Thiamphenicol

Basic Info

Common NameThiamphenicol(F05964)
2D Structure
FRCD IDF05964
CAS Number15318-45-3
PubChem CID27200
FormulaC12H15Cl2NO5S
IUPAC Name

2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide

InChI Key

OTVAEFIXJLOWRX-NXEZZACHSA-N

InChI

InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

Canonical SMILES

CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O

Isomeric SMILES

CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O

Synonyms
        
            thiamphenicol
        
            15318-45-3
        
            Thiophenicol
        
            Thiamcol
        
            (+)-Thiamphenicol
        
            Raceophenidol
        
            Thiocymetin
        
            Dextrosulphenidol
        
            Thiamphenicolum
        
            D-Thiocymetin
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzenesulfonyl compounds
Intermediate Tree NodesNot available
Direct ParentBenzenesulfonyl compounds
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzenesulfonyl group - Sulfone - Sulfonyl - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid derivative - Alcohol - Aromatic alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary alcohol - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Alkyl halide - Alkyl chloride - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.

Properties

Property NameProperty Value
Molecular Weight356.214
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Complexity443
Monoisotopic Mass355.005
Exact Mass355.005
XLogP-0.3
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9383
Human Intestinal AbsorptionHIA+0.9310
Caco-2 PermeabilityCaco2-0.6100
P-glycoprotein SubstrateNon-substrate0.7574
P-glycoprotein InhibitorNon-inhibitor0.9489
Non-inhibitor0.9432
Renal Organic Cation TransporterNon-inhibitor0.9236
Distribution
Subcellular localizationMitochondria0.5160
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5856
CYP450 2D6 SubstrateNon-substrate0.8164
CYP450 3A4 SubstrateNon-substrate0.5896
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8529
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9972
Non-inhibitor0.9289
AMES ToxicityNon AMES toxic0.7181
CarcinogensNon-carcinogens0.6535
Fish ToxicityLow FHMT0.6448
Tetrahymena Pyriformis ToxicityHigh TPT0.6899
Honey Bee ToxicityLow HBT0.6274
BiodegradationReady biodegradable0.7060
Acute Oral ToxicityIII0.5991
Carcinogenicity (Three-class)Non-required0.6945
Model Value Unit
Absorption
Aqueous solubility-2.2124LogS
Caco-2 Permeability0.4964LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2718LD50, mol/kg
Fish Toxicity1.8372pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0484pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PerciformesJapan0.02ppm
Chicken,Edible OffalJapan0.02ppm
Chicken,KidneyJapan0.02ppm
Chicken,LiverJapan0.05ppm
Chicken,FatJapan0.04ppm
Chicken,MuscleJapan0.02ppm
MilkJapan0.05ppm
Pig,Edible OffalJapan0.02ppm
Cattle,Edible OffalJapan0.02ppm
Pig,KidneyJapan0.02ppm
Cattle,KidneyJapan0.02ppm
Pig,LiverJapan0.02ppm
Cattle,LiverJapan0.02ppm
Pig,FatJapan0.02ppm
Cattle,FatJapan0.02ppm
Pig,MuscleJapan0.02ppm
Cattle,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
Uptake and effects of the antimicrobial florfenicol, microplastics and their mixtures on freshwater exotic invasive bivalve Corbicula fluminea.Sci Total Environ2018 May 129890582
Distribution of Spiked Drugs between Milk Fat, Skim Milk, Whey, Curd, and MilkProtein Fractions: Expansion of Partitioning Models.J Agric Food Chem2018 Jan 1029271654
Screening method for the detection of residues of amphenicol antibiotics inbovine, ovine and porcine kidney by optical biosensor.Talanta2017 Sep 128602283
Advances on the chromatographic determination of amphenicols in food.Talanta2017 Jan 127837837
Deep eutectic solvents for the purification of chloromycetin and thiamphenicolfrom milk.J Sep Sci2017 Feb27888570
Determination of Residues of Phenicol Drugs in Ayu (Plecoglossus altivelis) byLC-MS/MS.Shokuhin Eiseigaku Zasshi201728690304
(Electro)Sensing of Phenicol Antibiotics-A Review.Crit Rev Food Sci Nutr2016 Oct 2525830490
Investigating the potential role of vitamin E in modulating the immunosuppressive effects of tylvalosin and florfenicol in broiler chickens.Res Vet Sci2016 Oct27663366
Development of magnetic molecularly imprinted polymers with double templates for the rapid and selective determination of amphenicol antibiotics in water, blood, and egg samples.J Chromatogr A2016 Nov 1827816223
UPLC-MS/MS determination of florfenicol and florfenicol amine antimicrobial residues in tilapia muscle.J Chromatogr B Analyt Technol Biomed Life Sci2016 Nov 127664336
Determination of chloramphenicol, thiamphenicol, florfenicol and florfenicolamine in poultry, swine, bovine and fish by liquid chromatography-tandem massspectrometry.J Chromatogr A2016 Jun 327133862
In situ solvothermal growth of metal-organic framework-ionic liquidfunctionalized graphene nanocomposite for highly efficient enrichment ofchloramphenicol and thiamphenicol.J Chromatogr A2016 Jan 426686562
Trace determination of antibacterial pharmaceuticals in fishes bymicrowave-assisted extraction and solid-phase purification combined withdispersive liquid-liquid microextraction followed by ultra-high performanceliquid chromatography-tandem mass spectrometry.J Chromatogr B Analyt Technol Biomed Life Sci2016 Feb 126773891
Selection and Identification of Chloramphenicol-Specific DNA Aptamers byMag-SELEX.Appl Biochem Biotechnol2016 Dec27613616
Determination of chloramphenicol, thiamphenicol and florfenicol in milk and honeyusing modified QuEChERS extraction coupled with polymeric monolith-basedcapillary liquid chromatography tandem mass spectrometry.Talanta2016 Apr 126838404
Evaluation and validation of a multi-residue method based on biochip technologyfor the simultaneous screening of six families of antibiotics in muscle andaquaculture products.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201626612266
Development of LC-MS/MS methodology for the detection/determination andconfirmation of chloramphenicol, chloramphenicol 3-O-β-d-glucuronide,florfenicol, florfenicol amine and thiamphenicol residues in bovine, equine andporcine liver.J Chromatogr B Analyt Technol Biomed Life Sci2015 Jun 125913426
Fast extraction of amphenicols residues from raw milk using novel fabric phasesorptive extraction followed by high-performance liquid chromatography-diodearray detection.Anal Chim Acta2015 Jan 1525542088
Approaches for the simultaneous detection of thiamphenicol, florfenicol andflorfenicol amine using immunochemical techniques.J Immunol Methods2013 Jul 3123587555
Development and validation of an HPLC method for the determination of sixpenicillin and three amphenicol antibiotics in gilthead seabream (Sparus Aurata) tissue according to the European Union Decision 2002/657/EC.Food Chem2013 Feb 1523194530