Thiamphenicol

Identification

Name
Thiamphenicol
Accession Number
DB08621
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
FLQ7571NPM
CAS number
15318-45-3
Weight
Average: 356.222
Monoisotopic: 355.004798699
Chemical Formula
C12H15Cl2NO5S
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
IUPAC Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
SMILES
[H][C@](CO)(NC(=O)C(Cl)Cl)[C@]([H])(O)C1=CC=C(C=C1)S(C)(=O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDr hemagglutinin structural subunitNot AvailableEscherichia coli
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 risk or severity of bleeding can be increased when Thiamphenicol is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Thiamphenicol is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Thiamphenicol is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Thiamphenicol 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 Thiamphenicol.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Thiamphenicol.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Thiamphenicol.
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 Thiamphenicol.
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 Thiamphenicol.
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 Thiamphenicol.
Food Interactions
Not Available

References

Synthesis Reference

Franco Pozzi, Claudia Tortora, Angelo Carenzi, "Pharmaceutical preparation containing thiamphenicol for veterinary use." U.S. Patent US4912138, issued January, 1979.

US4912138
General References
Not Available
External Links
KEGG Compound
C12853
PubChem Compound
27200
PubChem Substance
99445092
ChemSpider
25315
BindingDB
58925
ChEBI
32215
ChEMBL
CHEMBL1236282
HET
TH8
Wikipedia
Thiamphenicol
ATC Codes
J01BA52 — Thiamphenicol, combinationsJ01BA02 — Thiamphenicol
PDB Entries
2jkj

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.27 mg/mLALOGPS
logP0.33ALOGPS
logP-0.22ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.65ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.88 m3·mol-1ChemAxon
Polarizability32.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.931
Blood Brain Barrier+0.9383
Caco-2 permeable-0.61
P-glycoprotein substrateNon-substrate0.7574
P-glycoprotein inhibitor INon-inhibitor0.9489
P-glycoprotein inhibitor IINon-inhibitor0.9432
Renal organic cation transporterNon-inhibitor0.9236
CYP450 2C9 substrateNon-substrate0.5856
CYP450 2D6 substrateNon-substrate0.8164
CYP450 3A4 substrateNon-substrate0.5896
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8529
Ames testNon AMES toxic0.7181
CarcinogenicityNon-carcinogens0.6535
BiodegradationReady biodegradable0.706
Rat acute toxicity2.2718 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9972
hERG inhibition (predictor II)Non-inhibitor0.9289
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0649000000-3f7e62d09a29a445c8a6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-2931000000-1f1691e17ae627c7d762

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonyl compounds
Direct Parent
Benzenesulfonyl compounds
Alternative Parents
Sulfones / Secondary carboxylic acid amides / Secondary alcohols / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 2 more
Substituents
Benzenesulfonyl group / Sulfone / Sulfonyl / Carboxamide group / Secondary alcohol / Secondary carboxylic acid amide / Carboxylic acid derivative / Alcohol / Aromatic alcohol / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
sulfone, monocarboxylic acid amide (CHEBI:32215)

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Hemagglutinins of uropathogenic E.coli mediate adherence to the upper urinary tract. These adhesins bind to the Dr blood group antigen and also agglutinate human erythrocytes in the presence of D-m...
Gene Name
draA
Uniprot ID
P24093
Uniprot Name
Dr hemagglutinin structural subunit
Molecular Weight
17058.095 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:33 / Updated on November 02, 2018 06:51