin in ruminants. J Vet Pharmacol Ther. 1983 Mar;6(1):23-32. [PubMed:6854730]
  8. Wanner M: [Tiamulin and salinomycin intolerance in swine]. Schweiz Arch Tierheilkd. 1984 Oct;126(10):521-6. [PubMed:6505670]
  9. Horrox NE: Monensin-tiamulin interaction risk to poultry. Vet Rec. 1980 Mar 22;106(12):278. [PubMed:7376381]
  10. Rubin JE, Ball KR, Chirino-Trejo M: Decreased susceptibility of MRSA ST398 to tiamulin. Vet Microbiol. 2011 Aug 5;151(3-4):422-3. doi: 10.1016/j.vetmic.2011.03.030. Epub 2011 Apr 1. [PubMed:21511410]
  11. Szucs G, Tamasi V, Laczay P, Monostory K: Biochemical background of toxic interaction between tiamulin and monensin. Chem Biol Interact. 2004 Mar 15;147(2):151-61. [PubMed:15013817]
  12. Pringle M, Landen A, Franklin A: Tiamulin resistance in porcine Brachyspira pilosicoli isolates. Res Vet Sci. 2006 Feb;80(1):1-4. Epub 2005 Apr 2. [PubMed:16253666]
  13. De Baere S, Devreese M, Maes A, De Backer P, Croubels S: Quantification of 8-alpha-hydroxy-mutilin as marker residue for tiamulin in rabbit tissues by high-performance liquid chromatography-mass spectrometry. Anal Bioanal Chem. 2015 Jun;407(15):4437-45. doi: 10.1007/s00216-014-8437-9. Epub 2015 Jan 16. [PubMed:25592328]
  14. Ross RF, Cox DF: Evaluation of tiamulin for treatment of mycoplasmal pneumonia in swine. J Am Vet Med Assoc. 1988 Aug 15;193(4):441-6. [PubMed:3170319]
External Links
KEGG Drug
D06127
KEGG Compound
C12065
ChemSpider
571196
ChEBI
44137
ChEMBL
CHEMBL1234521
HET
MUL
Wikipedia
Tiamulin
PDB Entries
1xbp / 3g4s

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 Solubility0.000524 mg/mLALOGPS
logP4.47ALOGPS
logP4.5ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.43ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.74 m3·mol-1ChemAxon
Polarizability57.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-1910000000-dcba10789dcdb073f414
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900300000-69e826135bba34d65b0f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-330cc01e25deade8bdcb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0910000000-7a7403b84fe0b950a42e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-0900000000-680b97999b88640ad153
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0000900000-93e5960b0d906f842e50

Taxonomy

Description
This compound belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Diterpenoids
Direct Parent
Pleuromutilin and derivatives
Alternative Parents
Trialkylamines / Secondary alcohols / Ketones / Carboxylic acid esters / Amino acids and derivatives / Sulfenyl compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Pleuromutilin / Amino acid or derivatives / Carboxylic acid ester / Ketone / Secondary alcohol / Tertiary amine / Tertiary aliphatic amine / Dialkylthioether / Sulfenyl compound / Monocarboxylic acid or derivatives
show 14 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cyclic ketone, tertiary amino compound, carboxylic ester, secondary alcohol, organic sulfide, semisynthetic derivative, carbotricyclic compound, tetracyclic diterpenoid (CHEBI:44137)

Drug created on February 25, 2016 12:00 / Updated on September 02, 2019 21:52