Tiamulin
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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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- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Tiamulin is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tiamulin. Benzocaine The risk or severity of methemoglobinemia can be increased when Tiamulin is combined with Benzocaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Tiamulin hydrogen fumarate ION1Q02ZCX 55297-96-6 YXQXDXAHCSEVSD-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
- Bouwkamp FT: [Tiamulin: a dangerous drug?]. Tijdschr Diergeneeskd. 1987 Nov 15;112(22):1295-6. [Article]
- Miller DJ: Monensin-tiamulin interaction. Vet Rec. 1981 Apr 4;108(14):317-8. [Article]
- Miller DJ, O'Connor JJ, Roberts NL: Tiamulin/salinomycin interactions in pigs. Vet Rec. 1986 Jan 18;118(3):73-5. [Article]
- Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 6;163(23):698; author reply 698. [Article]
- Pott JM, Shov B: Monensin--tiamulin interactions in pigs. Vet Rec. 1981 Dec 12;109(24):545. [Article]
- Burch DG: Tiamulin activity against Brachyspira hyodysenteriae. Vet Rec. 2008 Dec 20-27;163(25):760. [Article]
- 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]
- Wanner M: [Tiamulin and salinomycin intolerance in swine]. Schweiz Arch Tierheilkd. 1984 Oct;126(10):521-6. [Article]
- Horrox NE: Monensin-tiamulin interaction risk to poultry. Vet Rec. 1980 Mar 22;106(12):278. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- KEGG Drug
- D06127
- KEGG Compound
- C12065
- ChemSpider
- 571196
- 1546410
- ChEBI
- 44137
- ChEMBL
- CHEMBL1234521
- ZINC
- ZINC000004217557
- PDBe Ligand
- MUL
- Wikipedia
- Tiamulin
- PDB Entries
- 1xbp / 8cgv / 8e41 / 8e42
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Solution Oral Injection, solution Granule, for solution Granule Oral 200 g/kg Granule Oral 100 g/kg Granule Oral Powder, for solution Powder Granule Oral 800 mg/g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.000524 mg/mL ALOGPS logP 4.47 ALOGPS logP 4.5 Chemaxon logS -6 ALOGPS pKa (Strongest Acidic) 14.43 Chemaxon pKa (Strongest Basic) 9.51 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.84 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 140.74 m3·mol-1 Chemaxon Polarizability 57.98 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 212.2568811 predictedDarkChem Lite v0.1.0 [M-H]- 203.02928 predictedDeepCCS 1.0 (2019) [M+H]+ 211.7757811 predictedDarkChem Lite v0.1.0 [M+H]+ 204.85419 predictedDeepCCS 1.0 (2019) [M+Na]+ 212.2386811 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.57121 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 19:00 / Updated at February 21, 2021 18:53