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

Identification

Generic Name
Tiamulin
DrugBank Accession Number
DB11468
Background

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

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 493.742
Monoisotopic: 493.322579687
Chemical Formula
C28H47NO4S
Synonyms
  • Tiamulin
  • Tiamulina
  • Tiamuline
  • Tiamulinum
External IDs
  • SQ 14055

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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
AcenocoumarolThe risk or severity of bleeding can be increased when Tiamulin is combined with Acenocoumarol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tiamulin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Bupivacaine.
ButacaineThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Butacaine.
ButambenThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Butamben.
CapsaicinThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Capsaicin.
ChloroprocaineThe risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Chloroprocaine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tiamulin hydrogen fumarateION1Q02ZCX55297-96-6YXQXDXAHCSEVSD-GCYNEOGWSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic homopolycyclic compound / Amine / Amino acid or derivatives / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkylthioether / Hydrocarbon derivative / Ketone
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)
Affected organisms
Not Available

Chemical Identifiers

UNII
E38WZ4U54R
CAS number
55297-95-5
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

References

General References
  1. Bouwkamp FT: [Tiamulin: a dangerous drug?]. Tijdschr Diergeneeskd. 1987 Nov 15;112(22):1295-6. [Article]
  2. Miller DJ: Monensin-tiamulin interaction. Vet Rec. 1981 Apr 4;108(14):317-8. [Article]
  3. Miller DJ, O'Connor JJ, Roberts NL: Tiamulin/salinomycin interactions in pigs. Vet Rec. 1986 Jan 18;118(3):73-5. [Article]
  4. Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 6;163(23):698; author reply 698. [Article]
  5. Pott JM, Shov B: Monensin--tiamulin interactions in pigs. Vet Rec. 1981 Dec 12;109(24):545. [Article]
  6. Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 20-27;163(25):760. [Article]
  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. [Article]
  8. Wanner M: [Tiamulin and salinomycin intolerance in swine]. Schweiz Arch Tierheilkd. 1984 Oct;126(10):521-6. [Article]
  9. Horrox NE: Monensin-tiamulin interaction risk to poultry. Vet Rec. 1980 Mar 22;106(12):278. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D06127
KEGG Compound
C12065
ChemSpider
571196
RxNav
1546410
ChEBI
44137
ChEMBL
CHEMBL1234521
ZINC
ZINC000004217557
PDBe Ligand
MUL
Wikipedia
Tiamulin
PDB Entries
1xbp / 3g4s

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection
SolutionOral
Injection, solution
Granule, for solution
GranuleOral200 g/kg
GranuleOral100 g/kg
GranuleOral
Powder, for solution
Powder
GranuleOral800 mg/g
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

Drug created at February 25, 2016 19:00 / Updated at February 21, 2021 18:53